Unnamed: 0
int64 0
445k
| level_0
int64 0
1.94M
| index
float64 0
1.81M
⌀ | original_rxn
stringlengths 104
2.67k
| fragments
stringlengths 6
161
⌀ | source
stringlengths 11
26
| year
int64 1.98k
2.02k
| mapped_rxn
stringlengths 110
2.63k
| confidence
float64 0
1
| canonical_rxn_with_fragment_info
stringlengths 25
599
| canonical_rxn
stringlengths 25
599
| ID
stringlengths 17
32
| reaction_hash
stringlengths 56
56
| reactants
stringlengths 55
1.33k
| products
stringlengths 51
1.3k
| retro_template
stringlengths 46
417
| template_hash
stringclasses 1k
values | selectivity
float64 0
1
| outcomes
float64 1
15
| reagents
stringlengths 1
370
⌀ | labels
int64 0
999
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
203,930 | 693,585 | 1,143,233 | [NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([C:27]5[N:28]([CH3:32])[CH:29]=[CH:30][N:31]=5)=[O:26])[C:19]=4[CH3:33])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[N:34]([CH:37]([CH3:39])[CH3:38])=[C:35]=[O:36]>ClCCCl>[CH:37]([NH:34][C:35](=[O:36])[NH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([C:27]5[N:28]([CH3:32])[CH:29]=[CH:30][N:31]=5)=[O:26])[C:19]=4[CH3:33])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1)([CH3:39])[CH3:38] | null | US08084620B2_0836 | 2,011 | ClCCCl.[C:30](=[O:31])=[N:32][CH:33]([CH3:34])[CH3:35].[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[n:8][cH:9][cH:10][n:11]2[CH3:12])[cH:13][cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21]([NH2:22])=[O:23])[c:24]2[nH:25][c:26]3[cH:27][c:28]([NH2:29])[cH:36][cH:37][c:38]3[c:39]12>>[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[n:8][cH:9][cH:10][n:11]2[CH3:12])[cH:13][cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21]([NH2:22])=[O:23])[c:24]2[nH:25][c:26]3[cH:27][c:28]([NH:29][C:30](=[O:31])[NH:32][CH:33]([CH3:34])[CH3:35])[cH:36][cH:37][c:38]3[c:39]12 | 0.772149 | CC(C)N=C=O.Cc1c(NC(=O)c2nccn2C)cccc1-c1ccc(C(N)=O)c2[nH]c3cc(N)ccc3c12.ClCCCl>>Cc1c(NC(=O)c2nccn2C)cccc1-c1ccc(C(N)=O)c2[nH]c3cc(NC(=O)NC(C)C)ccc3c12 | CC(C)N=C=O.Cc1c(NC(=O)c2nccn2C)cccc1-c1ccc(C(N)=O)c2[nH]c3cc(N)ccc3c12.ClCCCl>>Cc1c(NC(=O)c2nccn2C)cccc1-c1ccc(C(N)=O)c2[nH]c3cc(NC(=O)NC(C)C)ccc3c12 | US08084620B2_0836grants | 4f500e4e6b3a21e3c8d1d3c62f379c36d88b3c8064bed0d1fa322a58 | ClCCCl.[C:30](=[O:31])=[N:32][CH:33]([CH3:34])[CH3:35].[CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[n:8][cH:9][cH:10][n:11]2[CH3:12])[cH:13][cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21]([NH2:22])=[O:23])[c:24]2[nH:25][c:26]3[cH:27][c:28]([NH2:29])[cH:36][cH:37][c:38]3[c:39]12 | [CH3:1][c:2]1[c:3]([NH:4][C:5](=[O:6])[c:7]2[n:8][cH:9][cH:10][n:11]2[CH3:12])[cH:13][cH:14][cH:15][c:16]1-[c:17]1[cH:18][cH:19][c:20]([C:21]([NH2:22])=[O:23])[c:24]2[nH:25][c:26]3[cH:27][c:28]([NH:29][C:30](=[O:31])[NH:32][CH:33]([CH3:34])[CH3:35])[cH:36][cH:37][c:38]3[c:39]12 | ([C:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6])>>([C:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4]).([NH2;D1;+0:5]-[c:6]) | 94845dc1d958ca362d3949e0f9388da6fecc098bf241df3f6ab21a9c | 1 | 1 | ClCCCl | 176 |
438,721 | 1,898,523 | null | Br[C:2]1[CH:3]=[C:4]([C:16]#[N:17])[CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8]([C:12]([NH2:14])=[O:13])=[C:7]2[CH3:15].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:3]=[C:4]([C:16]#[N:17])[CH:5]=[C:6]3[C:10]=2[N:9]([CH3:11])[C:8]([C:12]([NH2:14])=[O:13])=[C:7]3[CH3:15])=[CH:21][CH:20]=1 | |f:2.3.4,7.8.9| | US20160185721A1_0186 | 2,016 | Br[c:10]1[c:9]2[n:7]([CH3:8])[c:3]([C:4]([NH2:5])=[O:6])[c:2]([CH3:1])[c:23]2[cH:22][c:19]([C:20]#[N:21])[cH:18]1.CC(=O)[O-].CC(=O)[O-].COCCOC.O=C([O-])[O-].OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1.[Na+].[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[n:7]([CH3:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[cH:18][c:19]([C:20]#[N:21])[cH:22][c:23]12 | 0.946748 | CC(=O)[O-]~CC(=O)[O-]~[Pd+2].COCCOC.Cc1c(C(N)=O)n(C)c2c(Br)cc(C#N)cc12.O=C([O-])[O-]~[Na+]~[Na+].OB(O)c1ccc(Cl)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1c(C(N)=O)n(C)c2c(-c3ccc(Cl)cc3)cc(C#N)cc12 | CC(=O)[O-].CC(=O)[O-].COCCOC.Cc1c(C(N)=O)n(C)c2c(Br)cc(C#N)cc12.O=C([O-])[O-].OB(O)c1ccc(Cl)cc1.[Na+].[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1c(C(N)=O)n(C)c2c(-c3ccc(Cl)cc3)cc(C#N)cc12 | US20160185721A1_0186apps | 3b4e1638ef507660bac6bf12ed8f7c4db61a99e4f1c38125376e4a4f | Br[c:10]1[c:9]2[n:7]([CH3:8])[c:3]([C:4]([NH2:5])=[O:6])[c:2]([CH3:1])[c:23]2[cH:22][c:19]([C:20]#[N:21])[cH:18]1.CC(=O)[O-].CC(=O)[O-].COCCOC.O=C([O-])[O-].OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1.[Na+].[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][c:2]1[c:3]([C:4]([NH2:5])=[O:6])[n:7]([CH3:8])[c:9]2[c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[cH:18][c:19]([C:20]#[N:21])[cH:22][c:23]12 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[c;H0;D3;+0:5](:[c:6]):[c:7])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).(O-B(-O)-[c;H0;D3;+0:5](:[c:6]):[c:7]) | d9e3b3a2cfe6e8e4f2db101af24fed0e1646b47d310510c8f6dc03e2 | 1 | 1 | CC(=O)[O-].CC(=O)[O-].COCCOC.O=C([O-])[O-].[Na+].[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 833 |
73,598 | 301,876 | 511,804 | C1(O[C:8](=[O:29])[NH:9][C:10]2[S:14][N:13]=[C:12]([O:15][CH2:16][C:17]3[CH:22]=[C:21]([F:23])[C:20]([CH3:24])=[CH:19][C:18]=3[F:25])[C:11]=2[C:26](=[O:28])[NH2:27])C=CC=CC=1.[NH2:30][CH2:31][CH2:32][CH:33]([OH:40])[CH2:34][NH:35][C:36]([CH3:39])([CH3:38])[CH3:37]>>[C:36]([NH:35][CH2:34][CH:33]([OH:40])[CH2:32][CH2:31][NH:30][C:8](=[O:29])[NH:9][C:10]1[S:14][N:13]=[C:12]([O:15][CH2:16][C:17]2[CH:22]=[C:21]([F:23])[C:20]([CH3:24])=[CH:19][C:18]=2[F:25])[C:11]=1[C:26]([NH2:27])=[O:28])([CH3:39])([CH3:37])[CH3:38] | null | US06235764B1_ | 2,001 | [NH2:16][CH2:17][CH2:18][CH:19]([OH:20])[CH2:21][NH:22][C:23]([CH3:24])([CH3:25])[CH3:26].c1ccc(O[C:14]([NH:13][c:12]2[s:11][n:10][c:9]([O:8][CH2:7][c:6]3[c:4]([F:5])[cH:3][c:2]([CH3:1])[c:32]([F:33])[cH:31]3)[c:27]2[C:28]([NH2:29])=[O:30])=[O:15])cc1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][O:8][c:9]2[n:10][s:11][c:12]([NH:13][C:14](=[O:15])[NH:16][CH2:17][CH2:18][CH:19]([OH:20])[CH2:21][NH:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]2[C:28]([NH2:29])=[O:30])[cH:31][c:32]1[F:33] | 0.451358 | CC(C)(C)NCC(O)CCN.Cc1cc(F)c(COc2nsc(NC(=O)Oc3ccccc3)c2C(N)=O)cc1F>>Cc1cc(F)c(COc2nsc(NC(=O)NCCC(O)CNC(C)(C)C)c2C(N)=O)cc1F | CC(C)(C)NCC(O)CCN.Cc1cc(F)c(COc2nsc(NC(=O)Oc3ccccc3)c2C(N)=O)cc1F>>Cc1cc(F)c(COc2nsc(NC(=O)NCCC(O)CNC(C)(C)C)c2C(N)=O)cc1F | US06235764B1_grants | 28be65af4fd06557b815e5b2ba201b8bac159b2df0691deb061ea314 | [NH2:16][CH2:17][CH2:18][CH:19]([OH:20])[CH2:21][NH:22][C:23]([CH3:24])([CH3:25])[CH3:26].c1ccc(O[C:14]([NH:13][c:12]2[s:11][n:10][c:9]([O:8][CH2:7][c:6]3[c:4]([F:5])[cH:3][c:2]([CH3:1])[c:32]([F:33])[cH:31]3)[c:27]2[C:28]([NH2:29])=[O:30])=[O:15])cc1 | [CH3:1][c:2]1[cH:3][c:4]([F:5])[c:6]([CH2:7][O:8][c:9]2[n:10][s:11][c:12]([NH:13][C:14](=[O:15])[NH:16][CH2:17][CH2:18][CH:19]([OH:20])[CH2:21][NH:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]2[C:28]([NH2:29])=[O:30])[cH:31][c:32]1[F:33] | ([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-c1:c:c:c:c:c:1).([C:4]-[NH2;D1;+0:5]) | f7a2680e4483e4b4927d48963101acffbdc36ec741b59f0518cc1da3 | 1 | 1 | null | 488 |
112,281 | 422,239 | 719,480 | [C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:14][CH3:15])=[C:7](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:8]=1)#[N:2].C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH2:45]([O:52][C:53](=[O:72])[CH2:54][C@@H:55]([NH2:71])[CH2:56][N:57]1[CH2:62][CH2:61][CH:60]([O:63][C:64]2[CH:69]=[CH:68][C:67]([F:70])=[CH:66][CH:65]=2)[CH2:59][CH2:58]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl>[CH2:45]([O:52][C:53](=[O:72])[CH2:54][C@@H:55]([NH:71][C:11](=[O:13])/[CH:10]=[CH:9]/[C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[O:14][CH3:15])[CH2:56][N:57]1[CH2:58][CH2:59][CH:60]([O:63][C:64]2[CH:65]=[CH:66][C:67]([F:70])=[CH:68][CH:69]=2)[CH2:61][CH2:62]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1 | |f:2.3| | US07034042B2_0120 | 2,006 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[B-](F)(F)F.O[C:13](/[CH:12]=[CH:11]/[c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9]1)=[O:14].[NH2:15][C@H:16]([CH2:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][N:29]1[CH2:30][CH2:31][CH:32]([O:33][c:34]2[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]2)[CH2:41][CH2:42]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][c:10]1/[CH:11]=[CH:12]/[C:13](=[O:14])[NH:15][C@H:16]([CH2:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][N:29]1[CH2:30][CH2:31][CH:32]([O:33][c:34]2[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]2)[CH2:41][CH2:42]1 | 0.804635 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[B-](F)(F)F.COc1ccc(C#N)cc1/C=C/C(=O)O.ClCCl.N[C@H](CC(=O)OCc1ccccc1)CN1CCC(Oc2ccc(F)cc2)CC1>>COc1ccc(C#N)cc1/C=C/C(=O)N[C@H](CC(=O)OCc1ccccc1)CN1CCC(Oc2ccc(F)cc2)CC1 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.COc1ccc(C#N)cc1/C=C/C(=O)O.ClCCl.F[B-](F)(F)F.N[C@H](CC(=O)OCc1ccccc1)CN1CCC(Oc2ccc(F)cc2)CC1>>COc1ccc(C#N)cc1/C=C/C(=O)N[C@H](CC(=O)OCc1ccccc1)CN1CCC(Oc2ccc(F)cc2)CC1 | US07034042B2_0120grants | 8e1b1b1276487a08f556577a1e0416bd350e517d2f1f7134c36fc790 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[B-](F)(F)F.O[C:13](/[CH:12]=[CH:11]/[c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9]1)=[O:14].[NH2:15][C@H:16]([CH2:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][N:29]1[CH2:30][CH2:31][CH:32]([O:33][c:34]2[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]2)[CH2:41][CH2:42]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][c:10]1/[CH:11]=[CH:12]/[C:13](=[O:14])[NH:15][C@H:16]([CH2:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH2:28][N:29]1[CH2:30][CH2:31][CH:32]([O:33][c:34]2[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]2)[CH2:41][CH2:42]1 | ([C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5]).([C:6]-[NH2;D1;+0:7]) | db3a97a0f595e9e42a12f3453ea056a3bcdbffe0b03ec342281970dd | 1 | 1 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.ClCCl.F[B-](F)(F)F | 767 |
225,153 | 755,000 | 1,244,002 | [CH3:1][C:2]1[C:20]([CH3:21])=[C:19]([N+:22]([O-])=O)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:16])[CH2:13][O:14][CH3:15])[CH:6]=1.CO.[H][H]>[Pt].CC(O)=O>[NH2:22][C:19]1[CH:18]=[CH:17][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:16])[CH2:13][O:14][CH3:15])[CH:6]=2)=[C:2]([CH3:1])[C:20]=1[CH3:21] | null | US08299074B2_0591 | 2,012 | CC(=O)O.CO.O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([O:10][c:9]2[cH:8][c:7]([NH:6][C:4]([CH2:3][O:2][CH3:1])=[O:5])[n:22][cH:21][cH:20]2)[c:18]([CH3:19])[c:16]1[CH3:17].[H][H].[Pt]>>[CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH2:15])[c:16]([CH3:17])[c:18]2[CH3:19])[cH:20][cH:21][n:22]1 | 0.985158 | CC(=O)O.CO.COCC(=O)Nc1cc(Oc2ccc([N+](=O)[O-])c(C)c2C)ccn1.[H][H].[Pt]>>COCC(=O)Nc1cc(Oc2ccc(N)c(C)c2C)ccn1 | CC(=O)O.CO.COCC(=O)Nc1cc(Oc2ccc([N+](=O)[O-])c(C)c2C)ccn1.[H][H].[Pt]>>COCC(=O)Nc1cc(Oc2ccc(N)c(C)c2C)ccn1 | US08299074B2_0591grants | 62c31aebed96312503d6b3cc1c0793f5b2ac2d1883605157e0278d41 | CC(=O)O.CO.O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([O:10][c:9]2[cH:8][c:7]([NH:6][C:4]([CH2:3][O:2][CH3:1])=[O:5])[n:22][cH:21][cH:20]2)[c:18]([CH3:19])[c:16]1[CH3:17].[H][H].[Pt] | [CH3:1][O:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH2:15])[c:16]([CH3:17])[c:18]2[CH3:19])[cH:20][cH:21][n:22]1 | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1) | 29ce6f8549b3eb39f0ff459e6dcee2e695f06f6055034d715c31e38e | 1 | 1 | CC(=O)O.CO.[H][H].[Pt] | 335 |
78,164 | 316,643 | 537,175 | [NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.[CH3:37][C:38]([CH3:40])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>>[C:25]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][NH:22][C:5]2[N:4]=[C:3]([CH2:2][NH:1][CH:38]([CH3:40])[CH3:37])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1 | |f:2.3| | US06326359B1_ | 2,001 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.O=[C:31]([CH3:32])[CH3:33].[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][CH:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[n:27][c:28]([CH2:29][NH2:30])[n:34][c:35]23)[C@H:36]([OH:37])[C@@H:38]1[OH:39].[Na+]>>[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][CH:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[n:27][c:28]([CH2:29][NH:30][CH:31]([CH3:32])[CH3:33])[n:34][c:35]23)[C@H:36]([OH:37])[C@@H:38]1[OH:39] | 0.337824 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].CC(C)=O.COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(CN)nc32)[C@H](O)[C@@H]1O>>COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(CNC(C)C)nc32)[C@H](O)[C@@H]1O | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)=O.COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(CN)nc32)[C@H](O)[C@@H]1O.[Na+]>>COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(CNC(C)C)nc32)[C@H](O)[C@@H]1O | US06326359B1_grants | 6b735eab35ece0fce34b0ab42495524c1ea49188401937b44ec617cc | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.O=[C:31]([CH3:32])[CH3:33].[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][CH:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[n:27][c:28]([CH2:29][NH2:30])[n:34][c:35]23)[C@H:36]([OH:37])[C@@H:38]1[OH:39].[Na+] | [CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][CH:14]([c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[n:27][c:28]([CH2:29][NH:30][CH:31]([CH3:32])[CH3:33])[n:34][c:35]23)[C@H:36]([OH:37])[C@@H:38]1[OH:39] | ([C:4]-[NH;D2;+0:5]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])>>(O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3]).([C:4]-[NH2;D1;+0:5]) | 67be25fd3ed7bf7f205940372151b70bd780167c6e07893adbc37ca7 | 1 | 1 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | 236 |
343,511 | 366,785 | null | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[C:20]([O:34][CH2:35][CH3:36])=[N:21][N:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[C:20]([O:34][CH2:35][CH3:36])=[N:21][N:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH:23]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | |f:1.2| | US20060148858A1_1378 | 2,006 | C1CCOC1.CC[O:31][C:29]([CH2:28][CH2:27][c:26]1[cH:25][cH:24][c:23]([O:22][CH2:21][CH2:20][CH2:19][c:18]2[c:4]([O:3][CH2:2][CH3:1])[n:5][n:6](-[c:7]3[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][n:16]3)[cH:17]2)[c:33]([O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:32]1)=[O:30].CO.Cl.[Na+].[OH-]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][n:16]2)[cH:17][c:18]1[CH2:19][CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]([CH2:27][CH2:28][C:29](=[O:30])[OH:31])[cH:32][c:33]1[O:34][CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1 | 0.276734 | C1CCOC1.CCOC(=O)CCc1ccc(OCCCc2cn(-c3ccc(C(F)(F)F)cn3)nc2OCC)c(OCc2ccccc2)c1.CO.Cl.[Na+]~[OH-]>>CCOc1nn(-c2ccc(C(F)(F)F)cn2)cc1CCCOc1ccc(CCC(=O)O)cc1OCc1ccccc1 | C1CCOC1.CCOC(=O)CCc1ccc(OCCCc2cn(-c3ccc(C(F)(F)F)cn3)nc2OCC)c(OCc2ccccc2)c1.CO.Cl.[Na+].[OH-]>>CCOc1nn(-c2ccc(C(F)(F)F)cn2)cc1CCCOc1ccc(CCC(=O)O)cc1OCc1ccccc1 | US20060148858A1_1378apps | 965fe63b0e73489fd57e8e95f05c801b8aeab7d55b9efb85f5bd012f | C1CCOC1.CC[O:31][C:29]([CH2:28][CH2:27][c:26]1[cH:25][cH:24][c:23]([O:22][CH2:21][CH2:20][CH2:19][c:18]2[c:4]([O:3][CH2:2][CH3:1])[n:5][n:6](-[c:7]3[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][n:16]3)[cH:17]2)[c:33]([O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:32]1)=[O:30].CO.Cl.[Na+].[OH-] | [CH3:1][CH2:2][O:3][c:4]1[n:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][n:16]2)[cH:17][c:18]1[CH2:19][CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]([CH2:27][CH2:28][C:29](=[O:30])[OH:31])[cH:32][c:33]1[O:34][CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | C1CCOC1.CO.Cl.[Na+].[OH-] | 7 |
336,985 | 237,711 | null | C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:11]=1[CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[C:25]([O:29][C:30]([NH:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([CH2:39][CH2:40][C:41](O)=[O:42])[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[Br:9][C:10]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:11]=1[CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([C:41](=[O:42])[CH2:40][CH2:39][C@H:36]2[CH2:35][CH2:34][C@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:38][CH2:37]2)[CH2:17][CH2:18]1 | |f:1.2,5.6| | US20050065140A1_0303 | 2,005 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O[C:14](=[O:15])[CH2:16][CH2:17][C@H:18]1[CH2:19][CH2:20][C@H:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]1.On1nnc2ccccc21.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([CH2:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:32][CH2:33]2)[cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[CH2:16][CH2:17][C@H:18]3[CH2:19][CH2:20][C@H:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[CH2:32][CH2:33]2)[cH:34]1 | 0.298281 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](CCC(=O)O)CC1.CCN(CC)CC.CCN=C=NCCCN(C)C~Cl.CN(C)C=O.COc1ccc(Br)c(CC2CCNCC2)c1~Cl.O.On1nnc2ccccc21>>COc1ccc(Br)c(CC2CCN(C(=O)CC[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)CC2)c1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](CCC(=O)O)CC1.CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.COc1ccc(Br)c(CC2CCNCC2)c1.Cl.Cl.O.On1nnc2ccccc21>>COc1ccc(Br)c(CC2CCN(C(=O)CC[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)CC2)c1 | US20050065140A1_0303apps | e4e381a2fd480ce470e30de09f634f958c826dfffbfb32b5d0a53f61 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.O[C:14](=[O:15])[CH2:16][CH2:17][C@H:18]1[CH2:19][CH2:20][C@H:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]1.On1nnc2ccccc21.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([CH2:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:32][CH2:33]2)[cH:34]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[CH2:16][CH2:17][C@H:18]3[CH2:19][CH2:20][C@H:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[CH2:32][CH2:33]2)[cH:34]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O.On1nnc2ccccc21 | 146 |
227,833 | 763,260 | 1,257,832 | [CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:26])[C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[N:16][CH:15]=3)[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].Br[C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][C:29]=1[Cl:37].C(C1C=C(NC(C2C=CC(N3CCN(C4C=CC(C(O)=O)=CC=4)CC3)=C(F)C=2)=O)C=CC=1)(C)(C)C>>[Cl:37][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:28]=1[N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:18]=[CH:19][C:14]([C:13](=[O:26])[NH:12][C:9]3[CH:10]=[C:11]4[C:6]([CH:5]=[CH:4][N:3]4[CH2:1][CH3:2])=[CH:7][CH:8]=3)=[CH:15][N:16]=2)[CH2:21][CH2:22]1)[C:32]([OH:34])=[O:33] | null | US08324385B2_0501 | 2,012 | Br[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][c:29]1[Cl:30].CC(C)(C)c1cccc(NC(=O)c2ccc(N3CCN(c4ccc(C(=O)O)cc4)CC3)c(F)c2)c1.[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[cH:14][cH:15][c:16]([N:17]4[CH2:18][CH2:19][NH:20][CH2:31][CH2:32]4)[n:33][cH:34]3)[cH:35][c:36]12>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[cH:14][cH:15][c:16]([N:17]4[CH2:18][CH2:19][N:20]([c:21]5[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][c:29]5[Cl:30])[CH2:31][CH2:32]4)[n:33][cH:34]3)[cH:35][c:36]12 | 0.693823 | CC(C)(C)c1cccc(NC(=O)c2ccc(N3CCN(c4ccc(C(=O)O)cc4)CC3)c(F)c2)c1.CCn1ccc2ccc(NC(=O)c3ccc(N4CCNCC4)nc3)cc21.O=C(O)c1ccc(Br)c(Cl)c1>>CCn1ccc2ccc(NC(=O)c3ccc(N4CCN(c5ccc(C(=O)O)cc5Cl)CC4)nc3)cc21 | CC(C)(C)c1cccc(NC(=O)c2ccc(N3CCN(c4ccc(C(=O)O)cc4)CC3)c(F)c2)c1.CCn1ccc2ccc(NC(=O)c3ccc(N4CCNCC4)nc3)cc21.O=C(O)c1ccc(Br)c(Cl)c1>>CCn1ccc2ccc(NC(=O)c3ccc(N4CCN(c5ccc(C(=O)O)cc5Cl)CC4)nc3)cc21 | US08324385B2_0501grants | 4d5cf1e27ce0d3b84529cc76498c603ea2f3beef3408c8452f4a7096 | Br[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][c:29]1[Cl:30].CC(C)(C)c1cccc(NC(=O)c2ccc(N3CCN(c4ccc(C(=O)O)cc4)CC3)c(F)c2)c1.[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[cH:14][cH:15][c:16]([N:17]4[CH2:18][CH2:19][NH:20][CH2:31][CH2:32]4)[n:33][cH:34]3)[cH:35][c:36]12 | [CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[cH:14][cH:15][c:16]([N:17]4[CH2:18][CH2:19][N:20]([c:21]5[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][c:29]5[Cl:30])[CH2:31][CH2:32]4)[n:33][cH:34]3)[cH:35][c:36]12 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | dd2fdbd233407626d24330af0096988c30d6471ee9a6e9d629c560da | 1 | 1 | CC(C)(C)c1cccc(NC(=O)c2ccc(N3CCN(c4ccc(C(=O)O)cc4)CC3)c(F)c2)c1 | 294 |
251,631 | 834,154 | 1,383,801 | [C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].C(Cl)(=O)C(Cl)=O.[C:33]1([C@@H:39]([CH3:42])[CH2:40][NH2:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1C=CC=CC=1>ClCCl.CN(C=O)C.CN(C)C1C=CN=CC=1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](=[O:20])[NH:41][CH2:40][C@@H:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:42])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2] | null | US08569522B2_1032 | 2,013 | CN(C)C=O.CN(C)c1ccncc1.ClCCl.O=C(Cl)C(=O)Cl.O[C:17]([c:16]1[cH:15][cH:14][c:13]([O:12][c:11]2[cH:10][c:9]3[c:35]([cH:34][c:31]2[C:32]#[N:33])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][O:8]3)[cH:30][cH:29]1)=[O:18].[NH2:19][CH2:20][C@H:21]([CH3:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.c1ccncc1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][O:8][c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][C@H:21]([CH3:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30]3)[c:31]([C:32]#[N:33])[cH:34][c:35]21 | 0.884252 | CN(C)C=O.CN(C)c1ccncc1.COC(=O)C1CCOc2cc(Oc3ccc(C(=O)O)cc3)c(C#N)cc21.C[C@@H](CN)c1ccccc1.ClCCl.O=C(Cl)C(=O)Cl.c1ccncc1>>COC(=O)C1CCOc2cc(Oc3ccc(C(=O)NC[C@H](C)c4ccccc4)cc3)c(C#N)cc21 | CN(C)C=O.CN(C)c1ccncc1.COC(=O)C1CCOc2cc(Oc3ccc(C(=O)O)cc3)c(C#N)cc21.C[C@@H](CN)c1ccccc1.ClCCl.O=C(Cl)C(=O)Cl.c1ccncc1>>COC(=O)C1CCOc2cc(Oc3ccc(C(=O)NC[C@H](C)c4ccccc4)cc3)c(C#N)cc21 | US08569522B2_1032grants | 6ce3db96fe7beb208ee3ec51791f54232cafb47cc7cad54ca59b9a34 | CN(C)C=O.CN(C)c1ccncc1.ClCCl.O=C(Cl)C(=O)Cl.O[C:17]([c:16]1[cH:15][cH:14][c:13]([O:12][c:11]2[cH:10][c:9]3[c:35]([cH:34][c:31]2[C:32]#[N:33])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][O:8]3)[cH:30][cH:29]1)=[O:18].[NH2:19][CH2:20][C@H:21]([CH3:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.c1ccncc1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][O:8][c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][c:16]([C:17](=[O:18])[NH:19][CH2:20][C@H:21]([CH3:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30]3)[c:31]([C:32]#[N:33])[cH:34][c:35]21 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | CN(C)C=O.CN(C)c1ccncc1.ClCCl.O=C(Cl)C(=O)Cl.c1ccncc1 | 334 |
411,096 | 1,647,312 | null | [Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[N:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]1[C:26](=[O:27])[N:25]([CH2:28][C:29](O)=[O:30])[C:18]2[N:19]=[C:20]([NH:23][CH3:24])[N:21]=[CH:22][C:17]=2[CH:16]=1.[OH:32][CH:33]1[CH2:37][CH2:36][NH:35][CH2:34]1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[N:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([N:35]2[CH2:36][CH2:37][CH:33]([OH:32])[CH2:34]2)=[O:30])[C:18]2[N:19]=[C:20]([NH:23][CH3:24])[N:21]=[CH:22][C:17]=2[CH:16]=1 | null | US20150031674A1_0544 | 2,015 | O[C:27]([CH2:26][n:25]1[c:23](=[O:24])[c:8](-[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][cH:16][c:17]([CH3:18])[n:19]3)[cH:20][c:21]2[Cl:22])[cH:7][c:6]2[cH:5][n:4][c:3]([NH:2][CH3:1])[n:36][c:35]21)=[O:28].[NH:29]1[CH2:30][CH2:31][CH:32]([OH:33])[CH2:34]1>>[CH3:1][NH:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][n:15][cH:16][c:17]([CH3:18])[n:19]4)[cH:20][c:21]3[Cl:22])[c:23](=[O:24])[n:25]([CH2:26][C:27](=[O:28])[N:29]3[CH2:30][CH2:31][CH:32]([OH:33])[CH2:34]3)[c:35]2[n:36]1 | 0.926898 | CNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(CC(=O)O)c2n1.OC1CCNC1>>CNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(CC(=O)N3CCC(O)C3)c2n1 | CNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(CC(=O)O)c2n1.OC1CCNC1>>CNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(CC(=O)N3CCC(O)C3)c2n1 | US20150031674A1_0544apps | 360646b5f86f48c08cf617e734b53616a51a813148e12fcf4a629660 | O[C:27]([CH2:26][n:25]1[c:23](=[O:24])[c:8](-[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][cH:16][c:17]([CH3:18])[n:19]3)[cH:20][c:21]2[Cl:22])[cH:7][c:6]2[cH:5][n:4][c:3]([NH:2][CH3:1])[n:36][c:35]21)=[O:28].[NH:29]1[CH2:30][CH2:31][CH:32]([OH:33])[CH2:34]1 | [CH3:1][NH:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][n:15][cH:16][c:17]([CH3:18])[n:19]4)[cH:20][c:21]3[Cl:22])[c:23](=[O:24])[n:25]([CH2:26][C:27](=[O:28])[N:29]3[CH2:30][CH2:31][CH:32]([OH:33])[CH2:34]3)[c:35]2[n:36]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | null | 146 |
164,708 | 579,912 | 964,915 | Br[CH2:2][CH2:3][CH2:4][Si:5]([CH3:35])([CH3:34])[CH2:6][CH2:7][C:8]1[C:20]2[CH2:19][N:18]3[C:13](=[CH:14][C:15]4[C@:25]([CH2:27][CH3:28])([OH:26])[C:24](=[O:29])[O:23][CH2:22][C:16]=4[C:17]3=[O:21])[C:12]=2[N:11]=[C:10]2[CH:30]=[CH:31][CH:32]=[CH:33][C:9]=12.[NH:36]1[CH:40]=[CH:39][N:38]=[CH:37]1>CN(C)C=O>[CH2:27]([C@:25]1([OH:26])[C:15]2[CH:14]=[C:13]3[N:18]([C:17](=[O:21])[C:16]=2[CH2:22][O:23][C:24]1=[O:29])[CH2:19][C:20]1[C:8]([CH2:7][CH2:6][Si:5]([CH2:4][CH2:3][CH2:2][N:36]2[CH:40]=[CH:39][N:38]=[CH:37]2)([CH3:34])[CH3:35])=[C:9]2[CH:33]=[CH:32][CH:31]=[CH:30][C:10]2=[N:11][C:12]3=1)[CH3:28] | null | US07687496B2_0166 | 2,010 | Br[CH2:34][CH2:33][CH2:32][Si:29]([CH2:28][CH2:27][c:26]1[c:17]2[c:18]([n:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]31)-[c:12]1[cH:11][c:10]3[c:9]([c:14](=[O:15])[n:13]1[CH2:16]2)[CH2:8][O:7][C:5](=[O:6])[C@@:3]3([CH2:2][CH3:1])[OH:4])([CH3:30])[CH3:31].CN(C)C=O.[nH:35]1[cH:36][cH:37][n:38][cH:39]1>>[CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[c:18]-1[n:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[c:26]2[CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH2:32][CH2:33][CH2:34][n:35]1[cH:36][cH:37][n:38][cH:39]1 | 0.701244 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccccc1c2CC[Si](C)(C)CCCBr.CN(C)C=O.c1c[nH]cn1>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccccc1c2CC[Si](C)(C)CCCn1ccnc1 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccccc1c2CC[Si](C)(C)CCCBr.CN(C)C=O.c1c[nH]cn1>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccccc1c2CC[Si](C)(C)CCCn1ccnc1 | US07687496B2_0166grants | 3fa8f9ec4e4bd4b339f3e9d13394d3146c423c6f53c4886274246da7 | Br[CH2:34][CH2:33][CH2:32][Si:29]([CH2:28][CH2:27][c:26]1[c:17]2[c:18]([n:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]31)-[c:12]1[cH:11][c:10]3[c:9]([c:14](=[O:15])[n:13]1[CH2:16]2)[CH2:8][O:7][C:5](=[O:6])[C@@:3]3([CH2:2][CH3:1])[OH:4])([CH3:30])[CH3:31].CN(C)C=O.[nH:35]1[cH:36][cH:37][n:38][cH:39]1 | [CH3:1][CH2:2][C@@:3]1([OH:4])[C:5](=[O:6])[O:7][CH2:8][c:9]2[c:10]1[cH:11][c:12]1[n:13]([c:14]2=[O:15])[CH2:16][c:17]2[c:18]-1[n:19][c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[c:26]2[CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH2:32][CH2:33][CH2:34][n:35]1[cH:36][cH:37][n:38][cH:39]1 | ([C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:6]1:[c:5]:[c:4]:[#7;a:3]:[c:7]:1)>>(Br-[CH2;D2;+0:1]-[C:2]).([#7;a:3]1:[c:4]:[c:5]:[nH;D2;+0:6]:[c:7]:1) | f5900f9aaf1f8d14477b77ff003f26cd2a7fff09608cd211f57e2398 | 1 | 1 | CN(C)C=O | 495 |
240,756 | 802,418 | 1,328,668 | [CH2:1]([NH:3][C:4](=[O:11])[NH:5][O:6][CH2:7][C:8]([OH:10])=O)[CH3:2].[NH2:12][C@@H:13]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:40][CH:39]=1)[C:14]([N:16]([C@@H:28]([CH3:36])[CH:29]([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])[CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)=[O:15]>>[C:45]([O:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][C@H:13]([NH:12][C:8](=[O:10])[CH2:7][O:6][NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:11])[C:14]([N:16]([C@@H:28]([CH3:36])[CH:29]([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])[CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:43][CH:42]=1)([CH3:48])([CH3:46])[CH3:47] | null | US08455488B2_0499 | 2,013 | O[C:9]([CH2:8][O:7][NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])=[O:10].[NH2:11][C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1)[C:25](=[O:26])[N:27]([CH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12)[C@@H:39]([CH3:40])[CH:41]([O:42][CH2:43][CH3:44])[O:45][CH2:46][CH3:47]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][O:7][CH2:8][C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1)[C:25](=[O:26])[N:27]([CH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12)[C@@H:39]([CH3:40])[CH:41]([O:42][CH2:43][CH3:44])[O:45][CH2:46][CH3:47] | 0.221045 | CCNC(=O)NOCC(=O)O.CCOC(OCC)[C@H](C)N(Cc1cccc2ccccc12)C(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1>>CCNC(=O)NOCC(=O)N[C@@H](Cc1ccc(OC(C)(C)C)cc1)C(=O)N(Cc1cccc2ccccc12)[C@@H](C)C(OCC)OCC | CCNC(=O)NOCC(=O)O.CCOC(OCC)[C@H](C)N(Cc1cccc2ccccc12)C(=O)[C@@H](N)Cc1ccc(OC(C)(C)C)cc1>>CCNC(=O)NOCC(=O)N[C@@H](Cc1ccc(OC(C)(C)C)cc1)C(=O)N(Cc1cccc2ccccc12)[C@@H](C)C(OCC)OCC | US08455488B2_0499grants | b7cf73f231bde5013e55e4c084bd72eb49856cb2847bb28782dfb6d7 | O[C:9]([CH2:8][O:7][NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])=[O:10].[NH2:11][C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1)[C:25](=[O:26])[N:27]([CH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12)[C@@H:39]([CH3:40])[CH:41]([O:42][CH2:43][CH3:44])[O:45][CH2:46][CH3:47] | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][O:7][CH2:8][C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1)[C:25](=[O:26])[N:27]([CH2:28][c:29]1[cH:30][cH:31][cH:32][c:33]2[cH:34][cH:35][cH:36][cH:37][c:38]12)[C@@H:39]([CH3:40])[CH:41]([O:42][CH2:43][CH3:44])[O:45][CH2:46][CH3:47] | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8]) | 09e961e4c21b1adcf2f8d3b116773699ab5020ae114ca5b853caf10a | 1 | 1 | null | 133 |
240,046 | 800,008 | 1,324,191 | [OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[CH:7]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([Cl:27])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[O:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:15][CH2:16]3)=[O:13])[N:10]=2)[CH:7]=1 | |f:2.3.4| | US08445509B2_1055 | 2,013 | CS(C)=O.F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([Cl:18])[cH:19]1.O=C([O-])[O-].[Cs+].[Cs+].[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[cH:7][c:8]([OH:9])[cH:20][cH:21][c:22]2[n:23]1)[CH:24]1[CH2:25][CH2:26]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[cH:7][c:8]([O:9][c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([Cl:18])[cH:19]3)[cH:20][cH:21][c:22]2[n:23]1)[CH:24]1[CH2:25][CH2:26]1 | 0.880487 | CS(C)=O.O=C(Nc1cn2cc(O)ccc2n1)C1CC1.O=C([O-])[O-]~[Cs+]~[Cs+].O=[N+]([O-])c1ccc(F)cc1Cl>>O=C(Nc1cn2cc(Oc3ccc([N+](=O)[O-])c(Cl)c3)ccc2n1)C1CC1 | CS(C)=O.O=C(Nc1cn2cc(O)ccc2n1)C1CC1.O=C([O-])[O-].O=[N+]([O-])c1ccc(F)cc1Cl.[Cs+].[Cs+]>>O=C(Nc1cn2cc(Oc3ccc([N+](=O)[O-])c(Cl)c3)ccc2n1)C1CC1 | US08445509B2_1055grants | dfcf1fa1f0e493941fe4d39590adca9dcf8035fdaad3e4afbb14fb98 | CS(C)=O.F[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([Cl:18])[cH:19]1.O=C([O-])[O-].[Cs+].[Cs+].[O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[cH:7][c:8]([OH:9])[cH:20][cH:21][c:22]2[n:23]1)[CH:24]1[CH2:25][CH2:26]1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][n:6]2[cH:7][c:8]([O:9][c:10]3[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([Cl:18])[cH:19]3)[cH:20][cH:21][c:22]2[n:23]1)[CH:24]1[CH2:25][CH2:26]1 | ([#7;a:4]:[c:5]:[c:6]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([#7;a:4]:[c:5]:[c:6]-[OH;D1;+0:7]) | 1c76728524b4f31272bf7eea18e8145c7497f7523e3bfa0eac138003 | 1 | 1 | CS(C)=O.O=C([O-])[O-].[Cs+].[Cs+] | 845 |
303,719 | 987,402 | 1,665,619 | C[O:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[OH-].[Na+]>CO>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:9]([CH3:10])[O:8][N:7]=1 | |f:1.2| | US09132126B2_0115 | 2,015 | CO.C[O:16][C:14]([c:13]1[c:2]([CH3:1])[o:3][n:4][c:5]1-[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12])=[O:15].[Na+].[OH-]>>[CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[Cl:12])[c:13]1[C:14](=[O:15])[OH:16] | 0.951451 | CO.COC(=O)c1c(-c2ccccc2Cl)noc1C.[Na+]~[OH-]>>Cc1onc(-c2ccccc2Cl)c1C(=O)O | CO.COC(=O)c1c(-c2ccccc2Cl)noc1C.[Na+].[OH-]>>Cc1onc(-c2ccccc2Cl)c1C(=O)O | US09132126B2_0115grants | a5775368ad7a3d23b3eeb39197fd5009b2c89fb7f5fc249d1afa6ff2 | CO.C[O:16][C:14]([c:13]1[c:2]([CH3:1])[o:3][n:4][c:5]1-[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12])=[O:15].[Na+].[OH-] | [CH3:1][c:2]1[o:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[Cl:12])[c:13]1[C:14](=[O:15])[OH:16] | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b499e0b68ab8cc89df665c73ba592c6e17427fbd5b75a0a04b8fb5db | 1 | 1 | CO.[Na+].[OH-] | 152 |
105,771 | 402,838 | 688,067 | [F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:31][CH2:30][CH:29]([C:32](O)=[O:33])[CH2:28][CH2:27]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.C(Cl)CCl.[NH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:31][CH2:30][CH:29]([C:32]([N:42]6[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]6)=[O:33])[CH2:28][CH2:27]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1 | null | US06908916B2_0123 | 2,005 | CN(C)c1ccncc1.ClCCCl.ClCCl.O[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][n:11]3[n:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22][n:23][n:24]5[CH2:25][c:26]5[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]5)[cH:33]4)[c:34]23)[CH2:35][CH2:36]1.[NH:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]1>>[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][n:11]3[n:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22][n:23][n:24]5[CH2:25][c:26]5[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]5)[cH:33]4)[c:34]23)[CH2:35][CH2:36]1)[N:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]1 | 0.543131 | C1CNCCN1.CN(C)c1ccncc1.ClCCCl.ClCCl.O=C(O)C1CCN(Cc2ccn3ncnc(Nc4ccc5c(cnn5Cc5cccc(F)c5)c4)c23)CC1>>O=C(C1CCN(Cc2ccn3ncnc(Nc4ccc5c(cnn5Cc5cccc(F)c5)c4)c23)CC1)N1CCNCC1 | C1CNCCN1.CN(C)c1ccncc1.ClCCCl.ClCCl.O=C(O)C1CCN(Cc2ccn3ncnc(Nc4ccc5c(cnn5Cc5cccc(F)c5)c4)c23)CC1>>O=C(C1CCN(Cc2ccn3ncnc(Nc4ccc5c(cnn5Cc5cccc(F)c5)c4)c23)CC1)N1CCNCC1 | US06908916B2_0123grants | a224fb399097baefa184d2511bfaaed2eb6fff5f57ffb567f7e12d22 | CN(C)c1ccncc1.ClCCCl.ClCCl.O[C:2](=[O:1])[CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][n:11]3[n:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22][n:23][n:24]5[CH2:25][c:26]5[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]5)[cH:33]4)[c:34]23)[CH2:35][CH2:36]1.[NH:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]1 | [O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][n:11]3[n:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][c:20]5[c:21]([cH:22][n:23][n:24]5[CH2:25][c:26]5[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]5)[cH:33]4)[c:34]23)[CH2:35][CH2:36]1)[N:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CN(C)c1ccncc1.ClCCCl.ClCCl | 146 |
173,745 | 607,590 | 1,007,748 | Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([CH2:17][CH3:18])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16].[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1>>[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3([CH2:17][CH3:18])[C:14]4[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=4)[NH:8][C:7]3=[O:16])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1 | null | US07786129B2_0750 | 2,010 | Cl[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([CH2:2][CH3:1])[C:21](=[O:22])[NH:23][c:24]2[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]21.[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][CH2:2][C:3]1([CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[CH2:19][CH2:20]2)[C:21](=[O:22])[NH:23][c:24]2[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]21 | 0.938182 | CCC1(CCCCCl)C(=O)Nc2cc(F)ccc21.Clc1cccc(N2CCNCC2)c1>>CCC1(CCCCN2CCN(c3cccc(Cl)c3)CC2)C(=O)Nc2cc(F)ccc21 | CCC1(CCCCCl)C(=O)Nc2cc(F)ccc21.Clc1cccc(N2CCNCC2)c1>>CCC1(CCCCN2CCN(c3cccc(Cl)c3)CC2)C(=O)Nc2cc(F)ccc21 | US07786129B2_0750grants | 7ce4e64f4b3fbc8d4831ec8262ac29c5b7a19173b1be5ea5fbbf0493 | Cl[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1([CH2:2][CH3:1])[C:21](=[O:22])[NH:23][c:24]2[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]21.[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[CH2:19][CH2:20]1 | [CH3:1][CH2:2][C:3]1([CH2:4][CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]3)[CH2:19][CH2:20]2)[C:21](=[O:22])[NH:23][c:24]2[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]21 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(Cl-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | c38df6bb72f417e54d2346e687e032ed86554f208af48effa9422912 | 0.5 | 2 | null | 138 |
66,316 | 277,318 | 470,623 | [CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:30])[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].ClC1C=CC=C(C(OO)=[O:39])C=1.[K+].[Br-]>ClCCl>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:30])[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:24][C:18]=3[N:17]=2)=[O:39])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13] | |f:2.3| | US06051570_ | 2,000 | ClCCl.O=C(O[OH:16])c1cccc(Cl)c1.[Br-].[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][c:13]1[CH2:14][S:15][c:17]1[n:18][c:19]2[cH:20][c:21](-[n:22]3[cH:23][cH:24][n:25][cH:26]3)[c:27]([F:28])[cH:29][c:30]2[nH:31]1.[K+]>>[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][c:13]1[CH2:14][S:15](=[O:16])[c:17]1[n:18][c:19]2[cH:20][c:21](-[n:22]3[cH:23][cH:24][n:25][cH:26]3)[c:27]([F:28])[cH:29][c:30]2[nH:31]1 | 0.221045 | Cc1c(OCC(F)(F)F)ccnc1CSc1nc2cc(-n3ccnc3)c(F)cc2[nH]1.ClCCl.O=C(OO)c1cccc(Cl)c1.[Br-]~[K+]>>Cc1c(OCC(F)(F)F)ccnc1CS(=O)c1nc2cc(-n3ccnc3)c(F)cc2[nH]1 | Cc1c(OCC(F)(F)F)ccnc1CSc1nc2cc(-n3ccnc3)c(F)cc2[nH]1.ClCCl.O=C(OO)c1cccc(Cl)c1.[Br-].[K+]>>Cc1c(OCC(F)(F)F)ccnc1CS(=O)c1nc2cc(-n3ccnc3)c(F)cc2[nH]1 | US06051570_grants | f5678441391706355ab9a32f311b28f91512874ea18361f64dbd5d78 | ClCCl.O=C(O[OH:16])c1cccc(Cl)c1.[Br-].[CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][c:13]1[CH2:14][S:15][c:17]1[n:18][c:19]2[cH:20][c:21](-[n:22]3[cH:23][cH:24][n:25][cH:26]3)[c:27]([F:28])[cH:29][c:30]2[nH:31]1.[K+] | [CH3:1][c:2]1[c:3]([O:4][CH2:5][C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][n:12][c:13]1[CH2:14][S:15](=[O:16])[c:17]1[n:18][c:19]2[cH:20][c:21](-[n:22]3[cH:23][cH:24][n:25][cH:26]3)[c:27]([F:28])[cH:29][c:30]2[nH:31]1 | ([#7;a:2]:[c:3](:[#7;a:4])-[S;H0;D3;+0:5](-[C:6])=[O;H0;D1;+0:1])>>(Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1).([#7;a:2]:[c:3](:[#7;a:4])-[S;H0;D2;+0:5]-[C:6]) | 495da876474ee730446ebecf495930fc309da40c6a68cbb56d47fb3b | 1 | 1 | ClCCl.[Br-].[K+] | 595 |
335,392 | 213,543 | null | [CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([OH:13])[CH:9]=[CH:8]2)=[CH2:2].N1C=CN=C1.Cl[Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22].O>CN(C)C=O>[CH:21]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[O:13][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:3]([CH:1]=[CH2:2])[CH:4]=[CH:5][CH:6]=2)[CH:11]=1)([CH3:23])[CH3:22] | null | US20040259875A1_0296 | 2,004 | CN(C)C=O.Cl[Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21].O.[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:22][c:23]12.c1c[nH]cn1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][c:10]([O:11][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21])[cH:22][c:23]12 | 0.093034 | C=Cc1cccc2ccc(O)cc12.CC(C)[Si](Cl)(C(C)C)C(C)C.CN(C)C=O.O.c1c[nH]cn1>>C=Cc1cccc2ccc(O[Si](C(C)C)(C(C)C)C(C)C)cc12 | C=Cc1cccc2ccc(O)cc12.CC(C)[Si](Cl)(C(C)C)C(C)C.CN(C)C=O.O.c1c[nH]cn1>>C=Cc1cccc2ccc(O[Si](C(C)C)(C(C)C)C(C)C)cc12 | US20040259875A1_0296apps | 1b817cf2abc693cf494a83e96db179e2ddb852a1eb073928ebda0230 | CN(C)C=O.Cl[Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21].O.[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:22][c:23]12.c1c[nH]cn1 | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[cH:8][cH:9][c:10]([O:11][Si:12]([CH:13]([CH3:14])[CH3:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21])[cH:22][c:23]12 | ([C:2]-[Si;H0;D4;+0:1](-[C:3])(-[C:4])-[O;H0;D2;+0:5]-[c:6])>>(Cl-[Si;H0;D4;+0:1](-[C:2])(-[C:3])-[C:4]).([OH;D1;+0:5]-[c:6]) | 78671a61751fb41a7735eaf781f047ef571d6531544684af2f680407 | 1 | 1 | CN(C)C=O.O.c1c[nH]cn1 | 746 |
132,555 | 482,856 | 813,720 | [F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@H:7]([C:15]([NH2:17])=O)[CH2:6][C:5]2=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][C@H:7]([CH2:15][NH2:17])[CH2:6][C:5]2=1 | |f:1.2.3.4.5.6| | US07297704B2_0284 | 2,007 | C1CCOC1.O=[C:2]([NH2:1])[C@H:3]1[CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[c:15]2[CH2:16]1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[NH2:1][CH2:2][C@H:3]1[CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[c:15]2[CH2:16]1 | 0.991932 | C1CCOC1.NC(=O)[C@H]1CCc2[nH]c3ccc(F)cc3c2C1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>NC[C@H]1CCc2[nH]c3ccc(F)cc3c2C1 | C1CCOC1.NC(=O)[C@H]1CCc2[nH]c3ccc(F)cc3c2C1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>NC[C@H]1CCc2[nH]c3ccc(F)cc3c2C1 | US07297704B2_0284grants | 58e841a674345a6f603590ca3c03070fdf606636c1dff5b89107a956 | C1CCOC1.O=[C:2]([NH2:1])[C@H:3]1[CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[c:15]2[CH2:16]1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [NH2:1][CH2:2][C@H:3]1[CH2:4][CH2:5][c:6]2[nH:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[c:15]2[CH2:16]1 | ([C:2]-[CH2;D2;+0:1]-[N;D1;H2:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[N;D1;H2:3]) | 164bcd5926595fb14a6a9bdfa6263711f1e81657ce47f1a9ea439ccb | 1 | 1 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 112 |
256,664 | 849,623 | 1,413,120 | [NH2:1][N:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:19].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1>>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:1][N:2]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:19])=[O:29])=[CH:23][CH:22]=1 | null | US08629143B2_0571 | 2,014 | O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.[NH2:11][n:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1=[O:29]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[NH:11][n:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1=[O:29] | 0.878732 | Nn1nc(-c2ccc(F)cc2)c2ccccc2c1=O.O=C(O)Cc1ccc(Cl)cc1>>O=C(Cc1ccc(Cl)cc1)Nn1nc(-c2ccc(F)cc2)c2ccccc2c1=O | Nn1nc(-c2ccc(F)cc2)c2ccccc2c1=O.O=C(O)Cc1ccc(Cl)cc1>>O=C(Cc1ccc(Cl)cc1)Nn1nc(-c2ccc(F)cc2)c2ccccc2c1=O | US08629143B2_0571grants | 618b6b89fb591a837f24e41adb99ae4e5c85c55e2a0c0b5eaa397d69 | O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.[NH2:11][n:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1=[O:29] | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[NH:11][n:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[c:28]1=[O:29] | ([#7;a:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7;a:4]-[NH2;D1;+0:5]) | 33dc3a0971fed901e3a7789f4aa6bd433bb05fb3a059caddb35a1346 | 1 | 1 | null | 459 |
218,730 | 735,120 | 1,211,259 | C([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:25]=[CH:26][C:20]=3[N:19]=2)=[C:13]([Cl:40])[CH:12]=1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[Cl:17][C:15]1[CH:16]=[C:11]([CH:12]=[C:13]([Cl:40])[C:14]=1[C:18]1[NH:22][C:21]2[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH:25]=[CH:26][C:20]=2[N:19]=1)[O:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5] | null | US08222248B2_1392 | 2,012 | CC[O:29][P:27]([CH2:26][O:25][c:24]1[cH:23][c:21]([Cl:22])[c:20](-[c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:2](=[O:1])[NH:3][c:4]4[cH:5][cH:6][c:7]5[cH:8][cH:9][cH:10][cH:11][c:12]5[n:13]4)[cH:36][c:35]3[nH:34]2)[c:32]([Cl:33])[cH:31]1)(=[O:28])[O:30]CC.C[Si](C)(C)Br.ClCCl>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1)[c:14]1[cH:15][cH:16][c:17]2[n:18][c:19](-[c:20]3[c:21]([Cl:22])[cH:23][c:24]([O:25][CH2:26][P:27](=[O:28])([OH:29])[OH:30])[cH:31][c:32]3[Cl:33])[nH:34][c:35]2[cH:36]1 | 0.566816 | CCOP(=O)(COc1cc(Cl)c(-c2nc3ccc(C(=O)Nc4ccc5ccccc5n4)cc3[nH]2)c(Cl)c1)OCC.C[Si](C)(C)Br.ClCCl>>O=C(Nc1ccc2ccccc2n1)c1ccc2nc(-c3c(Cl)cc(OCP(=O)(O)O)cc3Cl)[nH]c2c1 | CCOP(=O)(COc1cc(Cl)c(-c2nc3ccc(C(=O)Nc4ccc5ccccc5n4)cc3[nH]2)c(Cl)c1)OCC.C[Si](C)(C)Br.ClCCl>>O=C(Nc1ccc2ccccc2n1)c1ccc2nc(-c3c(Cl)cc(OCP(=O)(O)O)cc3Cl)[nH]c2c1 | US08222248B2_1392grants | 570d576e28fbee0a81e3216a942b0c292243be40fe3afed71639ff8b | CC[O:29][P:27]([CH2:26][O:25][c:24]1[cH:23][c:21]([Cl:22])[c:20](-[c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:2](=[O:1])[NH:3][c:4]4[cH:5][cH:6][c:7]5[cH:8][cH:9][cH:10][cH:11][c:12]5[n:13]4)[cH:36][c:35]3[nH:34]2)[c:32]([Cl:33])[cH:31]1)(=[O:28])[O:30]CC.C[Si](C)(C)Br.ClCCl | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1)[c:14]1[cH:15][cH:16][c:17]2[n:18][c:19](-[c:20]3[c:21]([Cl:22])[cH:23][c:24]([O:25][CH2:26][P:27](=[O:28])([OH:29])[OH:30])[cH:31][c:32]3[Cl:33])[nH:34][c:35]2[cH:36]1 | ([OH;D1;+0:1]-[#15:2]-[OH;D1;+0:3])>>(C-C-[O;H0;D2;+0:1]-[#15:2]-[O;H0;D2;+0:3]-C-C) | b4595a08df6970ad8eb8dfa2ee3a90217a7c5435a1c378de56a3d36c | 1 | 1 | C[Si](C)(C)Br.ClCCl | 535 |
355,020 | 547,394 | null | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18](O)=[O:19])[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27]C)C.[CH3:31][N:32](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)CCCN>[CH3:24][N:26]([CH3:27])[CH2:29][CH2:30][CH2:31][NH:32][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([NH:14][C:12]2[CH:11]=[N:10][CH:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[N:13]=2)[CH:16]=1 | |f:2.3| | US20080039450A1_0791 | 2,008 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[cH:17][n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([OH:25])[cH:26][cH:27]3)[n:28]2)[cH:29]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[cH:17][n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([OH:25])[cH:26][cH:27]3)[n:28]2)[cH:29]1 | 0.862154 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[B-](F)(F)F.CN(C)CCCN.O=C(O)c1cccc(Nc2cncc(-c3ccc(O)cc3)n2)c1>>CN(C)CCCNC(=O)c1cccc(Nc2cncc(-c3ccc(O)cc3)n2)c1 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)CCCN.F[B-](F)(F)F.O=C(O)c1cccc(Nc2cncc(-c3ccc(O)cc3)n2)c1>>CN(C)CCCNC(=O)c1cccc(Nc2cncc(-c3ccc(O)cc3)n2)c1 | US20080039450A1_0791apps | fd4d11e324cf037a11a68b4661d858b4346ba0c06257dd28d9785449 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[cH:17][n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([OH:25])[cH:26][cH:27]3)[n:28]2)[cH:29]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH2:7] | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([NH:15][c:16]2[cH:17][n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([OH:25])[cH:26][cH:27]3)[n:28]2)[cH:29]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | CCN(CC)CC.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F | 334 |
3,389 | 17,797 | 23,021 | [H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:11]1)(=O)[CH3:8].O>O1CCCC1>[CH2:7]([N:10]1[CH2:15][CH2:14][O:13][CH:12]([CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:11]1)[CH3:8] | |f:0.1.2.3.4.5| | US04017621_ | 1,977 | C1CCOC1.O.O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH2:8][N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH2:8][N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1 | 0.817445 | C1CCOC1.CC(=O)N1CCOC(CN2c3ccccc3CCc3ccccc32)C1.O.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>CCN1CCOC(CN2c3ccccc3CCc3ccccc32)C1 | C1CCOC1.CC(=O)N1CCOC(CN2c3ccccc3CCc3ccccc32)C1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>CCN1CCOC(CN2c3ccccc3CCc3ccccc32)C1 | US04017621_grants | f9349558a272b1db214c22fedfb9607de4abca3b3ef581f8bc0b0c6b | C1CCOC1.O.O=[C:2]([CH3:1])[N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH2:8][N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][O:6][CH:7]([CH2:8][N:9]2[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]32)[CH2:24]1 | ([#7:2]-[CH2;D2;+0:1]-[C;D1;H3:3])>>(O=[C;H0;D3;+0:1](-[#7:2])-[C;D1;H3:3]) | 164bcd5926595fb14a6a9bdfa6263711f1e81657ce47f1a9ea439ccb | 1 | 1 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 112 |
307,490 | 1,000,056 | 1,691,072 | C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH2:15])=[CH:13][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:11]2)=[CH:6][C:5]=1[O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:15][C:14]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[C:5]([O:20][CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:6]=2)[N:11]=[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=1 | |f:1.2.3.4.5.6| | US09181242B2_0731 | 2,015 | C1CCOC1.CO[C:14]([c:13]1[cH:12][cH:11][c:10](-[n:9]2[c:7]([NH2:8])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:28]2)[cH:27][c:16]1[O:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:26]1)=[O:15].[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][OH:15])[c:16]([O:17][CH2:18][CH2:19][O:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:26]3)[cH:27]2)[n:28]1 | 0.402102 | C1CCOC1.COC(=O)c1ccc(-n2nc(C(C)(C)C)cc2N)cc1OCCOC1CCCCO1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>CC(C)(C)c1cc(N)n(-c2ccc(CO)c(OCCOC3CCCCO3)c2)n1 | C1CCOC1.COC(=O)c1ccc(-n2nc(C(C)(C)C)cc2N)cc1OCCOC1CCCCO1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>CC(C)(C)c1cc(N)n(-c2ccc(CO)c(OCCOC3CCCCO3)c2)n1 | US09181242B2_0731grants | e7406ccdd2dff49e9fae9edd91ea842bfeefa0b919c572d215540d19 | C1CCOC1.CO[C:14]([c:13]1[cH:12][cH:11][c:10](-[n:9]2[c:7]([NH2:8])[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:28]2)[cH:27][c:16]1[O:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:26]1)=[O:15].[Al+3].[H-].[H-].[H-].[H-].[Li+] | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH2:8])[n:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][OH:15])[c:16]([O:17][CH2:18][CH2:19][O:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][O:26]3)[cH:27]2)[n:28]1 | ([OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1)>>(C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1) | 9837206e9cbc012a1b67dbe24ef91db70782b4def0fddc7be5dd9197 | 1 | 1 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 444 |
421,791 | 1,774,483 | null | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[Cl:10][C:11]1[C:12]([C:18]([NH2:20])=[O:19])=[N:13][CH:14]=[CH:15][C:16]=1Cl.CC([O-])(C)C.[K+].O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:15]=[CH:14][N:13]=[C:12]([C:18]([NH2:20])=[O:19])[C:11]=2[Cl:10])=[C:4]([F:9])[CH:3]=1 | |f:2.3| | US20150299219A1_0453 | 2,015 | CC(C)(C)[O-].CN(C)C=O.Cl[c:8]1[cH:7][cH:6][n:5][c:4]([C:2]([NH2:1])=[O:3])[c:18]1[Cl:19].O.[K+].[OH:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][c:16]1[F:17]>>[NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][c:16]2[F:17])[c:18]1[Cl:19] | 0.993741 | CC(C)(C)[O-]~[K+].CN(C)C=O.NC(=O)c1nccc(Cl)c1Cl.Nc1ccc(O)c(F)c1.O>>NC(=O)c1nccc(Oc2ccc(N)cc2F)c1Cl | CC(C)(C)[O-].CN(C)C=O.NC(=O)c1nccc(Cl)c1Cl.Nc1ccc(O)c(F)c1.O.[K+]>>NC(=O)c1nccc(Oc2ccc(N)cc2F)c1Cl | US20150299219A1_0453apps | e8566a67397eb263cdbb1dbee36740347730122935a697677c45b0b2 | CC(C)(C)[O-].CN(C)C=O.Cl[c:8]1[cH:7][cH:6][n:5][c:4]([C:2]([NH2:1])=[O:3])[c:18]1[Cl:19].O.[K+].[OH:9][c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][c:16]1[F:17] | [NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][c:16]2[F:17])[c:18]1[Cl:19] | ([c:8]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([OH;D1;+0:7]-[c:8]) | 5c62785cb4ffa11a2d1342e51d253760ecdb159c6ae024e1469592cc | 1 | 1 | CC(C)(C)[O-].CN(C)C=O.O.[K+] | 351 |
4,665 | 23,982 | 33,525 | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1([CH3:23])[NH:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C(Cl)(Cl)Cl>N1C=CC=CC=1.O>[CH3:23][C:16]1([CH2:15][CH2:14][CH2:13][O:12][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[NH:20][C:19](=[O:21])[NH:18][C:17]1=[O:22] | null | US04061542_ | 1,977 | ClC(Cl)Cl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)(=[O:7])=[O:8].O.[OH:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:14])[NH:15][C:16](=[O:17])[NH:18][C:19]1=[O:20].c1ccncc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][C:13]2([CH3:14])[NH:15][C:16](=[O:17])[NH:18][C:19]2=[O:20])[cH:21][cH:22]1 | 0.501891 | CC1(CCCO)NC(=O)NC1=O.Cc1ccc(S(=O)(=O)Cl)cc1.ClC(Cl)Cl.O.c1ccncc1>>Cc1ccc(S(=O)(=O)OCCCC2(C)NC(=O)NC2=O)cc1 | CC1(CCCO)NC(=O)NC1=O.Cc1ccc(S(=O)(=O)Cl)cc1.ClC(Cl)Cl.O.c1ccncc1>>Cc1ccc(S(=O)(=O)OCCCC2(C)NC(=O)NC2=O)cc1 | US04061542_grants | cf89afba4bb27bf259e26c7853f5c3c211cfb5c0d16bae068b01bac3 | ClC(Cl)Cl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)(=[O:7])=[O:8].O.[OH:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:14])[NH:15][C:16](=[O:17])[NH:18][C:19]1=[O:20].c1ccncc1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][CH2:12][C:13]2([CH3:14])[NH:15][C:16](=[O:17])[NH:18][C:19]2=[O:20])[cH:21][cH:22]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[OH;D1;+0:6]) | 2a680215c1c69f116045ff1696194ac3ca890d5406b0abc3856bedc8 | 1 | 1 | ClC(Cl)Cl.O.c1ccncc1 | 197 |
177,094 | 616,673 | 1,022,398 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14]([OH:16])=O)[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=1[Cl:38]>>[Cl:38][C:31]1[CH:32]=[C:33]([C:34]#[N:35])[CH:36]=[CH:37][C:30]=1[NH:29][C:14](=[O:16])[CH:13]([N:12]1[C:11]2[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=2[N:9]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1 | null | US07816540B2_0546 | 2,010 | O[C:8](=[O:9])[CH:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[n:17]1[c:18](-[c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[n:26][c:27]2[cH:28][c:29]([F:30])[c:31]([F:32])[cH:33][c:34]12.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:35]([Cl:36])[cH:37]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[n:17]2[c:18](-[c:19]3[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]3)[n:26][c:27]3[cH:28][c:29]([F:30])[c:31]([F:32])[cH:33][c:34]23)[c:35]([Cl:36])[cH:37]1 | 0.792672 | N#Cc1ccc(N)c(Cl)c1.O=C(O)C(C1CCCCC1)n1c(-c2ccc(Cl)cc2)nc2cc(F)c(F)cc21>>N#Cc1ccc(NC(=O)C(C2CCCCC2)n2c(-c3ccc(Cl)cc3)nc3cc(F)c(F)cc32)c(Cl)c1 | N#Cc1ccc(N)c(Cl)c1.O=C(O)C(C1CCCCC1)n1c(-c2ccc(Cl)cc2)nc2cc(F)c(F)cc21>>N#Cc1ccc(NC(=O)C(C2CCCCC2)n2c(-c3ccc(Cl)cc3)nc3cc(F)c(F)cc32)c(Cl)c1 | US07816540B2_0546grants | a261683a4defbb40c10222a71e00ccd3d7df7fb535e082ce32111c32 | O[C:8](=[O:9])[CH:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[n:17]1[c:18](-[c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[n:26][c:27]2[cH:28][c:29]([F:30])[c:31]([F:32])[cH:33][c:34]12.[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:35]([Cl:36])[cH:37]1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH:10]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[n:17]2[c:18](-[c:19]3[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]3)[n:26][c:27]3[cH:28][c:29]([F:30])[c:31]([F:32])[cH:33][c:34]23)[c:35]([Cl:36])[cH:37]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 993a80a34f6acdc22e1630fbdadc440460d93877c75dd17e7db680f0 | 1 | 1 | null | 365 |
402,631 | 1,459,874 | null | [OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[C:13]=2[CH2:14][C:15]2[N:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][CH:16]=2)[CH:10]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([N:11]=[C:12]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=3)[C:13]=2[CH2:14][C:15]2[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][CH:16]=2)[CH:10]=1 | |f:0.1| | US20130331378A1_1131 | 2,013 | CO.C[O:16][C:14]([c:13]1[cH:12][cH:11][cH:10][c:9]([CH2:8][c:7]2[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][n:30]3[n:29][c:18]2-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[n:17]1)=[O:15].Cl.[K+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[n:17]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]3)[n:29][n:30]2[cH:31]1 | 0.208455 | CO.COC(=O)c1cccc(Cc2c(-c3ccc(C(F)(F)F)cc3)nn3cc(OC)ccc23)n1.Cl.[K+]~[OH-]>>COc1ccc2c(Cc3cccc(C(=O)O)n3)c(-c3ccc(C(F)(F)F)cc3)nn2c1 | CO.COC(=O)c1cccc(Cc2c(-c3ccc(C(F)(F)F)cc3)nn3cc(OC)ccc23)n1.Cl.[K+].[OH-]>>COc1ccc2c(Cc3cccc(C(=O)O)n3)c(-c3ccc(C(F)(F)F)cc3)nn2c1 | US20130331378A1_1131apps | ce75e88fceb7a4063383d2139b5f799d02acdfc6b0f0c0ed0982f099 | CO.C[O:16][C:14]([c:13]1[cH:12][cH:11][cH:10][c:9]([CH2:8][c:7]2[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][n:30]3[n:29][c:18]2-[c:19]2[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]2)[n:17]1)=[O:15].Cl.[K+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[n:17]3)[c:18](-[c:19]3[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]3)[n:29][n:30]2[cH:31]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b499e0b68ab8cc89df665c73ba592c6e17427fbd5b75a0a04b8fb5db | 1 | 1 | CO.Cl.[K+].[OH-] | 152 |
267,985 | 881,459 | 1,467,647 | C(NC1C=CC(C2C=C3C(CN([C@@H](C(C)C)C(O)=O)C3=O)=CC=2)=CC=1)(=O)C1C=CC=CC=1.[CH3:33][C:34]1[O:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:36][C:35]=1[C:45]([NH:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[CH:62]=[C:61]3[C:57]([CH2:58][N:59]([CH:64]4[CH2:69][CH2:68][CH2:67][CH:66]([C:70]([O:72]C)=[O:71])[CH2:65]4)[C:60]3=[O:63])=[CH:56][CH:55]=2)=[CH:50][CH:49]=1)=[O:46]>>[CH3:33][C:34]1[O:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:36][C:35]=1[C:45]([NH:47][C:48]1[CH:49]=[CH:50][C:51]([C:54]2[CH:62]=[C:61]3[C:57]([CH2:58][N:59]([CH:64]4[CH2:69][CH2:68][CH2:67][CH:66]([C:70]([OH:72])=[O:71])[CH2:65]4)[C:60]3=[O:63])=[CH:56][CH:55]=2)=[CH:52][CH:53]=1)=[O:46] | null | US08748426B2_2376 | 2,014 | CC(C)[C@@H](C(=O)O)N1Cc2ccc(-c3ccc(NC(=O)c4ccccc4)cc3)cc2C1=O.C[O:36][C:34]([CH:33]1[CH2:32][CH2:31][CH2:30][CH:29]([N:28]2[C:26](=[O:27])[c:24]3[c:23]([cH:22][cH:21][c:20](-[c:19]4[cH:18][cH:17][c:16]([NH:15][C:13]([c:12]5[c:2]([CH3:1])[o:3][c:4](-[c:5]6[cH:6][cH:7][cH:8][cH:9][cH:10]6)[n:11]5)=[O:14])[cH:40][cH:39]4)[cH:25]3)[CH2:38]2)[CH2:37]1)=[O:35]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[C:26](=[O:27])[N:28]([CH:29]2[CH2:30][CH2:31][CH2:32][CH:33]([C:34](=[O:35])[OH:36])[CH2:37]2)[CH2:38]3)[cH:39][cH:40]1 | 0.610113 | CC(C)[C@@H](C(=O)O)N1Cc2ccc(-c3ccc(NC(=O)c4ccccc4)cc3)cc2C1=O.COC(=O)C1CCCC(N2Cc3ccc(-c4ccc(NC(=O)c5nc(-c6ccccc6)oc5C)cc4)cc3C2=O)C1>>Cc1oc(-c2ccccc2)nc1C(=O)Nc1ccc(-c2ccc3c(c2)C(=O)N(C2CCCC(C(=O)O)C2)C3)cc1 | CC(C)[C@@H](C(=O)O)N1Cc2ccc(-c3ccc(NC(=O)c4ccccc4)cc3)cc2C1=O.COC(=O)C1CCCC(N2Cc3ccc(-c4ccc(NC(=O)c5nc(-c6ccccc6)oc5C)cc4)cc3C2=O)C1>>Cc1oc(-c2ccccc2)nc1C(=O)Nc1ccc(-c2ccc3c(c2)C(=O)N(C2CCCC(C(=O)O)C2)C3)cc1 | US08748426B2_2376grants | 0cf1cd870364dac7201e44ed6039905801b82b8565f401a01bb58018 | CC(C)[C@@H](C(=O)O)N1Cc2ccc(-c3ccc(NC(=O)c4ccccc4)cc3)cc2C1=O.C[O:36][C:34]([CH:33]1[CH2:32][CH2:31][CH2:30][CH:29]([N:28]2[C:26](=[O:27])[c:24]3[c:23]([cH:22][cH:21][c:20](-[c:19]4[cH:18][cH:17][c:16]([NH:15][C:13]([c:12]5[c:2]([CH3:1])[o:3][c:4](-[c:5]6[cH:6][cH:7][cH:8][cH:9][cH:10]6)[n:11]5)=[O:14])[cH:40][cH:39]4)[cH:25]3)[CH2:38]2)[CH2:37]1)=[O:35] | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[C:13](=[O:14])[NH:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[C:26](=[O:27])[N:28]([CH:29]2[CH2:30][CH2:31][CH2:32][CH:33]([C:34](=[O:35])[OH:36])[CH2:37]2)[CH2:38]3)[cH:39][cH:40]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CC(C)[C@@H](C(=O)O)N1Cc2ccc(-c3ccc(NC(=O)c4ccccc4)cc3)cc2C1=O | 88 |
259,394 | 857,420 | 1,426,790 | [NH2:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])=[O:27].O>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([CH2:12][OH:13])[C:3]([O:14][CH3:15])=[C:2]([NH:1][C:26](=[O:27])[O:28][CH2:29][C:30]([Cl:33])([Cl:32])[Cl:31])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10] | null | US08653304B2_0190 | 2,014 | C1CCOC1.CCN(C(C)C)C(C)C.Cl[C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23].O.[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[NH2:15]>>[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23] | 0.15989 | C1CCOC1.CCN(C(C)C)C(C)C.COc1c(N)cc(C(C)(C)C)cc1CO.O.O=C(Cl)OCC(Cl)(Cl)Cl>>COc1c(CO)cc(C(C)(C)C)cc1NC(=O)OCC(Cl)(Cl)Cl | C1CCOC1.CCN(C(C)C)C(C)C.COc1c(N)cc(C(C)(C)C)cc1CO.O.O=C(Cl)OCC(Cl)(Cl)Cl>>COc1c(CO)cc(C(C)(C)C)cc1NC(=O)OCC(Cl)(Cl)Cl | US08653304B2_0190grants | fb9758504591d189cd4748d3f0e51fc289e31ad5bbf939c7992d83eb | C1CCOC1.CCN(C(C)C)C(C)C.Cl[C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23].O.[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[NH2:15] | [CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23] | ([#8:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | e639aa1de09b5a6fe2985a0569a19edb84e942b2ee65974484d93573 | 1 | 1 | C1CCOC1.CCN(C(C)C)C(C)C.O | 102 |
328,782 | 24,962 | null | [S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:18]([CH:22]=1)[C:19](O)=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.[CH3:32][O:33][C:34](=[O:41])[C@H:35]([CH2:37][CH2:38][S:39][CH3:40])[NH2:36].Cl.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.ClCCl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:18]([CH:22]=1)[C:19]([NH:36][C@@H:35]([CH2:37][CH2:38][S:39][CH3:40])[C:34]([O:33][CH3:32])=[O:41])=[O:20])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1 | |f:3.4| | US20020058665A1_0503 | 2,002 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.Cl.ClCCl.O[C:11](=[O:12])[c:13]1[cH:14][c:15]([O:16][CH:17]([CH2:18][n:19]2[cH:20][cH:21][n:22][cH:23]2)[c:24]2[n:25][cH:26][cH:27][s:28]2)[cH:29][cH:30][c:31]1[CH2:32][CH2:33][c:34]1[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][S:8][CH3:9])[NH2:10]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][S:8][CH3:9])[NH:10][C:11](=[O:12])[c:13]1[cH:14][c:15]([O:16][CH:17]([CH2:18][n:19]2[cH:20][cH:21][n:22][cH:23]2)[c:24]2[n:25][cH:26][cH:27][s:28]2)[cH:29][cH:30][c:31]1[CH2:32][CH2:33][c:34]1[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]1 | 0.821355 | CCN=C=NCCCN(C)C~Cl.CN(C)c1ccncc1.COC(=O)[C@@H](N)CCSC.Cl.ClCCl.O=C(O)c1cc(OC(Cn2ccnc2)c2nccs2)ccc1CCc1ccc(F)cc1>>COC(=O)[C@H](CCSC)NC(=O)c1cc(OC(Cn2ccnc2)c2nccs2)ccc1CCc1ccc(F)cc1 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.COC(=O)[C@@H](N)CCSC.Cl.Cl.ClCCl.O=C(O)c1cc(OC(Cn2ccnc2)c2nccs2)ccc1CCc1ccc(F)cc1>>COC(=O)[C@H](CCSC)NC(=O)c1cc(OC(Cn2ccnc2)c2nccs2)ccc1CCc1ccc(F)cc1 | US20020058665A1_0503apps | 88633ad3b342555e39c5cfb70ed779ca2afee22acc4139ee6672e1c3 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.Cl.ClCCl.O[C:11](=[O:12])[c:13]1[cH:14][c:15]([O:16][CH:17]([CH2:18][n:19]2[cH:20][cH:21][n:22][cH:23]2)[c:24]2[n:25][cH:26][cH:27][s:28]2)[cH:29][cH:30][c:31]1[CH2:32][CH2:33][c:34]1[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][S:8][CH3:9])[NH2:10] | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][S:8][CH3:9])[NH:10][C:11](=[O:12])[c:13]1[cH:14][c:15]([O:16][CH:17]([CH2:18][n:19]2[cH:20][cH:21][n:22][cH:23]2)[c:24]2[n:25][cH:26][cH:27][s:28]2)[cH:29][cH:30][c:31]1[CH2:32][CH2:33][c:34]1[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]1 | ([C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH2;D1;+0:9]) | 8eba64e9b8380cd5216a5675f278670915caad6c889cde2b52fe0db2 | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.Cl.ClCCl | 652 |
270,998 | 889,803 | 1,483,404 | [BH4-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH:22]=[O:23])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][OH:23])[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5] | |f:0.1,3.4| | US08778963B2_1513 | 2,014 | CCO.O=C([O-])O.[BH4-].[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH:20]=[O:21].[Na+].[Na+]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][OH:21] | 0.971142 | CCCc1nc2cnc3ccccc3c2n1CCCC=O.CCO.O=C([O-])O~[Na+].[BH4-]~[Na+]>>CCCc1nc2cnc3ccccc3c2n1CCCCO | CCCc1nc2cnc3ccccc3c2n1CCCC=O.CCO.O=C([O-])O.[BH4-].[Na+].[Na+]>>CCCc1nc2cnc3ccccc3c2n1CCCCO | US08778963B2_1513grants | 31b2a50e05710101d358a657dd8412472a3a23bb7c8bd9746c28175b | CCO.O=C([O-])O.[BH4-].[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH:20]=[O:21].[Na+].[Na+] | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][CH2:18][CH2:19][CH2:20][OH:21] | ([C:1]-[CH2;D2;+0:2]-[OH;D1;+0:3])>>([C:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3]) | 1dd4dec9f0a6b0036351341bbee3ca89ca2d60857539d67a1cf43010 | 1 | 1 | CCO.O=C([O-])O.[BH4-].[Na+].[Na+] | 223 |
202,311 | 689,065 | 1,136,664 | Cl.Cl.[OH:3][C@@H:4]1[CH2:11][N:10]([CH2:12][CH2:13][CH2:14][N:15]2[C:21](=[O:22])[CH2:20][CH2:19][NH:18][C@H:17]([CH3:23])[CH2:16]2)[CH2:9][CH2:8][C:5]21[CH2:7][CH2:6]2.[CH3:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]>>[CH3:24][C:25]1[CH:26]=[C:27]([NH:32][C:33]([N:18]2[CH2:19][CH2:20][C:21](=[O:22])[N:15]([CH2:14][CH2:13][CH2:12][N:10]3[CH2:9][CH2:8][C:5]4([CH2:6][CH2:7]4)[C@H:4]([OH:3])[CH2:11]3)[CH2:16][C@H:17]2[CH3:23])=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31] | |f:0.1.2| | US08071586B2_0581 | 2,011 | Cl.Cl.[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:30][c:31]1[CH3:32].[NH:9]1[CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][C:21]3([CH2:22][CH2:23]3)[C@H:24]([OH:25])[CH2:26]2)[CH2:27][C@H:28]1[CH3:29]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][C:21]4([CH2:22][CH2:23]4)[C@H:24]([OH:25])[CH2:26]3)[CH2:27][C@H:28]2[CH3:29])[cH:30][c:31]1[CH3:32] | 0.899984 | C[C@@H]1CN(CCCN2CCC3(CC3)[C@H](O)C2)C(=O)CCN1~Cl~Cl.Cc1ccc(N=C=O)cc1C>>Cc1ccc(NC(=O)N2CCC(=O)N(CCCN3CCC4(CC4)[C@H](O)C3)C[C@H]2C)cc1C | C[C@@H]1CN(CCCN2CCC3(CC3)[C@H](O)C2)C(=O)CCN1.Cc1ccc(N=C=O)cc1C.Cl.Cl>>Cc1ccc(NC(=O)N2CCC(=O)N(CCCN3CCC4(CC4)[C@H](O)C3)C[C@H]2C)cc1C | US08071586B2_0581grants | 1ed7e31fb6e4bcd8c5fd758ac70eb3d0eea30d2639b5a0d2bfaf7990 | Cl.Cl.[CH3:1][c:2]1[cH:3][cH:4][c:5]([N:6]=[C:7]=[O:8])[cH:30][c:31]1[CH3:32].[NH:9]1[CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][C:21]3([CH2:22][CH2:23]3)[C@H:24]([OH:25])[CH2:26]2)[CH2:27][C@H:28]1[CH3:29] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[N:9]2[CH2:10][CH2:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][C:21]4([CH2:22][CH2:23]4)[C@H:24]([OH:25])[CH2:26]3)[CH2:27][C@H:28]2[CH3:29])[cH:30][c:31]1[CH3:32] | ([C:1]-[N;H0;D3;+0:2](-[C:3])-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7])>>([C:1]-[NH;D2;+0:2]-[C:3]).([O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7]) | 09f63f034bbf4b29cbba07c3cfc12d8be3ce5a732a0a513d3a933b0e | 1 | 1 | Cl.Cl | 323 |
161,145 | 569,589 | 950,050 | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH2:14][OH:15])[NH:12][N:13]=2)=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[NH:12][N:13]=2)=[CH:7][CH:8]=1 | |f:1.2.3| | US07645756B2_0556 | 2,010 | ClC(Cl)Cl.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[nH:12][n:13]2)[cH:14][cH:15]1.[Mn+4].[O-2].[O-2]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[nH:12][n:13]2)[cH:14][cH:15]1 | 0.968869 | COc1ccc(-c2cc(CO)[nH]n2)cc1.ClC(Cl)Cl.[Mn+4]~[O-2]~[O-2]>>COc1ccc(-c2cc(C=O)[nH]n2)cc1 | COc1ccc(-c2cc(CO)[nH]n2)cc1.ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>>COc1ccc(-c2cc(C=O)[nH]n2)cc1 | US07645756B2_0556grants | 0d2f27f723ba8b8edc6c02e2b28579a8e222195bc2e2720d43d34952 | ClC(Cl)Cl.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[nH:12][n:13]2)[cH:14][cH:15]1.[Mn+4].[O-2].[O-2] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[nH:12][n:13]2)[cH:14][cH:15]1 | ([#7;a:1]:[#7;a:2]:[c:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])>>([#7;a:1]:[#7;a:2]:[c:3]-[CH2;D2;+0:4]-[OH;D1;+0:5]) | 7c58b87004a2cad9f9d9431e7f6cfec26953050608f288528b6ea213 | 1 | 1 | ClC(Cl)Cl.[Mn+4].[O-2].[O-2] | 573 |
200,064 | 682,976 | 1,126,869 | [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=2)[CH3:18])[C:13]([CH3:33])=[N:12]1.[OH-].[Na+].Cl>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15](=[O:16])[C:14](=[C:17]([NH:19][NH:20][C:21](=[O:32])[C:22]2[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[CH:26][CH:27]=2)[CH3:18])[C:13]([CH3:33])=[N:12]1 | |f:1.2| | US08053453B2_0293 | 2,011 | CO.C[O:30][C:28]([c:27]1[cH:26][cH:25][c:24]([C:22]([NH:21][NH:20][C:18](=[C:17]2[C:2]([CH3:1])=[N:3][N:4]([c:5]3[cH:6][cH:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[n:14]3)[C:15]2=[O:16])[CH3:19])=[O:23])[cH:32][cH:31]1)=[O:29].Cl.[Na+].[OH-]>>[CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[n:14]2)[C:15](=[O:16])[C:17]1=[C:18]([CH3:19])[NH:20][NH:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1 | 0.892085 | CO.COC(=O)c1ccc(C(=O)NNC(C)=C2C(=O)N(c3ccc4ccccc4n3)N=C2C)cc1.Cl.[Na+]~[OH-]>>CC1=NN(c2ccc3ccccc3n2)C(=O)C1=C(C)NNC(=O)c1ccc(C(=O)O)cc1 | CO.COC(=O)c1ccc(C(=O)NNC(C)=C2C(=O)N(c3ccc4ccccc4n3)N=C2C)cc1.Cl.[Na+].[OH-]>>CC1=NN(c2ccc3ccccc3n2)C(=O)C1=C(C)NNC(=O)c1ccc(C(=O)O)cc1 | US08053453B2_0293grants | 5328fd924fc9f26a6920421ace03a2054da0bed438e69c9be976a8f8 | CO.C[O:30][C:28]([c:27]1[cH:26][cH:25][c:24]([C:22]([NH:21][NH:20][C:18](=[C:17]2[C:2]([CH3:1])=[N:3][N:4]([c:5]3[cH:6][cH:7][c:8]4[cH:9][cH:10][cH:11][cH:12][c:13]4[n:14]3)[C:15]2=[O:16])[CH3:19])=[O:23])[cH:32][cH:31]1)=[O:29].Cl.[Na+].[OH-] | [CH3:1][C:2]1=[N:3][N:4]([c:5]2[cH:6][cH:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[n:14]2)[C:15](=[O:16])[C:17]1=[C:18]([CH3:19])[NH:20][NH:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | CO.Cl.[Na+].[OH-] | 247 |
286,907 | 936,547 | 1,570,989 | C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1.[O:26]1[CH2:29][C:28](=O)[CH2:27]1>ClCCCl>[O:26]1[CH2:29][CH:28]([N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH2:27]1 | |f:0.1| | US08940736B2_1650 | 2,015 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCCl.O=[C:6]1[CH2:7][O:8][CH2:9]1.[Na+].[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:10][CH2:11]1>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH:6]2[CH2:7][O:8][CH2:9]2)[CH2:10][CH2:11]1 | 0.81896 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].ClCCCl.O=C1COC1.OC1CCNCC1>>OC1CCN(C2COC2)CC1 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCCl.O=C1COC1.OC1CCNCC1.[Na+]>>OC1CCN(C2COC2)CC1 | US08940736B2_1650grants | 169290d097d0469796863c1053faf4ae802b7f7bbb090cb44956126f | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCCl.O=[C:6]1[CH2:7][O:8][CH2:9]1.[Na+].[OH:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:10][CH2:11]1 | [OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH:6]2[CH2:7][O:8][CH2:9]2)[CH2:10][CH2:11]1 | ([C:5]-[N;H0;D3;+0:6](-[C:7])-[CH;D3;+0:1]1-[C:2]-[#8:3]-[C:4]-1)>>(O=[C;H0;D3;+0:1]1-[C:2]-[#8:3]-[C:4]-1).([C:5]-[NH;D2;+0:6]-[C:7]) | 422db9d9d56b3bc5c1561e0719ce261b3c5ca71e90e9d38c3c13bbf0 | 1 | 1 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCCl.[Na+] | 983 |
411,642 | 1,657,455 | null | [H-].[Na+].F[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][OH:20]>CN(C=O)C.CCOC(C)=O>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][O:20][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1 | |f:0.1| | US20150057298A1_0494 | 2,015 | CCOC(C)=O.CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:17][cH:16]1.[H-].[Na+].[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[cH:16][cH:17]1 | 0.95031 | CCOC(C)=O.CN(C)C=O.O=Cc1ccc(F)cc1.OCc1ccccc1F.[H-]~[Na+]>>O=Cc1ccc(OCc2ccccc2F)cc1 | CCOC(C)=O.CN(C)C=O.O=Cc1ccc(F)cc1.OCc1ccccc1F.[H-].[Na+]>>O=Cc1ccc(OCc2ccccc2F)cc1 | US20150057298A1_0494apps | d2f2a988f2be34a24c42b77a0bcb3fd6502c29ed6d37efe6d78fc1a8 | CCOC(C)=O.CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:17][cH:16]1.[H-].[Na+].[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15] | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[cH:16][cH:17]1 | ([C:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 5e910f78c09147f95443e74bed5b26e7557d68f73dba61bcb03d2b4e | 1 | 1 | CCOC(C)=O.CN(C)C=O.[H-].[Na+] | 485 |
198,086 | 678,094 | 1,119,572 | [Cl:1][S:2]([OH:5])(=O)=[O:3].[Br:6][C:7]1[CH:8]=[C:9]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:10]=[CH:11][C:12]=1[OH:13]>>[Br:6][C:7]1[C:12]([OH:13])=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=[C:9]([CH:14]2[C:23]3[C:22](=[O:24])[CH2:21][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:19][C:18]=3[NH:17][C:16]([CH3:28])=[C:15]2[C:29]#[N:30])[CH:8]=1 | null | US08034945B2_0350 | 2,011 | O[S:25](=[O:26])(=[O:27])[Cl:28].[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][C:6](=[O:7])[C:8]2=[C:9]([CH2:10]1)[NH:11][C:12]([CH3:13])=[C:14]([C:15]#[N:16])[CH:17]2[c:18]1[cH:19][c:20]([Br:21])[c:22]([OH:23])[cH:24][cH:29]1>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][C:6](=[O:7])[C:8]2=[C:9]([CH2:10]1)[NH:11][C:12]([CH3:13])=[C:14]([C:15]#[N:16])[CH:17]2[c:18]1[cH:19][c:20]([Br:21])[c:22]([OH:23])[c:24]([S:25](=[O:26])(=[O:27])[Cl:28])[cH:29]1 | 0.240159 | CCCC1CC(=O)C2=C(C1)NC(C)=C(C#N)C2c1ccc(O)c(Br)c1.O=S(=O)(O)Cl>>CCCC1CC(=O)C2=C(C1)NC(C)=C(C#N)C2c1cc(Br)c(O)c(S(=O)(=O)Cl)c1 | CCCC1CC(=O)C2=C(C1)NC(C)=C(C#N)C2c1ccc(O)c(Br)c1.O=S(=O)(O)Cl>>CCCC1CC(=O)C2=C(C1)NC(C)=C(C#N)C2c1cc(Br)c(O)c(S(=O)(=O)Cl)c1 | US08034945B2_0350grants | 7907934623751c3b6c42514ca2b975fecb13780ec6b7adf426ca45a3 | O[S:25](=[O:26])(=[O:27])[Cl:28].[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][C:6](=[O:7])[C:8]2=[C:9]([CH2:10]1)[NH:11][C:12]([CH3:13])=[C:14]([C:15]#[N:16])[CH:17]2[c:18]1[cH:19][c:20]([Br:21])[c:22]([OH:23])[cH:24][cH:29]1 | [CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][C:6](=[O:7])[C:8]2=[C:9]([CH2:10]1)[NH:11][C:12]([CH3:13])=[C:14]([C:15]#[N:16])[CH:17]2[c:18]1[cH:19][c:20]([Br:21])[c:22]([OH:23])[c:24]([S:25](=[O:26])(=[O:27])[Cl:28])[cH:29]1 | ([Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:6](:[c:5]):[c:7])>>(O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([c:5]:[cH;D2;+0:6]:[c:7]) | 17d1e9f83f0d5f9a5150376a589031278906299deee311524cf33e00 | 1 | 1 | null | 357 |
252,204 | 836,355 | 1,387,513 | [S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:9]1)=[O:7].Cl>CO.O1CCOCC1>[NH2:13][C@H:10]1[CH2:11][CH2:12][N:8]([C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)=[O:7])[CH2:9]1 | null | US08575363B2_0478 | 2,013 | C1COCCO1.CC(C)(C)OC(=O)[NH:1][C@H:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][s:12]2)[CH2:13]1.CO.Cl>>[NH2:1][C@H:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][s:12]2)[CH2:13]1 | 0.997678 | C1COCCO1.CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)c2nccs2)C1.CO.Cl>>N[C@H]1CCN(C(=O)c2nccs2)C1 | C1COCCO1.CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)c2nccs2)C1.CO.Cl>>N[C@H]1CCN(C(=O)c2nccs2)C1 | US08575363B2_0478grants | badc03c318f19bfb81bbff38ac287dd5b38642c0dd810093b80ec0ea | C1COCCO1.CC(C)(C)OC(=O)[NH:1][C@H:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][s:12]2)[CH2:13]1.CO.Cl | [NH2:1][C@H:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][s:12]2)[CH2:13]1 | ([C:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]) | 6c83f45f485301792011c63e6835be21ece3be24f5b32a6e45acc5be | 1 | 1 | C1COCCO1.CO.Cl | 538 |
297,603 | 968,488 | 1,630,446 | Cl.[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8].[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:2][O:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:17]=[CH:16][C:15]2[C:11](=[CH:12][N:13]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:30][CH:31]=4)[CH2:23][CH2:24]3)[N:14]=2)[C:10]=1[CH3:25])=[O:8] | |f:0.1| | US09062041B2_0500 | 2,015 | Cc1ccccc1.Cl.Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1.[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]2[n:12][n:13]([CH2:14][CH:15]3[CH2:16][CH2:17][NH:18][CH2:32][CH2:33]3)[cH:34][c:35]2[c:36]1[CH3:37].c1ccncc1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]2[n:12][n:13]([CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]4)[CH2:32][CH2:33]3)[cH:34][c:35]2[c:36]1[CH3:37] | 0.222349 | COCCNC(=O)c1ccc2nn(CC3CCNCC3)cc2c1C~Cl.Cc1ccccc1.O=C(Cl)c1ccc(OC(F)(F)F)cc1.c1ccncc1>>COCCNC(=O)c1ccc2nn(CC3CCN(C(=O)c4ccc(OC(F)(F)F)cc4)CC3)cc2c1C | COCCNC(=O)c1ccc2nn(CC3CCNCC3)cc2c1C.Cc1ccccc1.Cl.O=C(Cl)c1ccc(OC(F)(F)F)cc1.c1ccncc1>>COCCNC(=O)c1ccc2nn(CC3CCN(C(=O)c4ccc(OC(F)(F)F)cc4)CC3)cc2c1C | US09062041B2_0500grants | 7feb76b79fdbde4ed1c26c6d08628f0f7c053275314b89bf6b2b5b4c | Cc1ccccc1.Cl.Cl[C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1.[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]2[n:12][n:13]([CH2:14][CH:15]3[CH2:16][CH2:17][NH:18][CH2:32][CH2:33]3)[cH:34][c:35]2[c:36]1[CH3:37].c1ccncc1 | [CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]2[n:12][n:13]([CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:19](=[O:20])[c:21]4[cH:22][cH:23][c:24]([O:25][C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]4)[CH2:32][CH2:33]3)[cH:34][c:35]2[c:36]1[CH3:37] | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 8e776da45ba18fd7625e94abe947f9adcda1a9454a884e9be672df24 | 1 | 1 | Cc1ccccc1.Cl.c1ccncc1 | 201 |
4,724 | 24,427 | 34,300 | [BH4-].[Na+].[CH:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CO>[CH:3]1([C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:17])[CH3:16])=[CH:13][CH:14]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1 | |f:0.1| | US04062973_ | 1,977 | CO.[BH4-].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1.[Na+]>>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | 0.907256 | CC(=O)c1ccc(C2CCCCC2)cc1.CO.[BH4-]~[Na+]>>CC(O)c1ccc(C2CCCCC2)cc1 | CC(=O)c1ccc(C2CCCCC2)cc1.CO.[BH4-].[Na+]>>CC(O)c1ccc(C2CCCCC2)cc1 | US04062973_grants | a3dd2206568bc7c4854e9fbe6d64868307b134cc60f6696add81a47f | CO.[BH4-].[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1.[Na+] | [CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | ([C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4])>>([C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]) | e79b9f0e956cb38254670cbba4f53d0c22148efe9b15465e130440fe | 1 | 1 | CO.[BH4-].[Na+] | 24 |
6,287 | 32,496 | 49,143 | [Cl:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH3:21])=[CH:14][CH:13]=2)[C:8]([O:10]C)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH:20]([O:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH3:21])=[CH:16][CH:17]=2)[C:8]([OH:10])=[O:9])=[CH:30][CH:31]=1 | |f:1.2| | US04125732_ | 1,978 | C[O:20][C:18]([CH:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][CH:2]([CH3:1])[O:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[cH:22][cH:21]1)[O:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)=[O:19].[K+].[OH-]>>[CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[C:18](=[O:19])[OH:20])[cH:21][cH:22]1)[O:23][c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1 | 0.833932 | COC(=O)C(Oc1ccc(Cl)cc1)c1ccc(OCC(C)Oc2ccc(Cl)cc2)cc1.[K+]~[OH-]>>CC(COc1ccc(C(Oc2ccc(Cl)cc2)C(=O)O)cc1)Oc1ccc(Cl)cc1 | COC(=O)C(Oc1ccc(Cl)cc1)c1ccc(OCC(C)Oc2ccc(Cl)cc2)cc1.[K+].[OH-]>>CC(COc1ccc(C(Oc2ccc(Cl)cc2)C(=O)O)cc1)Oc1ccc(Cl)cc1 | US04125732_grants | 2b4888408dae1f5a2a1531eced41b4cbe0fcf48b0739fe92372705b7 | C[O:20][C:18]([CH:9]([c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][CH:2]([CH3:1])[O:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[cH:22][cH:21]1)[O:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)=[O:19].[K+].[OH-] | [CH3:1][CH:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([O:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[C:18](=[O:19])[OH:20])[cH:21][cH:22]1)[O:23][c:24]1[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | [K+].[OH-] | 88 |
56,046 | 240,427 | 404,148 | O1CCCC1.[CH2:6]([OH:9])[CH2:7][OH:8].[H-].[Na+].[Cl:12][C:13]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:17](Cl)[N:16]=[CH:15][N:14]=1>C(O)(=O)C>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([O:8][CH2:7][CH2:6][OH:9])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1 | |f:2.3| | US05739333_ | 1,998 | C1CCOC1.CC(=O)O.Cl[c:12]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:7]([Cl:8])[n:9][cH:10][n:11]1.[H-].[Na+].[OH:13][CH2:14][CH2:15][OH:16]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]1 | 0.489631 | C1CCOC1.CC(=O)O.Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.OCCO.[H-]~[Na+]>>Cc1ccc(-c2c(Cl)ncnc2OCCO)cc1 | C1CCOC1.CC(=O)O.Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.OCCO.[H-].[Na+]>>Cc1ccc(-c2c(Cl)ncnc2OCCO)cc1 | US05739333_grants | bc195c0f8aec496ec45025509816c7807b3679ca5c6624dd371386fd | C1CCOC1.CC(=O)O.Cl[c:12]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)[c:7]([Cl:8])[n:9][cH:10][n:11]1.[H-].[Na+].[OH:13][CH2:14][CH2:15][OH:16] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]([Cl:8])[n:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]1 | ([C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C:7]-[OH;D1;+0:8]) | 5143b901619ce0acc66a8a625982dda04978c2b35cb026eacddddf7e | 1 | 1 | C1CCOC1.CC(=O)O.[H-].[Na+] | 653 |
380,899 | 944,098 | null | [Br:1][C:2]1[C:10]([CH2:11]Br)=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[CH3:13][C:14]1[NH:18][N:17]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]=1[N+:24]([O-:26])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CC#N.O>[Br:1][C:2]1[C:10]([CH2:11][N:18]2[C:14]([CH3:13])=[C:15]([N+:24]([O-:26])=[O:25])[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:17]2)=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1 | |f:2.3.4,5.6| | US20100240656A1_0310 | 2,010 | Br[CH2:9][c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Br:16])[O:17][CH2:18][O:19]2.CC#N.O.O=C([O-])O.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:20]([CH3:21])[c:22]1[N+:23](=[O:24])[O-:25].[Cs+].[Cs+].[Na+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][n:8]([CH2:9][c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[Br:16])[O:17][CH2:18][O:19]3)[c:20]([CH3:21])[c:22]1[N+:23](=[O:24])[O-:25] | 0.941662 | BrCc1cc2c(cc1Br)OCO2.CC#N.CCOC(=O)c1n[nH]c(C)c1[N+](=O)[O-].O.O=C([O-])O~[Na+].O=C([O-])[O-]~[Cs+]~[Cs+]>>CCOC(=O)c1nn(Cc2cc3c(cc2Br)OCO3)c(C)c1[N+](=O)[O-] | BrCc1cc2c(cc1Br)OCO2.CC#N.CCOC(=O)c1n[nH]c(C)c1[N+](=O)[O-].O.O=C([O-])O.O=C([O-])[O-].[Cs+].[Cs+].[Na+]>>CCOC(=O)c1nn(Cc2cc3c(cc2Br)OCO3)c(C)c1[N+](=O)[O-] | US20100240656A1_0310apps | 28ca57e0c23d10ebad6759b58cfa460abb68f1f99e0b43366a5ceefc | Br[CH2:9][c:10]1[cH:11][c:12]2[c:13]([cH:14][c:15]1[Br:16])[O:17][CH2:18][O:19]2.CC#N.O.O=C([O-])O.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][nH:8][c:20]([CH3:21])[c:22]1[N+:23](=[O:24])[O-:25].[Cs+].[Cs+].[Na+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][n:8]([CH2:9][c:10]2[cH:11][c:12]3[c:13]([cH:14][c:15]2[Br:16])[O:17][CH2:18][O:19]3)[c:20]([CH3:21])[c:22]1[N+:23](=[O:24])[O-:25] | ([#7;a:3]:[n;H0;D3;+0:4](:[c:5])-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([#7;a:3]:[nH;D2;+0:4]:[c:5]) | 3ab43d60fd600ef323cdaa2e5c4d5c6d49126c83a9eba583fd0279de | 1 | 1 | CC#N.O.O=C([O-])O.O=C([O-])[O-].[Cs+].[Cs+].[Na+] | 635 |
163,413 | 575,970 | 959,539 | [F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([OH:16])=O)=[CH:5][CH:4]=1.[CH2:19]([CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:14]([C:10]1[CH:11]=[N:12][O:13][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:17])=[CH:8][CH:7]=1)=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1 | null | US07666888B2_0442 | 2,010 | O[C:2](=[O:1])[c:3]1[cH:4][n:5][o:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.[NH:18]1[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[O:1]=[C:2]([c:3]1[cH:4][n:5][o:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1)[N:18]1[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1 | 0.172975 | O=C(O)c1cnoc1-c1ccc(C(F)(F)F)cc1.c1ccc(CC2CCCN2)cc1>>O=C(c1cnoc1-c1ccc(C(F)(F)F)cc1)N1CCCC1Cc1ccccc1 | O=C(O)c1cnoc1-c1ccc(C(F)(F)F)cc1.c1ccc(CC2CCCN2)cc1>>O=C(c1cnoc1-c1ccc(C(F)(F)F)cc1)N1CCCC1Cc1ccccc1 | US07666888B2_0442grants | 7680766a6c083c33d4d61075da240564fdb39c0251810ab110cb7951 | O[C:2](=[O:1])[c:3]1[cH:4][n:5][o:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.[NH:18]1[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1 | [O:1]=[C:2]([c:3]1[cH:4][n:5][o:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1)[N:18]1[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1 | ([C:8]-[N;H0;D3;+0:9](-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#8;a:6]:[c:7]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#8;a:6]:[c:7]:1).([C:8]-[NH;D2;+0:9]-[C:10]) | 4f1c577a6b6633ffc5f7dbc2b08084fd291de57064137ba88d19e7f6 | 1 | 1 | null | 975 |
125,878 | 463,750 | 785,229 | [C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[Cl:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:7][C:6]=1[Cl:12])([CH3:4])([CH3:2])[CH3:3] | |f:1.2.3| | US07214824B2_0380 | 2,007 | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CC(C)=O.O=C([O-])[O-].[K+].[K+].[OH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([Cl:19])[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([Cl:19])[cH:20]1 | 0.236474 | CC(C)(C)OC(=O)CBr.CC(C)(C)c1ccc(O)cc1Cl.CC(C)=O.O=C([O-])[O-]~[K+]~[K+]>>CC(C)(C)OC(=O)COc1ccc(C(C)(C)C)c(Cl)c1 | CC(C)(C)OC(=O)CBr.CC(C)(C)c1ccc(O)cc1Cl.CC(C)=O.O=C([O-])[O-].[K+].[K+]>>CC(C)(C)OC(=O)COc1ccc(C(C)(C)C)c(Cl)c1 | US07214824B2_0380grants | f3e5b8e464000727739b59db5decd67deb6d3591a180e9a00d5d29e7 | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CC(C)=O.O=C([O-])[O-].[K+].[K+].[OH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([Cl:19])[cH:20]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([Cl:19])[cH:20]1 | ([C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10])>>(Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]).([OH;D1;+0:9]-[c:10]) | 4322b142e677dd0d75016cf2b72a9e7fd4bd79cf479d3a1b1c3f9019 | 1 | 1 | CC(C)=O.O=C([O-])[O-].[K+].[K+] | 393 |
127,781 | 469,142 | 794,376 | C[O:2][C:3]([C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:18])[CH:15]=3)[N:10]([CH3:19])[C:9]=2[C:8]([O:20][CH3:21])=[CH:7][CH:6]=1)=[O:4]>CO.[OH-].[Na+]>[Cl:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:19])[C:9]1[C:8]([O:20][CH3:21])=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:17]2=1 | |f:2.3| | US07238725B2_1233 | 2,007 | CO.C[O:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]2[c:10]1[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[n:18]2[CH3:19])=[O:8].[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]([CH3:19])[c:20]12 | 0.953547 | CO.COC(=O)c1ccc(OC)c2c1c1cc(Cl)ccc1n2C.[Na+]~[OH-]>>COc1ccc(C(=O)O)c2c3cc(Cl)ccc3n(C)c12 | CO.COC(=O)c1ccc(OC)c2c1c1cc(Cl)ccc1n2C.[Na+].[OH-]>>COc1ccc(C(=O)O)c2c3cc(Cl)ccc3n(C)c12 | US07238725B2_1233grants | 5c308a5dc0acb930fe90bf0b875ad0190829e8276170a569febff598 | CO.C[O:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]2[c:10]1[c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1[n:18]2[CH3:19])=[O:8].[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]3[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3[n:18]([CH3:19])[c:20]12 | ([C;D1;H3:9]-[#8:8]-[c:7]1:[c:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:11]:[c:10]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[#8:8]-[C;D1;H3:9]):[c:10]:[c:11]:1) | 1f30ff7184a936c3d6949b8da68f661883b9aca9556111a18280f156 | 1 | 1 | CO.[Na+].[OH-] | 222 |
90,784 | 357,079 | 608,787 | [OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2[N+:19]([O-])=O)[CH2:4][CH2:3]1>[Pd].CO.O1CCOCC1>[NH2:19][C:10]1[CH:11]=[C:12]([C:15]([F:16])([F:17])[F:18])[CH:13]=[CH:14][C:9]=1[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([OH:1])[CH2:3][CH2:4]1 | null | US06582351B1_ | 2,003 | C1COCCO1.CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([OH:17])[CH2:18][CH2:19]1.[Pd]>>[NH2:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([OH:17])[CH2:18][CH2:19]1 | 0.238271 | C1COCCO1.CO.O=[N+]([O-])c1cc(C(F)(F)F)ccc1N[C@@H]1CC[C@@H](O)CC1.[Pd]>>Nc1cc(C(F)(F)F)ccc1N[C@@H]1CC[C@@H](O)CC1 | C1COCCO1.CO.O=[N+]([O-])c1cc(C(F)(F)F)ccc1N[C@@H]1CC[C@@H](O)CC1.[Pd]>>Nc1cc(C(F)(F)F)ccc1N[C@@H]1CC[C@@H](O)CC1 | US06582351B1_grants | 0a64eff7844796976fda7268dd4f270b5679dd36c14f6fef4a55f3d1 | C1COCCO1.CO.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([OH:17])[CH2:18][CH2:19]1.[Pd] | [NH2:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][cH:10][c:11]1[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([OH:17])[CH2:18][CH2:19]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | C1COCCO1.CO.[Pd] | 1 |
375,847 | 860,824 | null | [CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:10]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[C:34](O)=[O:35].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]([CH2:20][N:21]([CH:22]([CH3:24])[CH3:23])[C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:39]([O:40][CH3:41])=[C:31]([O:30][CH2:29][CH2:28][CH2:27][O:26][CH3:25])[CH:32]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US20100087427A1_0713 | 2,010 | CCN(CC)CC.ClCCl.O=C1OCCN1P(=O)(Cl)N1CCOC1=O.O[C:10]([c:9]1[cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]([O:39][CH3:40])[cH:37][cH:36]1)=[O:11].[NH:12]([CH2:13][C@H:14]1[CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][C@H:25]1[CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH:33]([CH3:34])[CH3:35]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][C@H:14]2[CH2:15][N:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][C@H:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH:33]([CH3:34])[CH3:35])[cH:36][cH:37][c:38]1[O:39][CH3:40] | 0.512304 | CC(C)NC[C@H]1CN(Cc2ccccc2)C[C@H]1Cc1ccccc1.CCN(CC)CC.COCCCOc1cc(C(=O)O)ccc1OC.ClCCl.O=C1OCCN1P(=O)(Cl)N1CCOC1=O>>COCCCOc1cc(C(=O)N(C[C@H]2CN(Cc3ccccc3)C[C@H]2Cc2ccccc2)C(C)C)ccc1OC | CC(C)NC[C@H]1CN(Cc2ccccc2)C[C@H]1Cc1ccccc1.CCN(CC)CC.COCCCOc1cc(C(=O)O)ccc1OC.ClCCl.O=C1OCCN1P(=O)(Cl)N1CCOC1=O>>COCCCOc1cc(C(=O)N(C[C@H]2CN(Cc3ccccc3)C[C@H]2Cc2ccccc2)C(C)C)ccc1OC | US20100087427A1_0713apps | abd9529b92d90a20678842195a0ca934ecb518b8b1bc95d0537d39e4 | CCN(CC)CC.ClCCl.O=C1OCCN1P(=O)(Cl)N1CCOC1=O.O[C:10]([c:9]1[cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[c:38]([O:39][CH3:40])[cH:37][cH:36]1)=[O:11].[NH:12]([CH2:13][C@H:14]1[CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][C@H:25]1[CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH:33]([CH3:34])[CH3:35] | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][c:9]([C:10](=[O:11])[N:12]([CH2:13][C@H:14]2[CH2:15][N:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][C@H:25]2[CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH:33]([CH3:34])[CH3:35])[cH:36][cH:37][c:38]1[O:39][CH3:40] | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 11438d3fa968bbd8c4f3372ffee303c561281eed4a1be36b1ce3c5b0 | 1 | 1 | CCN(CC)CC.ClCCl.O=C1OCCN1P(=O)(Cl)N1CCOC1=O | 44 |
131,095 | 478,582 | 807,174 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].[C:12](OC(=O)C)(=[O:14])[CH3:13].O>N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C:12](=[O:14])[CH3:13])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1 | |f:4.5.6| | US07276512B2_0287 | 2,007 | CC(=O)O[C:7]([CH3:8])=[O:9].O.O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:10][c:11]([O:12][CH3:13])[cH:14]1.[Na+].[Na+].c1ccncc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7]([CH3:8])=[O:9])[cH:10][c:11]([O:12][CH3:13])[cH:14]1 | 0.552534 | CC(=O)OC(C)=O.COc1cc(N)cc(OC)c1.O.O=C([O-])[O-]~[Na+]~[Na+].c1ccncc1>>COc1cc(NC(C)=O)cc(OC)c1 | CC(=O)OC(C)=O.COc1cc(N)cc(OC)c1.O.O=C([O-])[O-].[Na+].[Na+].c1ccncc1>>COc1cc(NC(C)=O)cc(OC)c1 | US07276512B2_0287grants | 90813b414c43d731d9437a1613ff34a5f692465e2eb896d47204ba10 | CC(=O)O[C:7]([CH3:8])=[O:9].O.O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:10][c:11]([O:12][CH3:13])[cH:14]1.[Na+].[Na+].c1ccncc1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7]([CH3:8])=[O:9])[cH:10][c:11]([O:12][CH3:13])[cH:14]1 | ([C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | b7e22e0d3d1463b4dc5e2b14e7859b2f12659f363512c586286db1a5 | 1 | 1 | O.O=C([O-])[O-].[Na+].[Na+].c1ccncc1 | 6 |
116,021 | 433,982 | 738,892 | [CH2:1]([O:8][N:9]=[CH:10][C:11]1[C:12]([F:22])=[C:13]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH3:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:23]([O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([F:21])[C:19]([F:20])=[C:11]([CH:10]=[N:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]=1[F:22])[CH3:24] | |f:2.3| | US07094780B1_0605 | 2,006 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl.O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24] | 0.751302 | CCN=C=NCCCN(C)C~Cl.CCO.CN(C)c1ccncc1.ClCCl.O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F>>CCOC(=O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | CCN=C=NCCCN(C)C.CCO.CN(C)c1ccncc1.Cl.ClCCl.O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F>>CCOC(=O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | US07094780B1_0605grants | fd176860e297d0c3e6421d0a01e527fc6810027f2bc2604b9ff61980 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl.O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24] | ([C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4]=[O;D1;H0:3])>>(O-[CH2;D2;+0:1]-[C;D1;H3:2]).([O;D1;H0:3]=[C:4]-[OH;D1;+0:5]) | bc7193984167c71913195a0abce257da8748eb7d4b76769dceef2d3f | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)c1ccncc1.Cl.ClCCl | 47 |
375,646 | 855,847 | null | [F:1][C:2]([F:30])([F:29])[C:3]1[CH:28]=[CH:27][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:5][CH:4]=1.Cl.Cl.[N:33]1([CH2:38][CH2:39][C@H:40]2[CH2:45][CH2:44][C@H:43]([NH2:46])[CH2:42][CH2:41]2)[CH2:37][CH2:36][CH2:35][CH2:34]1>>[N:33]1([CH2:38][CH2:39][C@H:40]2[CH2:41][CH2:42][C@H:43]([NH:46][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([S:15](=[O:16])(=[O:17])[NH:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[O:7][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:29])([F:1])[F:30])=[CH:28][CH:27]=4)=[CH:19][CH:20]=3)[CH2:44][CH2:45]2)[CH2:37][CH2:36][CH2:35][CH2:34]1 | |f:1.2.3| | US20100075978A1_0307 | 2,010 | Cl.Cl.O[C:2](=[O:1])[c:17]1[cH:18][cH:19][c:20]([S:21](=[O:22])(=[O:23])[NH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[O:31][c:32]2[cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]2)[cH:42][cH:43]1.[NH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c:20]([S:21](=[O:22])(=[O:23])[NH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[O:31][c:32]2[cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]2)[cH:42][cH:43]1 | 0.11863 | Cl~Cl~N[C@@H]1CC[C@@H](CCN2CCCC2)CC1.O=C(O)c1ccc(S(=O)(=O)Nc2ccccc2Oc2ccc(C(F)(F)F)cc2)cc1>>O=C(N[C@@H]1CC[C@@H](CCN2CCCC2)CC1)c1ccc(S(=O)(=O)Nc2ccccc2Oc2ccc(C(F)(F)F)cc2)cc1 | Cl.Cl.N[C@@H]1CC[C@@H](CCN2CCCC2)CC1.O=C(O)c1ccc(S(=O)(=O)Nc2ccccc2Oc2ccc(C(F)(F)F)cc2)cc1>>O=C(N[C@@H]1CC[C@@H](CCN2CCCC2)CC1)c1ccc(S(=O)(=O)Nc2ccccc2Oc2ccc(C(F)(F)F)cc2)cc1 | US20100075978A1_0307apps | aa88a524c3a6b0c759961bda6e283cd6689030f958dc6d34f567b6c4 | Cl.Cl.O[C:2](=[O:1])[c:17]1[cH:18][cH:19][c:20]([S:21](=[O:22])(=[O:23])[NH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[O:31][c:32]2[cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]2)[cH:42][cH:43]1.[NH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]1 | [O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c:20]([S:21](=[O:22])(=[O:23])[NH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[O:31][c:32]2[cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40][cH:41]2)[cH:42][cH:43]1 | ([#7:8]-[#16:7](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:13]):[c:12]:[c:11]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6](-[#16:7](-[#7:8])(=[O;D1;H0:9])=[O;D1;H0:10]):[c:11]:[c:12]:1).([C:13]-[NH2;D1;+0:14]) | fe8fd126c3e948308ab30190d372ade26d9a719816f5a0fafc0536cc | 1 | 1 | Cl.Cl | 835 |
348,482 | 446,501 | null | [F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH2:15](O)[CH3:16]>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1 | null | US20070078121A1_1120 | 2,007 | O=S(Cl)Cl.O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | 0.673337 | CCO.O=C(O)c1ccc(F)cc1.O=S(Cl)Cl>>CCOC(=O)c1ccc(F)cc1 | CCO.O=C(O)c1ccc(F)cc1.O=S(Cl)Cl>>CCOC(=O)c1ccc(F)cc1 | US20070078121A1_1120apps | 121347e4b12e86e27fd27e231ed587f0367d33aff60a0f1aa069e202 | O=S(Cl)Cl.O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.[CH3:1][CH2:2][OH:3] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[OH;D1;+0:5]) | 462ff262701550e8361ae350b730fe337624136bbbc825e08432a1b4 | 1 | 1 | O=S(Cl)Cl | 33 |
427,654 | 1,819,716 | null | Br[C:2]1[CH:3]=[N:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C([O-])(=O)C.[K+].[CH3:16][C:17]1([CH3:33])[C:21]([CH3:23])([CH3:22])[O:20][B:19]([B:19]2[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:33])([CH3:16])[O:18]2)[O:18]1.O1CCOCC1.ClCCl>>[CH3:10][C:5]1[N:4]=[CH:3][C:2]([B:19]2[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:33])([CH3:16])[O:18]2)=[CH:9][C:6]=1[C:7]#[N:8] | |f:1.2| | US20160009720A1_0667 | 2,016 | Br[c:5]1[cH:4][n:3][c:2]([CH3:1])[c:16]([C:17]#[N:18])[cH:15]1.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[O:14]2)OC1(C)C.ClCCl.[K+]>>[CH3:1][c:2]1[n:3][cH:4][c:5]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[O:14]2)[cH:15][c:16]1[C:17]#[N:18] | 0.240414 | C1COCCO1.CC(=O)[O-]~[K+].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.Cc1ncc(Br)cc1C#N.ClCCl>>Cc1ncc(B2OC(C)(C)C(C)(C)O2)cc1C#N | C1COCCO1.CC(=O)[O-].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.Cc1ncc(Br)cc1C#N.ClCCl.[K+]>>Cc1ncc(B2OC(C)(C)C(C)(C)O2)cc1C#N | US20160009720A1_0667apps | 5ce946407a556903d15c4eae7e972a2382a91bdc7d58aa0908c84864 | Br[c:5]1[cH:4][n:3][c:2]([CH3:1])[c:16]([C:17]#[N:18])[cH:15]1.C1COCCO1.CC(=O)[O-].CC1(C)OB([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[O:14]2)OC1(C)C.ClCCl.[K+] | [CH3:1][c:2]1[n:3][cH:4][c:5]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:12])([CH3:13])[O:14]2)[cH:15][c:16]1[C:17]#[N:18] | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[B;H0;D3;+0:5](-[#8:6])-[#8:7])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).(C-C1(-C)-O-B(-[B;H0;D3;+0:5](-[#8:6])-[#8:7])-O-C-1(-C)-C) | 808e890f2f43b90a5b0eed0ef7baa55ba58f5094e250e99d4272ebcc | 1 | 1 | C1COCCO1.CC(=O)[O-].ClCCl.[K+] | 943 |
65,675 | 274,911 | 466,182 | [C:1]([C:4]1[C:5]([CH3:31])=[CH:6][C:7]([O:29][CH3:30])=[C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[C:5]([CH3:31])=[CH:6][C:7]([O:29][CH3:30])=[C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH:9]=1)[CH3:2] | |f:1.2| | US06028195_ | 2,000 | CCO.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][c:19]([C:20]([CH3:21])=[O:22])[c:23]([CH3:24])[cH:25][c:26]3[O:27][CH3:28])[CH2:29][CH2:30]2)[cH:31]1.[Na+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][c:19]([CH:20]([CH3:21])[OH:22])[c:23]([CH3:24])[cH:25][c:26]3[O:27][CH3:28])[CH2:29][CH2:30]2)[cH:31]1 | 0.874584 | CCO.COc1cc(OC)cc(N2CCN(C(=O)Nc3cc(C(C)=O)c(C)cc3OC)CC2)c1.[BH4-]~[Na+]>>COc1cc(OC)cc(N2CCN(C(=O)Nc3cc(C(C)O)c(C)cc3OC)CC2)c1 | CCO.COc1cc(OC)cc(N2CCN(C(=O)Nc3cc(C(C)=O)c(C)cc3OC)CC2)c1.[BH4-].[Na+]>>COc1cc(OC)cc(N2CCN(C(=O)Nc3cc(C(C)O)c(C)cc3OC)CC2)c1 | US06028195_grants | 4a24241f799a5b0955ff9c3360df329ad9c705dc577e172761d6fc84 | CCO.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][c:19]([C:20]([CH3:21])=[O:22])[c:23]([CH3:24])[cH:25][c:26]3[O:27][CH3:28])[CH2:29][CH2:30]2)[cH:31]1.[Na+] | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([C:14](=[O:15])[NH:16][c:17]3[cH:18][c:19]([CH:20]([CH3:21])[OH:22])[c:23]([CH3:24])[cH:25][c:26]3[O:27][CH3:28])[CH2:29][CH2:30]2)[cH:31]1 | ([C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4])>>([C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]) | e79b9f0e956cb38254670cbba4f53d0c22148efe9b15465e130440fe | 1 | 1 | CCO.[BH4-].[Na+] | 24 |
144,538 | 518,752 | 869,627 | [F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH2:25][C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[C:16]([C:19]([O:21]CC)=[O:20])[NH:17][N:18]=3)[CH:9]=2)[CH:7]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH2:25][C:26]([F:34])([F:35])[C:27]([F:33])([F:32])[C:28]([F:30])([F:31])[F:29])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[C:16]([C:19]([OH:21])=[O:20])[NH:17][N:18]=3)[CH:9]=2)[CH:7]=1 | |f:1.2| | US07459475B2_0366 | 2,008 | CC[O:3][C:2](=[O:1])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[O:19][CH2:20][C:21]([F:22])([F:23])[C:24]([F:25])([F:26])[C:27]([F:28])([F:29])[F:30])[cH:31]2)[n:32][nH:33]1.CO.Cl.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[O:19][CH2:20][C:21]([F:22])([F:23])[C:24]([F:25])([F:26])[C:27]([F:28])([F:29])[F:30])[cH:31]2)[n:32][nH:33]1 | 0.114792 | CCOC(=O)c1nc(-c2cccc(-c3cc(F)ccc3OCC(F)(F)C(F)(F)C(F)(F)F)c2)n[nH]1.CO.Cl.[Na+]~[OH-]>>O=C(O)c1nc(-c2cccc(-c3cc(F)ccc3OCC(F)(F)C(F)(F)C(F)(F)F)c2)n[nH]1 | CCOC(=O)c1nc(-c2cccc(-c3cc(F)ccc3OCC(F)(F)C(F)(F)C(F)(F)F)c2)n[nH]1.CO.Cl.[Na+].[OH-]>>O=C(O)c1nc(-c2cccc(-c3cc(F)ccc3OCC(F)(F)C(F)(F)C(F)(F)F)c2)n[nH]1 | US07459475B2_0366grants | a30cabd0544560b39b65d93ee91b404a9772b4ca70718a12e036dcab | CC[O:3][C:2](=[O:1])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[O:19][CH2:20][C:21]([F:22])([F:23])[C:24]([F:25])([F:26])[C:27]([F:28])([F:29])[F:30])[cH:31]2)[n:32][nH:33]1.CO.Cl.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]3[O:19][CH2:20][C:21]([F:22])([F:23])[C:24]([F:25])([F:26])[C:27]([F:28])([F:29])[F:30])[cH:31]2)[n:32][nH:33]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b8d35231a9d964a0bcde41cb860d8e6c4726c2823ff5946d3ed0c3c9 | 1 | 1 | CO.Cl.[Na+].[OH-] | 171 |
146,807 | 526,066 | 881,568 | [C:1]([C:3]1[CH:4]=[C:5]([CH:38]=[CH:39][CH:40]=1)[CH2:6][N:7]([CH:17]1[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]2[C:30]([CH3:36])=[N:31][CH:32]=[N:33][C:34]=2[CH3:35])=[O:28])[CH2:19][CH2:18]1)[C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)#[N:2].Cl.[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH2:46]>>[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH:46][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([N:7]([CH2:6][C:5]2[CH:38]=[CH:39][CH:40]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:37])[CH2:24][CH2:25][NH:26][C:27]([C:29]3[C:34]([CH3:35])=[N:33][CH:32]=[N:31][C:30]=3[CH3:36])=[O:28])[CH2:19][CH2:18]2)=[CH:9][CH:10]=1 | |f:1.2| | US07491735B2_1069 | 2,009 | Cl.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22]2)[CH:23]2[CH2:24][CH2:25][N:26]([CH:27]([CH3:28])[CH2:29][CH2:30][NH:31][C:32](=[O:33])[c:34]3[c:35]([CH3:36])[n:37][cH:38][n:39][c:40]3[CH3:41])[CH2:42][CH2:43]2)[cH:44][cH:45]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH2:6]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22]2)[CH:23]2[CH2:24][CH2:25][N:26]([CH:27]([CH3:28])[CH2:29][CH2:30][NH:31][C:32](=[O:33])[c:34]3[c:35]([CH3:36])[n:37][cH:38][n:39][c:40]3[CH3:41])[CH2:42][CH2:43]2)[cH:44][cH:45]1 | 0.613811 | COC(=O)CN~Cl.Cc1ncnc(C)c1C(=O)NCCC(C)N1CCC(N(Cc2cccc(C#N)c2)c2ccc(C(=O)O)cc2)CC1>>COC(=O)CNC(=O)c1ccc(N(Cc2cccc(C#N)c2)C2CCN(C(C)CCNC(=O)c3c(C)ncnc3C)CC2)cc1 | COC(=O)CN.Cc1ncnc(C)c1C(=O)NCCC(C)N1CCC(N(Cc2cccc(C#N)c2)c2ccc(C(=O)O)cc2)CC1.Cl>>COC(=O)CNC(=O)c1ccc(N(Cc2cccc(C#N)c2)C2CCN(C(C)CCNC(=O)c3c(C)ncnc3C)CC2)cc1 | US07491735B2_1069grants | d4a7d4be6dbba41224ff9cc0cd21996168d13ed31ffacedb55a38ff5 | Cl.O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22]2)[CH:23]2[CH2:24][CH2:25][N:26]([CH:27]([CH3:28])[CH2:29][CH2:30][NH:31][C:32](=[O:33])[c:34]3[c:35]([CH3:36])[n:37][cH:38][n:39][c:40]3[CH3:41])[CH2:42][CH2:43]2)[cH:44][cH:45]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH2:6] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][c:19]([C:20]#[N:21])[cH:22]2)[CH:23]2[CH2:24][CH2:25][N:26]([CH:27]([CH3:28])[CH2:29][CH2:30][NH:31][C:32](=[O:33])[c:34]3[c:35]([CH3:36])[n:37][cH:38][n:39][c:40]3[CH3:41])[CH2:42][CH2:43]2)[cH:44][cH:45]1 | ([C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH2;D1;+0:9]) | 8eba64e9b8380cd5216a5675f278670915caad6c889cde2b52fe0db2 | 1 | 1 | Cl | 652 |
408,850 | 1,601,200 | null | [CH3:1][C:2]1[C:7]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=O)=[CH:16][C:10]=3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH2:29])=[C:24]([CH3:36])[CH:23]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:29][C:18](=[O:20])[CH2:17][C:15]2[CH:14]=[CH:13][C:11]3[NH:12][C:8]([C:7]4[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=4)=[N:9][C:10]=3[CH:16]=2)=[C:24]([CH3:36])[CH:23]=1 | null | US20140315881A1_0945 | 2,014 | O[C:11](=[O:12])[CH2:13][c:14]1[cH:15][cH:16][c:17]2[nH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][n:24][c:25]3[CH3:26])[n:27][c:28]2[cH:29]1.[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH2:10])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH:10][C:11](=[O:12])[CH2:13][c:14]1[cH:15][cH:16][c:17]2[nH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][n:24][c:25]3[CH3:26])[n:27][c:28]2[cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1 | 0.870963 | Cc1cc(Cl)ccc1C(N)c1ccccc1.Cc1ncccc1-c1nc2cc(CC(=O)O)ccc2[nH]1>>Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2[nH]c(-c3cccnc3C)nc2c1)c1ccccc1 | Cc1cc(Cl)ccc1C(N)c1ccccc1.Cc1ncccc1-c1nc2cc(CC(=O)O)ccc2[nH]1>>Cc1cc(Cl)ccc1C(NC(=O)Cc1ccc2[nH]c(-c3cccnc3C)nc2c1)c1ccccc1 | US20140315881A1_0945apps | 6e8aefb557bba6be1a5b2bb30321d8d2a32142327909017d236427a4 | O[C:11](=[O:12])[CH2:13][c:14]1[cH:15][cH:16][c:17]2[nH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][n:24][c:25]3[CH3:26])[n:27][c:28]2[cH:29]1.[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH2:10])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1 | [CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][cH:7][c:8]1[CH:9]([NH:10][C:11](=[O:12])[CH2:13][c:14]1[cH:15][cH:16][c:17]2[nH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][n:24][c:25]3[CH3:26])[n:27][c:28]2[cH:29]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5](-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)-[c:12]1:[c:13]:[c:14]:[c:15]:[c:16]:[c:17]:1)>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5](-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)-[c:12]1:[c:13]:[c:14]:[c:15]:[c:16]:[c:17]:1) | a7de99e9470b4eb4268b92ce4627e5b055b5d25de5ec99d8ddb9f3dc | 1 | 1 | null | 769 |
231,631 | 774,131 | 1,276,665 | N1C2C(=CC([NH:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:21][CH2:22][C:23](O)=[O:24])[CH:19]=4)[N:14]=[C:13]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:29]=4)[N:12]=3)=CC=2)C=N1.C1CN([P+](ON2[N:65]=[N:64][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:73]CN(C(C)C)C(C)C.[CH3:82][N:83]1[CH2:88][CH2:87][NH:86][CH2:85][CH2:84]1>CN(C=O)C.C(Cl)Cl>[NH:64]1[C:59]2[C:58](=[CH:63][C:62]([NH:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:21][CH2:22][C:23]([N:86]5[CH2:87][CH2:88][N:83]([CH3:82])[CH2:84][CH2:85]5)=[O:24])[CH:19]=4)[N:14]=[C:13]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:29]=4)[N:12]=3)=[CH:61][CH:60]=2)[CH:73]=[N:65]1 | |f:1.2| | US08357693B2_0754 | 2,013 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F.O[C:37]([CH2:36][O:35][c:34]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19]3)[n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][c:26]4[nH:27][n:28][cH:29][c:30]4[cH:31]3)[c:32]2[cH:33]1)=[O:38].[NH:39]1[CH2:40][CH2:41][N:42]([CH3:43])[CH2:44][CH2:45]1.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19]3)[n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][c:26]4[nH:27][n:28][cH:29][c:30]4[cH:31]3)[c:32]2[cH:33][c:34]1[O:35][CH2:36][C:37](=[O:38])[N:39]1[CH2:40][CH2:41][N:42]([CH3:43])[CH2:44][CH2:45]1 | 0.691741 | CCN(C(C)C)C(C)C.CN(C)C=O.CN1CCNCC1.COc1cc2nc(-c3cccc(-c4ccccc4)c3)nc(Nc3ccc4[nH]ncc4c3)c2cc1OCC(=O)O.ClCCl.F[P-](F)(F)(F)(F)F~c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>COc1cc2nc(-c3cccc(-c4ccccc4)c3)nc(Nc3ccc4[nH]ncc4c3)c2cc1OCC(=O)N1CCN(C)CC1 | CCN(C(C)C)C(C)C.CN(C)C=O.CN1CCNCC1.COc1cc2nc(-c3cccc(-c4ccccc4)c3)nc(Nc3ccc4[nH]ncc4c3)c2cc1OCC(=O)O.ClCCl.F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>COc1cc2nc(-c3cccc(-c4ccccc4)c3)nc(Nc3ccc4[nH]ncc4c3)c2cc1OCC(=O)N1CCN(C)CC1 | US08357693B2_0754grants | facae423da750685a1fa9f2f0e9223a0ffdd2641a6c5a542de49199d | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F.O[C:37]([CH2:36][O:35][c:34]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19]3)[n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][c:26]4[nH:27][n:28][cH:29][c:30]4[cH:31]3)[c:32]2[cH:33]1)=[O:38].[NH:39]1[CH2:40][CH2:41][N:42]([CH3:43])[CH2:44][CH2:45]1.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19]3)[n:20][c:21]([NH:22][c:23]3[cH:24][cH:25][c:26]4[nH:27][n:28][cH:29][c:30]4[cH:31]3)[c:32]2[cH:33][c:34]1[O:35][CH2:36][C:37](=[O:38])[N:39]1[CH2:40][CH2:41][N:42]([CH3:43])[CH2:44][CH2:45]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.F[P-](F)(F)(F)(F)F.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | 146 |
267,860 | 881,105 | 1,467,285 | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]3=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>>[CH3:24][CH:23]([CH3:25])[C@H:18]([N:13]1[CH2:12][C:11]2[C:15](=[CH:16][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:34]([NH:33][C:30]4[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=4)=[O:35])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[C:14]1=[O:17])[C:19]([O:21][CH3:22])=[O:20] | null | US08748426B2_1420 | 2,014 | [C:20](=[O:21])=[N:22][c:23]1[cH:24][cH:25][c:26]([CH3:27])[cH:28][cH:29]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH:6]([CH3:7])[CH3:8])[N:9]1[CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:30][cH:31]3)[cH:32][c:33]2[C:34]1=[O:35]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH:6]([CH3:7])[CH3:8])[N:9]1[CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[NH:22][c:23]4[cH:24][cH:25][c:26]([CH3:27])[cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][c:33]2[C:34]1=[O:35] | 0.636602 | COC(=O)[C@H](C(C)C)N1Cc2ccc(-c3ccc(N)cc3)cc2C1=O.Cc1ccc(N=C=O)cc1>>COC(=O)[C@H](C(C)C)N1Cc2ccc(-c3ccc(NC(=O)Nc4ccc(C)cc4)cc3)cc2C1=O | COC(=O)[C@H](C(C)C)N1Cc2ccc(-c3ccc(N)cc3)cc2C1=O.Cc1ccc(N=C=O)cc1>>COC(=O)[C@H](C(C)C)N1Cc2ccc(-c3ccc(NC(=O)Nc4ccc(C)cc4)cc3)cc2C1=O | US08748426B2_1420grants | d665a2c8917372e96e4f557a03eee27a9792e66f5c3b0561705f3dc6 | [C:20](=[O:21])=[N:22][c:23]1[cH:24][cH:25][c:26]([CH3:27])[cH:28][cH:29]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH:6]([CH3:7])[CH3:8])[N:9]1[CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:30][cH:31]3)[cH:32][c:33]2[C:34]1=[O:35] | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH:6]([CH3:7])[CH3:8])[N:9]1[CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[NH:22][c:23]4[cH:24][cH:25][c:26]([CH3:27])[cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][c:33]2[C:34]1=[O:35] | ([O;D1;H0:3]=[C;H0;D3;+0:4](-[NH;D2;+0:1]-[c:2])-[NH;D2;+0:5]-[c:6])>>([NH2;D1;+0:1]-[c:2]).([O;D1;H0:3]=[C;H0;D2;+0:4]=[N;H0;D2;+0:5]-[c:6]) | 4d90b1ac49508f74aabfac353704d5bbc882a25d954d104bc3fe56df | 0.5 | 2 | null | 473 |
196,056 | 671,824 | 1,110,364 | [I:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)CCl.C1C=[N:21]C2N(O)N=NC=2C=1.[Cl-].[NH4+].CCN(C(C)C)C(C)C>CN(C=O)C.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH2:21])=[O:8] | |f:3.4| | US08017601B2_0223 | 2,011 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.O[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([I:7])[cH:8]1)=[O:12].On1nnc2cccnc21.[Cl-].[NH4+:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([I:7])[cH:8][c:9]1[C:10]([NH2:11])=[O:12] | 0.845812 | CCN(C(C)C)C(C)C.CN(C)C=O.COc1ccc(I)cc1C(=O)O.ClCCCl.O.On1nnc2cccnc21.[Cl-]~[NH4+]>>COc1ccc(I)cc1C(N)=O | CCN(C(C)C)C(C)C.CN(C)C=O.COc1ccc(I)cc1C(=O)O.ClCCCl.O.On1nnc2cccnc21.[Cl-].[NH4+]>>COc1ccc(I)cc1C(N)=O | US08017601B2_0223grants | 4508fa4098c6286340eaf759f0a42da47fb24920fa3f3614cc87fe24 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.O[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([I:7])[cH:8]1)=[O:12].On1nnc2cccnc21.[Cl-].[NH4+:11] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([I:7])[cH:8][c:9]1[C:10]([NH2:11])=[O:12] | ([NH2;D1;+0:4]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH4+;D0:4]) | c421fff6c68457e5a1b10b45c638efef86b6256b0ea7f128ff2943ad | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCCl.O.On1nnc2cccnc21.[Cl-] | 358 |
247,812 | 822,985 | 1,363,710 | [F:1][C:2]([F:22])([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH3:21])=[CH:13]2)[C:3]([O:5]C(C)(C)C)=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[F:22][C:2]([F:1])([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH3:21])=[CH:13]2)[C:3]([OH:5])=[O:4] | null | US08524900B2_0965 | 2,013 | CC(C)(C)[O:15][C:13]([C:10]([c:9]1[cH:8][cH:7][c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[cH:18][c:17]2[cH:16]1)([F:11])[F:12])=[O:14].CC[SiH](CC)CC.ClCCl.O=C(O)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[C:13](=[O:14])[OH:15])[cH:16][c:17]2[cH:18]1 | 0.6762 | CC[SiH](CC)CC.COc1cnc2ccc(C(F)(F)C(=O)OC(C)(C)C)cc2c1.ClCCl.O=C(O)C(F)(F)F>>COc1cnc2ccc(C(F)(F)C(=O)O)cc2c1 | CC[SiH](CC)CC.COc1cnc2ccc(C(F)(F)C(=O)OC(C)(C)C)cc2c1.ClCCl.O=C(O)C(F)(F)F>>COc1cnc2ccc(C(F)(F)C(=O)O)cc2c1 | US08524900B2_0965grants | a2addda8897cddcc19f3fc8f90b891ee490460854c658057c3656d5e | CC(C)(C)[O:15][C:13]([C:10]([c:9]1[cH:8][cH:7][c:6]2[n:5][cH:4][c:3]([O:2][CH3:1])[cH:18][c:17]2[cH:16]1)([F:11])[F:12])=[O:14].CC[SiH](CC)CC.ClCCl.O=C(O)C(F)(F)F | [CH3:1][O:2][c:3]1[cH:4][n:5][c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[C:13](=[O:14])[OH:15])[cH:16][c:17]2[cH:18]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | cd4c8dfb74ae00d4ec8387e8837370d2f9fd4ad5e54ff56c9878f839 | 1 | 1 | CC[SiH](CC)CC.ClCCl.O=C(O)C(F)(F)F | 278 |
361,717 | 641,914 | null | [Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>CN(C1C=CN=CC=1)C.ClCCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[N:14]2[CH2:15][CH2:16][N:17]([C:34]([C:33]3[CH:37]=[CH:38][C:30]([F:29])=[CH:31][CH:32]=3)=[O:35])[CH2:18][CH2:19]2)=[CH:4][CH:3]=1 | null | US20080306087A1_0223 | 2,008 | CCN(CC)CC.CN(C)c1ccncc1.ClCCCl.Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1 | 0.591532 | CCN(CC)CC.CN(C)c1ccncc1.ClCCCl.Clc1ccc(C(c2ccc(Cl)cc2)N2CCNCC2)cc1.O=C(Cl)c1ccc(F)cc1>>O=C(c1ccc(F)cc1)N1CCN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)CC1 | CCN(CC)CC.CN(C)c1ccncc1.ClCCCl.Clc1ccc(C(c2ccc(Cl)cc2)N2CCNCC2)cc1.O=C(Cl)c1ccc(F)cc1>>O=C(c1ccc(F)cc1)N1CCN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)CC1 | US20080306087A1_0223apps | 0311efb89e07fea6c10015a43c696d716b41fce7a5eed6ed7339d4b7 | CCN(CC)CC.CN(C)c1ccncc1.ClCCCl.Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 8e776da45ba18fd7625e94abe947f9adcda1a9454a884e9be672df24 | 1 | 1 | CCN(CC)CC.CN(C)c1ccncc1.ClCCCl | 201 |
364,243 | 671,202 | null | [CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([O:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([CH2:24][NH:25]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[N:12]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([O:17][C@H:18]2[CH2:19][CH2:20][C@H:21]([CH2:24][NH2:25])[CH2:22][CH2:23]2)[N:12]=1 | null | US20090054392A1_0396 | 2,009 | CC(C)(C)OC(=O)[NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[cH:22]3)[n:23]2)[CH2:24][CH2:25]1.ClCCl.O=C(O)C(F)(F)F>>[NH2:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[cH:22]3)[n:23]2)[CH2:24][CH2:25]1 | 0.976865 | CC(C)(C)OC(=O)NC[C@@H]1CC[C@@H](Oc2nccc(-c3ccc4ccccc4c3)n2)CC1.ClCCl.O=C(O)C(F)(F)F>>NC[C@@H]1CC[C@@H](Oc2nccc(-c3ccc4ccccc4c3)n2)CC1 | CC(C)(C)OC(=O)NC[C@@H]1CC[C@@H](Oc2nccc(-c3ccc4ccccc4c3)n2)CC1.ClCCl.O=C(O)C(F)(F)F>>NC[C@@H]1CC[C@@H](Oc2nccc(-c3ccc4ccccc4c3)n2)CC1 | US20090054392A1_0396apps | 1f50e63668428a43d27caa61276b45f510c7a1f7681c270b01cd2ca2 | CC(C)(C)OC(=O)[NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[cH:22]3)[n:23]2)[CH2:24][CH2:25]1.ClCCl.O=C(O)C(F)(F)F | [NH2:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]4[cH:22]3)[n:23]2)[CH2:24][CH2:25]1 | ([C:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]) | 6c83f45f485301792011c63e6835be21ece3be24f5b32a6e45acc5be | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 538 |
342,344 | 349,368 | null | Br[C:2]1[CH:3]=[CH:4][C:5]([OH:26])=[C:6]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]([N:19]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH3:20])=[O:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:7]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O1CCOCC1>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][N:19]([CH3:20])[C:17]([C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([C:6]3[CH:7]=[C:2]([C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([O:28][CH3:27])[CH:34]=4)[CH:3]=[CH:4][C:5]=3[OH:26])[S:9][C:10]=2[CH:16]=1)=[O:18] | |f:2.3.4| | US20060106015A1_0237 | 2,006 | Br[c:8]1[cH:9][cH:10][c:11]([OH:12])[c:13](-[c:14]2[n:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]([CH3:23])[CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[cH:29][c:30]3[s:31]2)[cH:32]1.C1COCCO1.CCO.O=C([O-])[O-].OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]1.[Na+].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13](-[c:14]3[n:15][c:16]4[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]([CH3:23])[CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[cH:29][c:30]4[s:31]3)[cH:32]2)[cH:33]1 | 0.756939 | C1COCCO1.CCO.CN(C)CCN(C)C(=O)c1ccc2nc(-c3cc(Br)ccc3O)sc2c1.COc1cccc(B(O)O)c1.O=C([O-])[O-]~[Na+]~[Na+]>>COc1cccc(-c2ccc(O)c(-c3nc4ccc(C(=O)N(C)CCN(C)C)cc4s3)c2)c1 | C1COCCO1.CCO.CN(C)CCN(C)C(=O)c1ccc2nc(-c3cc(Br)ccc3O)sc2c1.COc1cccc(B(O)O)c1.O=C([O-])[O-].[Na+].[Na+]>>COc1cccc(-c2ccc(O)c(-c3nc4ccc(C(=O)N(C)CCN(C)C)cc4s3)c2)c1 | US20060106015A1_0237apps | a19740a6533ee4bd83000222cec05e0b1f13da0fd4b143a5a18a9e13 | Br[c:8]1[cH:9][cH:10][c:11]([OH:12])[c:13](-[c:14]2[n:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]([CH3:23])[CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[cH:29][c:30]3[s:31]2)[cH:32]1.C1COCCO1.CCO.O=C([O-])[O-].OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]1.[Na+].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([OH:12])[c:13](-[c:14]3[n:15][c:16]4[cH:17][cH:18][c:19]([C:20](=[O:21])[N:22]([CH3:23])[CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[cH:29][c:30]4[s:31]3)[cH:32]2)[cH:33]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 55251936defc26e51bebc585e4f1cda158e89f53686fa5d9c09591aa | 0.5 | 2 | C1COCCO1.CCO.O=C([O-])[O-].[Na+].[Na+] | 837 |
149,588 | 535,302 | 896,308 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]2[C:15]1[N:37](S(C2C=CC(C)=CC=2)(=O)=O)[C:18]2=[N:19][CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[C:17]2[CH:16]=1.[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH3:14])[CH:7]=[C:6]2[C:15]1[NH:37][C:18]2=[N:19][CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25]3[CH:26]=[CH:27][C:28]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)=[CH:29][CH:30]=3)=[C:17]2[CH:16]=1 | |f:1.2| | US07528147B2_1222 | 2,009 | Cc1ccc(S(=O)(=O)[n:29]2[c:7](-[c:6]3[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH3:37])[cH:34][c:33]4[n:31]([CH3:32])[cH:30]3)[cH:8][c:9]3[c:10]([CH2:11][NH:12][c:13]4[cH:14][cH:15][c:16]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[cH:23][cH:24]4)[cH:25][cH:26][n:27][c:28]32)cc1.[K+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](-[c:7]3[cH:8][c:9]4[c:10]([CH2:11][NH:12][c:13]5[cH:14][cH:15][c:16]([N:17]6[CH2:18][CH2:19][O:20][CH2:21][CH2:22]6)[cH:23][cH:24]5)[cH:25][cH:26][n:27][c:28]4[nH:29]3)[cH:30][n:31]([CH3:32])[c:33]2[cH:34][c:35]1[O:36][CH3:37] | 0.914049 | COc1cc2c(-c3cc4c(CNc5ccc(N6CCOCC6)cc5)ccnc4n3S(=O)(=O)c3ccc(C)cc3)cn(C)c2cc1OC.[K+]~[OH-]>>COc1cc2c(-c3cc4c(CNc5ccc(N6CCOCC6)cc5)ccnc4[nH]3)cn(C)c2cc1OC | COc1cc2c(-c3cc4c(CNc5ccc(N6CCOCC6)cc5)ccnc4n3S(=O)(=O)c3ccc(C)cc3)cn(C)c2cc1OC.[K+].[OH-]>>COc1cc2c(-c3cc4c(CNc5ccc(N6CCOCC6)cc5)ccnc4[nH]3)cn(C)c2cc1OC | US07528147B2_1222grants | 06ca1039278df162265132febeb873c348dee9afcbb81246b650c608 | Cc1ccc(S(=O)(=O)[n:29]2[c:7](-[c:6]3[c:5]4[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH3:37])[cH:34][c:33]4[n:31]([CH3:32])[cH:30]3)[cH:8][c:9]3[c:10]([CH2:11][NH:12][c:13]4[cH:14][cH:15][c:16]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[cH:23][cH:24]4)[cH:25][cH:26][n:27][c:28]32)cc1.[K+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](-[c:7]3[cH:8][c:9]4[c:10]([CH2:11][NH:12][c:13]5[cH:14][cH:15][c:16]([N:17]6[CH2:18][CH2:19][O:20][CH2:21][CH2:22]6)[cH:23][cH:24]5)[cH:25][cH:26][n:27][c:28]4[nH:29]3)[cH:30][n:31]([CH3:32])[c:33]2[cH:34][c:35]1[O:36][CH3:37] | ([#7;a:4]:[c:3]:[nH;D2;+0:1]:[c:2])>>(C-c1:c:c:c(-S(=O)(=O)-[n;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]):c:c:1) | c95de80e5a6f2ae02af354bd3de965db6b65a0244ac97425e4f9cbfb | 1 | 1 | [K+].[OH-] | 949 |
158,683 | 562,748 | 938,954 | [NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C[O:9][C:10](=O)[CH:11]([Cl:13])[CH3:12]>>[Cl:13][CH:11]([CH3:12])[C:10]([N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4])=[O:9] | null | US07619050B2_0339 | 2,009 | CO[C:4]([CH:2]([CH3:1])[Cl:3])=[O:5].[NH:6]([CH2:7][CH2:8][OH:9])[CH2:10][CH2:11][OH:12]>>[CH3:1][CH:2]([Cl:3])[C:4](=[O:5])[N:6]([CH2:7][CH2:8][OH:9])[CH2:10][CH2:11][OH:12] | 0.624395 | COC(=O)C(C)Cl.OCCNCCO>>CC(Cl)C(=O)N(CCO)CCO | COC(=O)C(C)Cl.OCCNCCO>>CC(Cl)C(=O)N(CCO)CCO | US07619050B2_0339grants | d1342f7bf8e20a86a55bdc66b5452a7b76d8aa34e2e497fd34275724 | CO[C:4]([CH:2]([CH3:1])[Cl:3])=[O:5].[NH:6]([CH2:7][CH2:8][OH:9])[CH2:10][CH2:11][OH:12] | [CH3:1][CH:2]([Cl:3])[C:4](=[O:5])[N:6]([CH2:7][CH2:8][OH:9])[CH2:10][CH2:11][OH:12] | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 1d52f80c623161a1d23da40bb4e0b48051c37792b5c9cfeff6290e3b | 1 | 1 | null | 227 |
346,180 | 411,809 | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[OH:13]O.[OH-].[NH4+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([O-:13])=[CH:8][CH:7]=[CH:6]2 | |f:2.3| | US20060276481A1_0245 | 2,006 | CC(=O)O.O[OH:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][cH:10][n:11]2)[cH:13]1.[NH4+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][cH:10][n+:11]2[O-:12])[cH:13]1 | 0.525157 | CC(=O)O.COc1ccc2ncccc2c1.OO.[NH4+]~[OH-]>>COc1ccc2c(ccc[n+]2[O-])c1 | CC(=O)O.COc1ccc2ncccc2c1.OO.[NH4+].[OH-]>>COc1ccc2c(ccc[n+]2[O-])c1 | US20060276481A1_0245apps | 26489af5437ebe2494d11f3f2e3bf22b5d647709cbb2787e3368d701 | CC(=O)O.O[OH:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][cH:10][n:11]2)[cH:13]1.[NH4+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8][cH:9][cH:10][n+:11]2[O-:12])[cH:13]1 | ([O-;H0;D1:1]-[n+;H0;D3:3](:[c:2]):[c:4])>>(O-[OH;D1;+0:1]).([c:2]:[n;H0;D2;+0:3]:[c:4]) | d1c1a3d3f46479b7ab32de537a5b5a796062c3c565c677e75b21819c | 1 | 1 | CC(=O)O.[NH4+].[OH-] | 396 |
12,561 | 62,950 | 103,130 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](I)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:10] | |f:2.3.4| | US04367234_ | 1,983 | CC(C)=O.I[CH2:2][CH3:1].O=C([O-])[O-].[K+].[K+].[OH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | 0.935853 | CC(C)=O.CCI.O=C([O-])[O-]~[K+]~[K+].Oc1ccc(Cl)cc1>>CCOc1ccc(Cl)cc1 | CC(C)=O.CCI.O=C([O-])[O-].Oc1ccc(Cl)cc1.[K+].[K+]>>CCOc1ccc(Cl)cc1 | US04367234_grants | 96f61f267d7ba01aceb5877f5fe67444249edf2a5bd0f3235c4a5f62 | CC(C)=O.I[CH2:2][CH3:1].O=C([O-])[O-].[K+].[K+].[OH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1 | ([C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(I-[CH2;D2;+0:1]-[C;D1;H3:2]).([OH;D1;+0:3]-[c:4]) | 56fe1955dd73a88d39d3c4c7e3804dc6559c131a5243e5175c54fb89 | 1 | 1 | CC(C)=O.O=C([O-])[O-].[K+].[K+] | 198 |
185,808 | 642,714 | 1,062,714 | [Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Br.[NH2:15][C:16]1[S:17][C:18]([Br:21])=[CH:19][N:20]=1>N1C=CC=CC=1>[Br:21][C:18]1[S:17][C:16]([NH:15][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[N:20][CH:19]=1 | |f:1.2| | US07910595B2_1027 | 2,011 | Br.Cl[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1.[NH2:3][c:4]1[n:5][cH:6][c:7]([Br:8])[s:9]1.c1ccncc1>>[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][c:7]([Br:8])[s:9]1)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | 0.969798 | Br~Nc1ncc(Br)s1.O=C(Cl)c1ccc(Cl)c([N+](=O)[O-])c1.c1ccncc1>>O=C(Nc1ncc(Br)s1)c1ccc(Cl)c([N+](=O)[O-])c1 | Br.Nc1ncc(Br)s1.O=C(Cl)c1ccc(Cl)c([N+](=O)[O-])c1.c1ccncc1>>O=C(Nc1ncc(Br)s1)c1ccc(Cl)c([N+](=O)[O-])c1 | US07910595B2_1027grants | ceffe6ea763d8a284ea52abc0d3260504b8178327b5627eb2636bde0 | Br.Cl[C:2](=[O:1])[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1.[NH2:3][c:4]1[n:5][cH:6][c:7]([Br:8])[s:9]1.c1ccncc1 | [O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][c:7]([Br:8])[s:9]1)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | ([#16;a:4]:[c:5](:[#7;a:6])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([#16;a:4]:[c:5](:[#7;a:6])-[NH2;D1;+0:7]) | a813c37ea4f3c2de0a7a7c92b82ed0745f05d3b271f39a6c53d90555 | 1 | 1 | Br.c1ccncc1 | 673 |
381,501 | 953,207 | null | [C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][CH2:7][CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C@@:17]2([O:50][CH2:51][CH2:52][NH2:53])[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][C@@H:18]2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]3[O:43][CH2:42][CH2:41][N:40]([CH2:44][CH2:45][CH2:46][O:47][CH3:48])[C:39]=3[CH:49]=2)=[CH:13][CH:12]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:5][O:6][CH2:7][CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C@@:17]2([O:50][CH2:51][CH2:52][NH:53][C:1](=[O:3])[CH3:2])[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)(=[O:24])=[O:25])[CH2:19][C@@H:18]2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]3[O:43][CH2:42][CH2:41][N:40]([CH2:44][CH2:45][CH2:46][O:47][CH3:48])[C:39]=3[CH:49]=2)=[CH:15][CH:16]=1 | |f:3.4| | US20100256146A1_0739 | 2,010 | CCN(CC)CC.ClCCl.Cl[C:36]([CH3:37])=[O:38].O.O=C([O-])O.[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][O:15][C@H:16]3[CH2:17][N:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[CH2:29][CH2:30][C@:31]3([O:32][CH2:33][CH2:34][NH2:35])[c:39]3[cH:40][cH:41][c:42]([CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[cH:49][cH:50]3)[cH:51][c:52]21.[Na+]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][O:15][C@H:16]3[CH2:17][N:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[CH2:29][CH2:30][C@:31]3([O:32][CH2:33][CH2:34][NH:35][C:36]([CH3:37])=[O:38])[c:39]3[cH:40][cH:41][c:42]([CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[cH:49][cH:50]3)[cH:51][c:52]21 | 0.47807 | CC(=O)Cl.CCN(CC)CC.COCCCN1CCOc2ccc(CO[C@H]3CN(S(=O)(=O)c4ccc(C)cc4)CC[C@]3(OCCN)c3ccc(COCCOC)cc3)cc21.ClCCl.O.O=C([O-])O~[Na+]>>COCCCN1CCOc2ccc(CO[C@H]3CN(S(=O)(=O)c4ccc(C)cc4)CC[C@]3(OCCNC(C)=O)c3ccc(COCCOC)cc3)cc21 | CC(=O)Cl.CCN(CC)CC.COCCCN1CCOc2ccc(CO[C@H]3CN(S(=O)(=O)c4ccc(C)cc4)CC[C@]3(OCCN)c3ccc(COCCOC)cc3)cc21.ClCCl.O.O=C([O-])O.[Na+]>>COCCCN1CCOc2ccc(CO[C@H]3CN(S(=O)(=O)c4ccc(C)cc4)CC[C@]3(OCCNC(C)=O)c3ccc(COCCOC)cc3)cc21 | US20100256146A1_0739apps | dd0144c37a0e43b2522bc4e8dbeed40713a386b971d06e8b3408eee4 | CCN(CC)CC.ClCCl.Cl[C:36]([CH3:37])=[O:38].O.O=C([O-])O.[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][O:15][C@H:16]3[CH2:17][N:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[CH2:29][CH2:30][C@:31]3([O:32][CH2:33][CH2:34][NH2:35])[c:39]3[cH:40][cH:41][c:42]([CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[cH:49][cH:50]3)[cH:51][c:52]21.[Na+] | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][O:15][C@H:16]3[CH2:17][N:18]([S:19](=[O:20])(=[O:21])[c:22]4[cH:23][cH:24][c:25]([CH3:26])[cH:27][cH:28]4)[CH2:29][CH2:30][C@:31]3([O:32][CH2:33][CH2:34][NH:35][C:36]([CH3:37])=[O:38])[c:39]3[cH:40][cH:41][c:42]([CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[cH:49][cH:50]3)[cH:51][c:52]21 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | CCN(CC)CC.ClCCl.O.O=C([O-])O.[Na+] | 45 |
275,710 | 904,342 | 1,507,903 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[O:16][C:15]([CH3:17])=[N:14][CH:13]=1)[C:6](O)=[O:7].O.[NH2:19][NH2:20]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[O:16][C:15]([CH3:17])=[N:14][CH:13]=1)[C:6]([NH:19][NH2:20])=[O:7] | |f:1.2| | US08822699B2_0745 | 2,014 | C1CCOC1.O.O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12](-[c:13]2[cH:14][n:15][c:16]([CH3:17])[o:18]2)[cH:11][cH:10]1)=[O:7].[NH2:8][NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][NH2:9])[cH:10][cH:11][c:12]1-[c:13]1[cH:14][n:15][c:16]([CH3:17])[o:18]1 | 0.594292 | C1CCOC1.COc1cc(C(=O)O)ccc1-c1cnc(C)o1.NN~O>>COc1cc(C(=O)NN)ccc1-c1cnc(C)o1 | C1CCOC1.COc1cc(C(=O)O)ccc1-c1cnc(C)o1.NN.O>>COc1cc(C(=O)NN)ccc1-c1cnc(C)o1 | US08822699B2_0745grants | 1a8ff08405eee030319262ef457b33ba6d021dd4531d7ad6db73601a | C1CCOC1.O.O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:12](-[c:13]2[cH:14][n:15][c:16]([CH3:17])[o:18]2)[cH:11][cH:10]1)=[O:7].[NH2:8][NH2:9] | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][NH2:9])[cH:10][cH:11][c:12]1-[c:13]1[cH:14][n:15][c:16]([CH3:17])[o:18]1 | ([N;D1;H2:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([N;D1;H2:4]-[NH2;D1;+0:5]) | ddcdb41d63c033d30ea62d6e50cd89d6bfca0813501037085964693f | 1 | 1 | C1CCOC1.O | 55 |
408,682 | 1,600,666 | null | [Cl:1][C:2]1[N:3]=[C:4]2[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[N:9][C:5]2=[N:6][C:7]=1Cl.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[NH4+].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]2[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[N:9][C:5]2=[N:6][C:7]=1[N:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]1 | |f:2.3| | US20140315888A1_0526 | 2,014 | ClCCl.Cl[c:6]1[n:7][c:8]2[n:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[n:16][c:17]1[Cl:18].[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:19][CH2:20]1.[Cl-].[NH4+]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]3[n:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]3[n:16][c:17]2[Cl:18])[CH2:19][CH2:20]1 | 0.896345 | CN1CCNCC1.ClCCl.Clc1cc2nc(Cl)c(Cl)nc2nc1Cl.[Cl-]~[NH4+]>>CN1CCN(c2nc3nc(Cl)c(Cl)cc3nc2Cl)CC1 | CN1CCNCC1.ClCCl.Clc1cc2nc(Cl)c(Cl)nc2nc1Cl.[Cl-].[NH4+]>>CN1CCN(c2nc3nc(Cl)c(Cl)cc3nc2Cl)CC1 | US20140315888A1_0526apps | b7d10e00e31535ab10eefac49d4ef039a6dd09e6a6b39e6c076d5740 | ClCCl.Cl[c:6]1[n:7][c:8]2[n:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[n:16][c:17]1[Cl:18].[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:19][CH2:20]1.[Cl-].[NH4+] | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]3[n:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]3[n:16][c:17]2[Cl:18])[CH2:19][CH2:20]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[#7;a:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 3dc06bda2af537840489d5b42deeb79863a93db85840f14ac98194e8 | 1 | 1 | ClCCl.[Cl-].[NH4+] | 505 |
342,672 | 353,662 | null | [N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14]=2[CH:31]=1)=[O:8])([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:14]=2[CH:31]=1)=[O:8] | null | US20060116383A1_0341 | 2,006 | CCO.O.O=[N+:29]([O-])[c:28]1[cH:27][cH:26][cH:25][c:24]([C:22]([NH:21][c:20]2[cH:19][cH:18][c:17]3[n:16][cH:15][n:14]([CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[c:32]3[cH:31]2)=[O:23])[cH:30]1.[NH4+].[Pd]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[n:14]1[cH:15][n:16][c:17]2[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[c:24]3[cH:25][cH:26][cH:27][c:28]([NH2:29])[cH:30]3)[cH:31][c:32]12 | 0.953094 | CCO.CCOC(=O)CC(c1ccccc1)n1cnc2ccc(NC(=O)c3cccc([N+](=O)[O-])c3)cc21.O.[NH4+].[Pd]>>CCOC(=O)CC(c1ccccc1)n1cnc2ccc(NC(=O)c3cccc(N)c3)cc21 | CCO.CCOC(=O)CC(c1ccccc1)n1cnc2ccc(NC(=O)c3cccc([N+](=O)[O-])c3)cc21.O.[NH4+].[Pd]>>CCOC(=O)CC(c1ccccc1)n1cnc2ccc(NC(=O)c3cccc(N)c3)cc21 | US20060116383A1_0341apps | 7298b462b8b123e583a229023b02f8f7d320c03c1a652c6a21523943 | CCO.O.O=[N+:29]([O-])[c:28]1[cH:27][cH:26][cH:25][c:24]([C:22]([NH:21][c:20]2[cH:19][cH:18][c:17]3[n:16][cH:15][n:14]([CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[c:32]3[cH:31]2)=[O:23])[cH:30]1.[NH4+].[Pd] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[n:14]1[cH:15][n:16][c:17]2[cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[c:24]3[cH:25][cH:26][cH:27][c:28]([NH2:29])[cH:30]3)[cH:31][c:32]12 | ([#7:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:5]:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:10]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C:7](-[#7:8])=[O;D1;H0:9]):[c:10]:1) | 66e5194ce0ee414ce7a56881d10c95e8776842432066942b97e318db | 1 | 1 | CCO.O.[NH4+].[Pd] | 489 |
135,114 | 490,410 | 826,021 | [NH2:1][C:2]1[C:3](=[O:30])[NH:4][C:5]2[C:10]([N:11]=1)=[C:9]([O:12][C:13]1[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:16]=[C:15](Cl)[N:14]=1)[CH:8]=[CH:7][CH:6]=2.[NH2:31][CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][N:34]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>>[NH2:1][C:2]1[C:3](=[O:30])[NH:4][C:5]2[C:10]([N:11]=1)=[C:9]([O:12][C:13]1[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:16]=[C:15]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][N:34]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:14]=1)[CH:8]=[CH:7][CH:6]=2 | null | US07335672B2_0354 | 2,008 | Cl[c:16]1[n:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][c:24]3[nH:25][c:26](=[O:27])[c:28]([NH2:29])[n:30][c:31]23)[cH:32][c:33](-[c:34]2[cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]2)[n:44]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][NH2:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][NH:15][c:16]1[n:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][c:24]3[nH:25][c:26](=[O:27])[c:28]([NH2:29])[n:30][c:31]23)[cH:32][c:33](-[c:34]2[cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]2)[n:44]1 | 0.11491 | CC(C)(C)OC(=O)N1CCCCC1CN.Nc1nc2c(Oc3cc(-c4ccc(C(F)(F)F)cc4)nc(Cl)n3)cccc2[nH]c1=O>>CC(C)(C)OC(=O)N1CCCCC1CNc1nc(Oc2cccc3[nH]c(=O)c(N)nc23)cc(-c2ccc(C(F)(F)F)cc2)n1 | CC(C)(C)OC(=O)N1CCCCC1CN.Nc1nc2c(Oc3cc(-c4ccc(C(F)(F)F)cc4)nc(Cl)n3)cccc2[nH]c1=O>>CC(C)(C)OC(=O)N1CCCCC1CNc1nc(Oc2cccc3[nH]c(=O)c(N)nc23)cc(-c2ccc(C(F)(F)F)cc2)n1 | US07335672B2_0354grants | 4f24d6f340ae9f79af1d7de1d24cffb8c7b2ff0bc0de2b89bdf63b1e | Cl[c:16]1[n:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][c:24]3[nH:25][c:26](=[O:27])[c:28]([NH2:29])[n:30][c:31]23)[cH:32][c:33](-[c:34]2[cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]2)[n:44]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][NH2:15] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][NH:15][c:16]1[n:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][c:24]3[nH:25][c:26](=[O:27])[c:28]([NH2:29])[n:30][c:31]23)[cH:32][c:33](-[c:34]2[cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]2)[n:44]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH2;D1;+0:5]) | 37356f3ff9da6e71c10e8b10fe57838cb502f1ab49d9cb2b73931baa | 1 | 1 | null | 544 |
28,729 | 132,912 | 214,279 | [O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([Cl:16])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1 | null | US04937246_ | 1,990 | O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2.c1ccccc1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2 | 0.563654 | O=C(O)c1ccc2c(c1)OCCO2.O=S(Cl)Cl.c1ccccc1>>O=C(Cl)c1ccc2c(c1)OCCO2 | O=C(O)c1ccc2c(c1)OCCO2.O=S(Cl)Cl.c1ccccc1>>O=C(Cl)c1ccc2c(c1)OCCO2 | US04937246_grants | 1a1cd14caa099148e944b796e134d85d62f9fce8792a33245a4dcdeb | O=S(Cl)[Cl:3].O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2.c1ccccc1 | [O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][CH2:12][O:13]2 | ([Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]) | b71280db4b70d661700213321895a7af48fe382569269c0e754a4f84 | 1 | 1 | c1ccccc1 | 3 |
105,997 | 403,524 | 689,198 | [Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([F:21])[CH:14]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:22].B(Br)(Br)Br>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:21])[CH:14]=3)=[CH:9][C:10]=2[F:12])[CH:5]=[CH:4][C:3]=1[OH:22] | null | US06914074B2_0371 | 2,005 | BrB(Br)Br.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]3[c:11]([Cl:12])[c:13]([OH:14])[cH:15][cH:16][c:17]3[cH:18]2)[cH:19][c:20]1[F:21]>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]3[c:11]([Cl:12])[c:13]([OH:14])[cH:15][cH:16][c:17]3[cH:18]2)[cH:19][c:20]1[F:21] | 0.992264 | BrB(Br)Br.COc1ccc(-c2cc(F)c3c(Cl)c(O)ccc3c2)cc1F>>Oc1ccc(-c2cc(F)c3c(Cl)c(O)ccc3c2)cc1F | BrB(Br)Br.COc1ccc(-c2cc(F)c3c(Cl)c(O)ccc3c2)cc1F>>Oc1ccc(-c2cc(F)c3c(Cl)c(O)ccc3c2)cc1F | US06914074B2_0371grants | d73387eb3c4cc1dceae80629e4f151ec61c9e47dd5df42f698ac1813 | BrB(Br)Br.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]3[c:11]([Cl:12])[c:13]([OH:14])[cH:15][cH:16][c:17]3[cH:18]2)[cH:19][c:20]1[F:21] | [OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[c:10]3[c:11]([Cl:12])[c:13]([OH:14])[cH:15][cH:16][c:17]3[cH:18]2)[cH:19][c:20]1[F:21] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 0.5 | 2 | BrB(Br)Br | 48 |
294,453 | 958,406 | 1,612,098 | [NH2:1][C@@H:2]([CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.F[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=1[N+:40]([O-:42])=[O:41]>CN(C=O)C.CCOC(C)=O>[O:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][C@@H:2]([NH:1][C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=2[N+:40]([O-:42])=[O:41])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:8]1 | null | US09018381B2_0934 | 2,015 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.F[c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:32][c:28]1[N+:29](=[O:30])[O-:31].[NH2:9][C@@H:10]([CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][C:20](=[O:21])[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C@@H:10]([CH2:11][S:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C:20](=[O:21])[N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[c:28]([N+:29](=[O:30])[O-:31])[cH:32]1 | 0.479619 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.NS(=O)(=O)c1ccc(F)c([N+](=O)[O-])c1.N[C@@H](CSc1ccccc1)CC(=O)N1CCOCC1>>NS(=O)(=O)c1ccc(N[C@@H](CSc2ccccc2)CC(=O)N2CCOCC2)c([N+](=O)[O-])c1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.NS(=O)(=O)c1ccc(F)c([N+](=O)[O-])c1.N[C@@H](CSc1ccccc1)CC(=O)N1CCOCC1>>NS(=O)(=O)c1ccc(N[C@@H](CSc2ccccc2)CC(=O)N2CCOCC2)c([N+](=O)[O-])c1 | US09018381B2_0934grants | 0237434609c1ccb3fa0e69bec7db945ec6cbb591baac5469ee9f9e6c | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.F[c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:32][c:28]1[N+:29](=[O:30])[O-:31].[NH2:9][C@@H:10]([CH2:11][S:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][C:20](=[O:21])[N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][C@@H:10]([CH2:11][S:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C:20](=[O:21])[N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[c:28]([N+:29](=[O:30])[O-:31])[cH:32]1 | ([C:4]-[NH;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[NH2;D1;+0:5]) | f6efd7b393383415221f79c2bd878580bac11ebc7094d039a036f219 | 1 | 1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O | 572 |
103,326 | 395,259 | 675,349 | [N:1]([CH2:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[O:9][C:10]=1[CH3:11])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[O:9][C:10]([CH3:11])=[C:6]([CH2:5][CH2:4][NH2:1])[N:7]=2)=[CH:13][CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1 | null | US06861440B2_00588 | 2,005 | C1CCOC1.O.[N-]=[N+]=[N:23][CH2:22][CH2:21][c:20]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19][c:20]1[CH2:21][CH2:22][NH2:23] | 0.884362 | C1CCOC1.Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCN=[N+]=[N-].O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCN | C1CCOC1.Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCN=[N+]=[N-].O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Cc1oc(-c2ccc(OCc3ccccc3)cc2)nc1CCN | US06861440B2_00588grants | 878712c4653a6f812ec2783a4bbc32a64247f59f974695e77ae6f9a8 | C1CCOC1.O.[N-]=[N+]=[N:23][CH2:22][CH2:21][c:20]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[n:19][c:20]1[CH2:21][CH2:22][NH2:23] | ([C:1]-[NH2;D1;+0:2])>>([C:1]-[N;H0;D2;+0:2]=[N+]=[N-]) | 070a946412681dc3cde4c63e0e9dd945476d44bb1aa5127f721cc5fd | 1 | 1 | C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 89 |
10,817 | 54,800 | 88,676 | Cl[C:2]1[C:3](=[O:19])[N:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.O>C(O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=[C:2]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:3]2=[O:19])=[CH:13][CH:14]=1 | null | US04296114_ | 1,981 | CCN(CC)CC.CCO.Cl[c:3]1[c:2](=[O:1])[n:17](-[c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:16]2[c:11]([n:10]1)[cH:12][cH:13][cH:14][cH:15]2.O.[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[O:1]=[c:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1-[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1 | 0.687076 | C1CCNCC1.CCN(CC)CC.CCO.O.O=c1c(Cl)nc2ccccc2n1-c1ccc(Cl)cc1>>O=c1c(N2CCCCC2)nc2ccccc2n1-c1ccc(Cl)cc1 | C1CCNCC1.CCN(CC)CC.CCO.O.O=c1c(Cl)nc2ccccc2n1-c1ccc(Cl)cc1>>O=c1c(N2CCCCC2)nc2ccccc2n1-c1ccc(Cl)cc1 | US04296114_grants | ad190324ba80b08d89e71853b51cf56aff58889aa1633170b064c467 | CCN(CC)CC.CCO.Cl[c:3]1[c:2](=[O:1])[n:17](-[c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:16]2[c:11]([n:10]1)[cH:12][cH:13][cH:14][cH:15]2.O.[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1 | [O:1]=[c:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1-[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3]:[#7;a:4])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 3dc06bda2af537840489d5b42deeb79863a93db85840f14ac98194e8 | 1 | 1 | CCN(CC)CC.CCO.O | 505 |
394,736 | 1,248,692 | null | [F:1][C:2]([F:34])([F:33])[C:3]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:4]=1[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:13](/[CH:16]=[C:17]2/[C:18]([NH:23][CH3:24])=[N:19][C:20](=[O:22])[S:21]/2)=[CH:12][C:8]=1C(O)=O.CN.O1CCCC1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C[N:65]([CH3:68])[CH:66]=[O:67]>O>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[CH:25][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[CH:12][C:13](/[CH:16]=[C:17]2/[C:18]([NH:23][CH3:24])=[N:19][C:20](=[O:22])[S:21]/2)=[CH:14][C:15]=1[C:66]([NH:65][CH3:68])=[O:67] | |f:1.2,4.5| | US20120196864A1_1123 | 2,012 | C1CCOC1.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O[C:3](=[O:4])[c:5]1[cH:6][c:7](/[CH:8]=[C:9]2\[S:10][C:11](=[O:12])[N:13]=[C:14]2[NH:15][CH3:16])[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]1[C:32]([F:33])([F:34])[F:35].On1nnc2ccccc21.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](/[CH:8]=[C:9]2\[S:10][C:11](=[O:12])[N:13]=[C:14]2[NH:15][CH3:16])[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]1[C:32]([F:33])([F:34])[F:35] | 0.081107 | C1CCOC1~CN.CCN=C=NCCCN(C)C~Cl.CN(C)C=O.CNC1=NC(=O)S/C1=C\c1ccc(OCc2ccc(C(F)(F)F)cc2C(F)(F)F)c(C(=O)O)c1.O.On1nnc2ccccc21>>CNC(=O)c1cc(/C=C2\SC(=O)N=C2NC)ccc1OCc1ccc(C(F)(F)F)cc1C(F)(F)F | C1CCOC1.CCN=C=NCCCN(C)C.CN.CN(C)C=O.CNC1=NC(=O)S/C1=C\c1ccc(OCc2ccc(C(F)(F)F)cc2C(F)(F)F)c(C(=O)O)c1.Cl.O.On1nnc2ccccc21>>CNC(=O)c1cc(/C=C2\SC(=O)N=C2NC)ccc1OCc1ccc(C(F)(F)F)cc1C(F)(F)F | US20120196864A1_1123apps | 6294e171932b4cd9e15f80662db9a9891d386341780831e917642ada | C1CCOC1.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.O[C:3](=[O:4])[c:5]1[cH:6][c:7](/[CH:8]=[C:9]2\[S:10][C:11](=[O:12])[N:13]=[C:14]2[NH:15][CH3:16])[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]1[C:32]([F:33])([F:34])[F:35].On1nnc2ccccc21.[CH3:1][NH2:2] | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](/[CH:8]=[C:9]2\[S:10][C:11](=[O:12])[N:13]=[C:14]2[NH:15][CH3:16])[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]1[C:32]([F:33])([F:34])[F:35] | ([C;D1;H3:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C;D1;H3:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | C1CCOC1.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O.On1nnc2ccccc21 | 334 |
274,223 | 899,429 | 1,500,326 | [C:1]([C:3]1[CH:4]=[C:5]([N+:15]([O-:17])=[O:16])[C:6]([C:12]([OH:14])=O)=[N:7][C:8]=1[O:9][CH2:10][CH3:11])#[N:2].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.Cl.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:50]1[S:51][C:52]([CH2:55][N:56]2[CH2:61][CH2:60][CH:59]([CH2:62][NH2:63])[CH2:58][CH2:57]2)=[CH:53][N:54]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[C:5]([N+:15]([O-:17])=[O:16])[C:6]([C:12]([NH:63][CH2:62][CH:59]2[CH2:60][CH2:61][N:56]([CH2:55][C:52]3[S:51][C:50]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=4)=[N:54][CH:53]=3)[CH2:57][CH2:58]2)=[O:14])=[N:7][C:8]=1[O:9][CH2:10][CH3:11])#[N:2] | |f:1.2,3.4,5.6.7.8| | US08809538B2_2420 | 2,014 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.Cl.Cl.O.O.O[C:7]([c:6]1[n:5][c:4]([O:3][CH2:2][CH3:1])[c:34]([C:35]#[N:36])[cH:33][c:29]1[N+:30](=[O:31])[O-:32])=[O:8].On1nnc2ccccc21.[NH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][n:25]3)[s:26]2)[CH2:27][CH2:28]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][n:18][c:19](-[c:20]4[cH:21][cH:22][cH:23][cH:24][n:25]4)[s:26]3)[CH2:27][CH2:28]2)[c:29]([N+:30](=[O:31])[O-:32])[cH:33][c:34]1[C:35]#[N:36] | 0.92223 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C~Cl.CCOc1nc(C(=O)O)c([N+](=O)[O-])cc1C#N.CN(C)C=O.Cl~Cl~Cl~NCC1CCN(Cc2cnc(-c3ccccn3)s2)CC1.O.O~On1nnc2ccccc21>>CCOc1nc(C(=O)NCC2CCN(Cc3cnc(-c4ccccn4)s3)CC2)c([N+](=O)[O-])cc1C#N | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOc1nc(C(=O)O)c([N+](=O)[O-])cc1C#N.CN(C)C=O.Cl.Cl.Cl.Cl.NCC1CCN(Cc2cnc(-c3ccccn3)s2)CC1.O.O.On1nnc2ccccc21>>CCOc1nc(C(=O)NCC2CCN(Cc3cnc(-c4ccccn4)s3)CC2)c([N+](=O)[O-])cc1C#N | US08809538B2_2420grants | f089b3879a08ca5b9fbe4215bc2880d47a1393299c26688377c63322 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.Cl.Cl.O.O.O[C:7]([c:6]1[n:5][c:4]([O:3][CH2:2][CH3:1])[c:34]([C:35]#[N:36])[cH:33][c:29]1[N+:30](=[O:31])[O-:32])=[O:8].On1nnc2ccccc21.[NH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][n:25]3)[s:26]2)[CH2:27][CH2:28]1 | [CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([C:7](=[O:8])[NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][n:18][c:19](-[c:20]4[cH:21][cH:22][cH:23][cH:24][n:25]4)[s:26]3)[CH2:27][CH2:28]2)[c:29]([N+:30](=[O:31])[O-:32])[cH:33][c:34]1[C:35]#[N:36] | ([#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]).([C:5]-[NH2;D1;+0:6]) | e83ee81602b397ed833d633e817ffa090f0d21c621887dacaf746f5e | 1 | 1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.Cl.Cl.O.O.On1nnc2ccccc21 | 137 |
121,484 | 450,018 | 764,306 | CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.[Cl:39][C:40]1[C:41]([C:50]([F:53])([F:52])[F:51])=[N:42][N:43]([CH2:46][C:47](O)=[O:48])[C:44]=1[CH3:45]>>[Cl:39][C:40]1[C:41]([C:50]([F:52])([F:51])[F:53])=[N:42][N:43]([CH2:46][C:47]([N:36]2[CH2:37][CH2:38][N:33]([C:30]3[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=3)[CH2:34][CH2:35]2)=[O:48])[C:44]=1[CH3:45] | |f:0.1| | US07157464B2_0369 | 2,007 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:11](=[O:12])[CH2:13][n:14]1[n:15][c:16]([C:17]([F:18])([F:19])[F:20])[c:21]([Cl:22])[c:23]1[CH3:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][n:14]3[n:15][c:16]([C:17]([F:18])([F:19])[F:20])[c:21]([Cl:22])[c:23]3[CH3:24])[CH2:25][CH2:26]2)[cH:27][cH:28]1 | 0.289396 | CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.COc1ccc(N2CCNCC2)cc1.Cc1c(Cl)c(C(F)(F)F)nn1CC(=O)O>>COc1ccc(N2CCN(C(=O)Cn3nc(C(F)(F)F)c(Cl)c3C)CC2)cc1 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.COc1ccc(N2CCNCC2)cc1.Cc1c(Cl)c(C(F)(F)F)nn1CC(=O)O.F[P-](F)(F)(F)(F)F>>COc1ccc(N2CCN(C(=O)Cn3nc(C(F)(F)F)c(Cl)c3C)CC2)cc1 | US07157464B2_0369grants | 3cfc43796f8c14cb379a7e495f6a9f50a44bcc2b203c5978915e2ad8 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:11](=[O:12])[CH2:13][n:14]1[n:15][c:16]([C:17]([F:18])([F:19])[F:20])[c:21]([Cl:22])[c:23]1[CH3:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:25][CH2:26]2)[cH:27][cH:28]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH2:13][n:14]3[n:15][c:16]([C:17]([F:18])([F:19])[F:20])[c:21]([Cl:22])[c:23]3[CH3:24])[CH2:25][CH2:26]2)[cH:27][cH:28]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | 146 |
242,360 | 807,187 | 1,336,654 | [CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10](C3N4C(C=NC(SC)=N4)=CC=3)[CH:11]=[CH:12][CH:13]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.BrC1C=CC=C(S(CC2CC2)(=O)=O)C=1.CC([O-])=O.[K+].[CH3:44][C:45]1([CH3:61])[C:49]([CH3:51])([CH3:50])[O:48][B:47]([B:47]2[O:48][C:49]([CH3:51])([CH3:50])[C:45]([CH3:61])([CH3:44])[O:46]2)[O:46]1.ClCCl>CN(C)C=O>[CH:1]1([CH2:4][S:5]([C:8]2[CH:9]=[C:10]([B:47]3[O:48][C:49]([CH3:51])([CH3:50])[C:45]([CH3:61])([CH3:44])[O:46]3)[CH:11]=[CH:12][CH:13]=2)(=[O:6])=[O:7])[CH2:2][CH2:3]1 | |f:2.3| | US08471005B2_2222 | 2,013 | Br[c:6]1[cH:7][cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH2:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]2)OC1(C)C.CN(C)C=O.CSc1ncc2ccc(-c3cccc(S(=O)(=O)CC4CC4)c3)n2n1.ClCCl.[K+]>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH2:14][CH:15]3[CH2:16][CH2:17]3)[cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22] | 0.087904 | CC(=O)[O-]~[K+].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CN(C)C=O.CSc1ncc2ccc(-c3cccc(S(=O)(=O)CC4CC4)c3)n2n1.ClCCl.O=S(=O)(CC1CC1)c1cccc(Br)c1>>CC1(C)OB(c2cccc(S(=O)(=O)CC3CC3)c2)OC1(C)C | CC(=O)[O-].CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CN(C)C=O.CSc1ncc2ccc(-c3cccc(S(=O)(=O)CC4CC4)c3)n2n1.ClCCl.O=S(=O)(CC1CC1)c1cccc(Br)c1.[K+]>>CC1(C)OB(c2cccc(S(=O)(=O)CC3CC3)c2)OC1(C)C | US08471005B2_2222grants | 759dede56b0d0a941cc06cee1bdd1acbe734866a8806944c9a541527 | Br[c:6]1[cH:7][cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH2:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1.CC(=O)[O-].CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]2)OC1(C)C.CN(C)C=O.CSc1ncc2ccc(-c3cccc(S(=O)(=O)CC4CC4)c3)n2n1.ClCCl.[K+] | [CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[CH2:14][CH:15]3[CH2:16][CH2:17]3)[cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22] | ([#8:5]-[B;H0;D3;+0:4](-[#8:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[B;H0;D3;+0:4](-[#8:5])-[#8:6])-O-C-1(-C)-C) | 809111b01e38b549ab34d8fc095aeb8c0540db06f3c41a247745e882 | 1 | 1 | CC(=O)[O-].CN(C)C=O.CSc1ncc2ccc(-c3cccc(S(=O)(=O)CC4CC4)c3)n2n1.ClCCl.[K+] | 942 |
227,725 | 763,091 | 1,257,652 | [NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:28][CH2:27]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:32](Cl)(=[O:34])[CH3:33].C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[C:32]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:27][CH2:28]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:34])[CH3:33] | null | US08324395B2_1121 | 2,012 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.Cl[C:2]([CH3:1])=[O:3].O.[NH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]5([C:26]#[N:27])[CH2:28][CH2:29]5)[cH:30]4)[cH:31]3)[cH:32][c:33]2[s:34]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]5([C:26]#[N:27])[CH2:28][CH2:29]5)[cH:30]4)[cH:31]3)[cH:32][c:33]2[s:34]1 | 0.722945 | C1CCOC1.CC(=O)Cl.CCN(CC)CC.CCOC(C)=O.N#CC1(c2cccc(C(=O)Nc3cccc(Oc4ccc5nc(N)sc5c4)c3)c2)CC1.O>>CC(=O)Nc1nc2ccc(Oc3cccc(NC(=O)c4cccc(C5(C#N)CC5)c4)c3)cc2s1 | C1CCOC1.CC(=O)Cl.CCN(CC)CC.CCOC(C)=O.N#CC1(c2cccc(C(=O)Nc3cccc(Oc4ccc5nc(N)sc5c4)c3)c2)CC1.O>>CC(=O)Nc1nc2ccc(Oc3cccc(NC(=O)c4cccc(C5(C#N)CC5)c4)c3)cc2s1 | US08324395B2_1121grants | 2895089aa939ce084c8455371cd4e50cbb4eee65c103ff66c98c95d1 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.Cl[C:2]([CH3:1])=[O:3].O.[NH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]5([C:26]#[N:27])[CH2:28][CH2:29]5)[cH:30]4)[cH:31]3)[cH:32][c:33]2[s:34]1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[c:20]4[cH:21][cH:22][cH:23][c:24]([C:25]5([C:26]#[N:27])[CH2:28][CH2:29]5)[cH:30]4)[cH:31]3)[cH:32][c:33]2[s:34]1 | ([#16;a:4]:[c:5](:[#7;a:6])-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([#16;a:4]:[c:5](:[#7;a:6])-[NH2;D1;+0:7]) | fb0e611d9aa0d97d0fa7ba32c78621db605b5592c522863c5957a0dd | 1 | 1 | C1CCOC1.CCN(CC)CC.CCOC(C)=O.O | 553 |
337,611 | 248,420 | null | [Cl:1][C:2]1[C:3]([O:31][CH2:32][CH3:33])=[C:4](/[C:17](/[CH3:30])=[C:18](/[F:29])\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[C:23]([O:25]CC)=[O:24])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:13])([CH3:12])[CH:8]=[C:7]2[CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[C:3]([O:31][CH2:32][CH3:33])=[C:4](/[C:17](/[CH3:30])=[C:18](/[F:29])\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[C:23]([OH:25])=[O:24])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:12])([CH3:13])[CH:8]=[C:7]2[CH:14]([CH3:15])[CH3:16] | |f:1.2| | US20050096380A1_0396 | 2,005 | C1CCOC1.CCO.CC[O:17][C:15](/[CH:14]=[C:12](/[CH:11]=[CH:10]/[C:8](=[C:6](\[c:5]1[c:4]([O:3][CH2:2][CH3:1])[c:21]([Cl:22])[c:20]2[c:19]([cH:18]1)[C:28]([CH:29]([CH3:30])[CH3:31])=[CH:27][C:24]([CH3:25])([CH3:26])[O:23]2)[CH3:7])[F:9])[CH3:13])=[O:16].[Na+].[OH-]>>[CH3:1][CH2:2][O:3][c:4]1[c:5](/[C:6]([CH3:7])=[C:8]([F:9])\[CH:10]=[CH:11]\[C:12]([CH3:13])=[CH:14]\[C:15](=[O:16])[OH:17])[cH:18][c:19]2[c:20]([c:21]1[Cl:22])[O:23][C:24]([CH3:25])([CH3:26])[CH:27]=[C:28]2[CH:29]([CH3:30])[CH3:31] | 0.613644 | C1CCOC1.CCO.CCOC(=O)/C=C(C)/C=C/C(F)=C(/C)c1cc2c(c(Cl)c1OCC)OC(C)(C)C=C2C(C)C.[Na+]~[OH-]>>CCOc1c(/C(C)=C(F)\C=C\C(C)=C\C(=O)O)cc2c(c1Cl)OC(C)(C)C=C2C(C)C | C1CCOC1.CCO.CCOC(=O)/C=C(C)/C=C/C(F)=C(/C)c1cc2c(c(Cl)c1OCC)OC(C)(C)C=C2C(C)C.[Na+].[OH-]>>CCOc1c(/C(C)=C(F)\C=C\C(C)=C\C(=O)O)cc2c(c1Cl)OC(C)(C)C=C2C(C)C | US20050096380A1_0396apps | fc399ba20b7a63cadc1324a1c43a9d89805086b586370c5c85599987 | C1CCOC1.CCO.CC[O:17][C:15](/[CH:14]=[C:12](/[CH:11]=[CH:10]/[C:8](=[C:6](\[c:5]1[c:4]([O:3][CH2:2][CH3:1])[c:21]([Cl:22])[c:20]2[c:19]([cH:18]1)[C:28]([CH:29]([CH3:30])[CH3:31])=[CH:27][C:24]([CH3:25])([CH3:26])[O:23]2)[CH3:7])[F:9])[CH3:13])=[O:16].[Na+].[OH-] | [CH3:1][CH2:2][O:3][c:4]1[c:5](/[C:6]([CH3:7])=[C:8]([F:9])\[CH:10]=[CH:11]\[C:12]([CH3:13])=[CH:14]\[C:15](=[O:16])[OH:17])[cH:18][c:19]2[c:20]([c:21]1[Cl:22])[O:23][C:24]([CH3:25])([CH3:26])[CH:27]=[C:28]2[CH:29]([CH3:30])[CH3:31] | ([C:5]=[C:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]) | f7700dd7b87e14473011f502e59081e27e0a155719b46e62ad2ee91c | 1 | 1 | C1CCOC1.CCO.[Na+].[OH-] | 122 |
122,678 | 453,383 | 769,122 | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:36])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=4)[C:16]([CH:33]=[O:34])=[C:15]3[CH3:35])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:36])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:29])([F:30])[F:31])[C:24]([F:25])([F:26])[F:27])=[CH:20][CH:21]=4)[C:16]([CH2:33][OH:34])=[C:15]3[CH3:35])[N:12]=2)[CH:5]=[CH:6][CH:7]=1 | |f:1.2.3.4.5.6| | US07173048B2_0478 | 2,007 | C1CCOC1.CCOCC.O.[Al+3].[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[n:12][c:13]1[CH2:14][n:15]1[c:16]([CH3:17])[c:18]([CH:19]=[O:20])[c:21]2[cH:22][c:23]([C:24]([OH:25])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[cH:34][cH:35][c:36]12.[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[n:12][c:13]1[CH2:14][n:15]1[c:16]([CH3:17])[c:18]([CH2:19][OH:20])[c:21]2[cH:22][c:23]([C:24]([OH:25])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[cH:34][cH:35][c:36]12 | 0.090455 | C1CCOC1.CCOCC.Cc1oc(-c2cccc(Cl)c2)nc1Cn1c(C)c(C=O)c2cc(C(O)(C(F)(F)F)C(F)(F)F)ccc21.O.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>Cc1oc(-c2cccc(Cl)c2)nc1Cn1c(C)c(CO)c2cc(C(O)(C(F)(F)F)C(F)(F)F)ccc21 | C1CCOC1.CCOCC.Cc1oc(-c2cccc(Cl)c2)nc1Cn1c(C)c(C=O)c2cc(C(O)(C(F)(F)F)C(F)(F)F)ccc21.O.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>Cc1oc(-c2cccc(Cl)c2)nc1Cn1c(C)c(CO)c2cc(C(O)(C(F)(F)F)C(F)(F)F)ccc21 | US07173048B2_0478grants | d1a682111d2559a894a7fe45dfba99afc68ccb72d1339c5a2a85e0c0 | C1CCOC1.CCOCC.O.[Al+3].[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[n:12][c:13]1[CH2:14][n:15]1[c:16]([CH3:17])[c:18]([CH:19]=[O:20])[c:21]2[cH:22][c:23]([C:24]([OH:25])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[cH:34][cH:35][c:36]12.[H-].[H-].[H-].[H-].[Li+] | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]2)[n:12][c:13]1[CH2:14][n:15]1[c:16]([CH3:17])[c:18]([CH2:19][OH:20])[c:21]2[cH:22][c:23]([C:24]([OH:25])([C:26]([F:27])([F:28])[F:29])[C:30]([F:31])([F:32])[F:33])[cH:34][cH:35][c:36]12 | ([#7;a:1]:[c:2]:[c:3]-[CH2;D2;+0:4]-[OH;D1;+0:5])>>([#7;a:1]:[c:2]:[c:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5]) | 61bd12dc96937cc6540f0277c1c3f3e429f86c2732c07c6846f236b1 | 1 | 1 | C1CCOC1.CCOCC.O.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 476 |
153,454 | 546,648 | 914,879 | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[CH:18][NH:17][N:16]=2)[N:3]=1.[F:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[C:25]([F:27])[CH:26]=1>>[F:20][C:21]1[CH:22]=[C:23]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[CH:5]=[C:4]([NH:14][C:15]3[CH:19]=[CH:18][NH:17][N:16]=3)[N:3]=2)[CH:24]=[C:25]([F:27])[CH:26]=1 | null | US07572809B2_1585 | 2,009 | Cl[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][c:25]2[cH:24][c:17]([NH:18][c:19]2[cH:20][cH:21][nH:22][n:23]2)[n:16]1.OB(O)[c:8]1[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][nH:22][n:23]3)[cH:24][c:25]2[cH:26]1 | 0.84735 | COc1ccc2c(Cl)nc(Nc3cc[nH]n3)cc2c1.OB(O)c1cc(F)cc(F)c1>>COc1ccc2c(-c3cc(F)cc(F)c3)nc(Nc3cc[nH]n3)cc2c1 | COc1ccc2c(Cl)nc(Nc3cc[nH]n3)cc2c1.OB(O)c1cc(F)cc(F)c1>>COc1ccc2c(-c3cc(F)cc(F)c3)nc(Nc3cc[nH]n3)cc2c1 | US07572809B2_1585grants | 5f995783e14671b8b156003e7fb672e196c997a0340893a9bcabdb2d | Cl[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][c:25]2[cH:24][c:17]([NH:18][c:19]2[cH:20][cH:21][nH:22][n:23]2)[n:16]1.OB(O)[c:8]1[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[cH:9][c:10]([F:11])[cH:12][c:13]([F:14])[cH:15]3)[n:16][c:17]([NH:18][c:19]3[cH:20][cH:21][nH:22][n:23]3)[cH:24][c:25]2[cH:26]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[c;H0;D3;+0:4](:[c:5]):[c:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 631db43ddca950490e6cbcb52cbca1879bbed13f087c1f676032508b | 1 | 1 | null | 865 |
245,910 | 817,915 | 1,353,530 | [F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17](=[O:19])[CH2:18][CH:13]2[CH2:12]1.[CH2:20](O)[CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH:14]2[CH2:16][C:17]3([CH2:18][CH:13]2[CH2:12]1)[O:22][CH2:21][CH2:20][O:19]3 | |f:2.3| | US08507540B2_0173 | 2,013 | Cc1ccc(S(=O)(=O)O)cc1.O.O[CH2:17][CH2:18][OH:19].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH:10]3[CH2:11][C:12](=[O:16])[CH2:13][CH:14]3[CH2:15]2)[c:20]([F:21])[cH:22]1.c1ccccc1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH:10]3[CH2:11][C:12]4([CH2:13][CH:14]3[CH2:15]2)[O:16][CH2:17][CH2:18][O:19]4)[c:20]([F:21])[cH:22]1 | 0.363272 | Cc1ccc(S(=O)(=O)O)cc1~O.O=C1CC2CN(c3ccc([N+](=O)[O-])cc3F)CC2C1.OCCO.c1ccccc1>>O=[N+]([O-])c1ccc(N2CC3CC4(CC3C2)OCCO4)c(F)c1 | Cc1ccc(S(=O)(=O)O)cc1.O.O=C1CC2CN(c3ccc([N+](=O)[O-])cc3F)CC2C1.OCCO.c1ccccc1>>O=[N+]([O-])c1ccc(N2CC3CC4(CC3C2)OCCO4)c(F)c1 | US08507540B2_0173grants | b2c9c791526ab259fcd11b9ce12ef05461131b8bedf79f1d4decee69 | Cc1ccc(S(=O)(=O)O)cc1.O.O[CH2:17][CH2:18][OH:19].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH:10]3[CH2:11][C:12](=[O:16])[CH2:13][CH:14]3[CH2:15]2)[c:20]([F:21])[cH:22]1.c1ccccc1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH:10]3[CH2:11][C:12]4([CH2:13][CH:14]3[CH2:15]2)[O:16][CH2:17][CH2:18][O:19]4)[c:20]([F:21])[cH:22]1 | ([C:4]-[C;H0;D4;+0:5]1(-[C:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1)>>(O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3]).([C:4]-[C;H0;D3;+0:5](-[C:6])=[O;H0;D1;+0:7]) | e4a5e247248b212ffa5f297acaa21d528da5e85cae1a0e49a41decf5 | 1 | 1 | Cc1ccc(S(=O)(=O)O)cc1.O.c1ccccc1 | 265 |
320,989 | 1,043,346 | 1,769,420 | [C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([C:27]([N:30]5[C@H:35]([CH3:36])[CH2:34][CH2:33][CH2:32][C@@H:31]5[CH3:37])=[N:28][N:29]=4)[CH:26]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:38]2[CH:39]=[N:40][N:41]([CH2:43][CH2:44][OH:45])[CH:42]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:46][S:47](Cl)(=[O:49])=[O:48].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]4[N:25]([C:27]([N:30]5[C@H:31]([CH3:37])[CH2:32][CH2:33][CH2:34][C@@H:35]5[CH3:36])=[N:28][N:29]=4)[CH:26]=3)[CH2:16][CH2:15]2)=[O:12])[N:7]([C:38]2[CH:39]=[N:40][N:41]([CH2:43][CH2:44][O:45][S:47]([CH3:46])(=[O:49])=[O:48])[CH:42]=2)[N:6]=1)([CH3:3])([CH3:4])[CH3:2] | null | US09359354B2_0647 | 2,016 | CCN(C(C)C)C(C)C.ClCCl.Cl[S:41]([CH3:42])(=[O:43])=[O:44].[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][n:37]([CH2:38][CH2:39][OH:40])[cH:45]4)[CH2:46][CH2:47]3)[cH:48][n:49]12>>[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][n:37]([CH2:38][CH2:39][O:40][S:41]([CH3:42])(=[O:43])=[O:44])[cH:45]4)[CH2:46][CH2:47]3)[cH:48][n:49]12 | 0.267607 | CCN(C(C)C)C(C)C.CS(=O)(=O)Cl.C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(OC3CCC(NC(=O)Nc4cc(C(C)(C)C)nn4-c4cnn(CCO)c4)CC3)cn12.ClCCl>>C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(OC3CCC(NC(=O)Nc4cc(C(C)(C)C)nn4-c4cnn(CCOS(C)(=O)=O)c4)CC3)cn12 | CCN(C(C)C)C(C)C.CS(=O)(=O)Cl.C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(OC3CCC(NC(=O)Nc4cc(C(C)(C)C)nn4-c4cnn(CCO)c4)CC3)cn12.ClCCl>>C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(OC3CCC(NC(=O)Nc4cc(C(C)(C)C)nn4-c4cnn(CCOS(C)(=O)=O)c4)CC3)cn12 | US09359354B2_0647grants | afc5b47286a586b9153c38d8e535d9a6572a922751408541f2f62080 | CCN(C(C)C)C(C)C.ClCCl.Cl[S:41]([CH3:42])(=[O:43])=[O:44].[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][n:37]([CH2:38][CH2:39][OH:40])[cH:45]4)[CH2:46][CH2:47]3)[cH:48][n:49]12 | [CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][n:37]([CH2:38][CH2:39][O:40][S:41]([CH3:42])(=[O:43])=[O:44])[cH:45]4)[CH2:46][CH2:47]3)[cH:48][n:49]12 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 0 |
138,551 | 501,222 | 842,456 | C[O:2][C:3](=O)[C@@H:4]1[C@@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:7][CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:20]([O:19][C:17]([N:5]1[CH2:6][CH2:7][C@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[C@H:4]1[CH2:3][OH:2])=[O:18])([CH3:23])([CH3:22])[CH3:21] | |f:1.2| | US07388027B2_0219 | 2,008 | C1CCOC1.CC[BH-](CC)CC.CO[C:21]([C@H:20]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][C@@H:11]1[O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22].[Li+]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[C@H:20]1[CH2:21][OH:22] | 0.076424 | C1CCOC1.CC[BH-](CC)CC~[Li+].COC(=O)[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO | C1CCOC1.CC[BH-](CC)CC.COC(=O)[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CCN1C(=O)OC(C)(C)C.[Li+]>>CC(C)(C)OC(=O)N1CC[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CO | US07388027B2_0219grants | ede03ac10e9c3ae119ddc813b7675b20217c31b9d907de83f7acf689 | C1CCOC1.CC[BH-](CC)CC.CO[C:21]([C@H:20]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][C@@H:11]1[O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22].[Li+] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]([O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[C@H:20]1[CH2:21][OH:22] | ([#7:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])>>(C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#7:4]) | 3afe965be5653824e9a8caf1aedff2bd3a5962b17fce8af753e47548 | 1 | 1 | C1CCOC1.CC[BH-](CC)CC.[Li+] | 430 |
299,773 | 976,174 | 1,644,129 | Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]([NH:13][CH2:14][C:15]3[C:16]([OH:23])=[N:17][C:18]([CH3:22])=[CH:19][C:20]=3[CH3:21])=[O:12])=[C:9]([CH3:24])[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:6]=2[N:7]=1>N1CCCC1>[OH:23][C:16]1[C:15]([CH2:14][NH:13][C:11]([C:10]2[C:5]3[CH:4]=[N:3][C:2]([N:8]4[CH2:9][CH2:10][CH2:5][CH2:6]4)=[N:7][C:6]=3[N:8]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:9]=2[CH3:24])=[O:12])=[C:20]([CH3:21])[CH:19]=[C:18]([CH3:22])[N:17]=1 | null | US09085583B2_0342 | 2,015 | Cl[c:25]1[n:24][c:23]2[n:14]([C@H:15]([CH3:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:12]([CH3:13])[c:11]([C:9]([NH:8][CH2:7][c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[n:36][c:34]3[OH:35])=[O:10])[c:33]2[cH:32][n:31]1.[NH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][NH:8][C:9](=[O:10])[c:11]2[c:12]([CH3:13])[n:14]([C@H:15]([CH3:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[n:24][c:25]([N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[n:31][cH:32][c:33]23)[c:34]([OH:35])[n:36]1 | 0.914767 | C1CCNC1.Cc1cc(C)c(CNC(=O)c2c(C)n([C@H](C)c3ccccc3)c3nc(Cl)ncc23)c(O)n1>>Cc1cc(C)c(CNC(=O)c2c(C)n([C@H](C)c3ccccc3)c3nc(N4CCCC4)ncc23)c(O)n1 | C1CCNC1.Cc1cc(C)c(CNC(=O)c2c(C)n([C@H](C)c3ccccc3)c3nc(Cl)ncc23)c(O)n1>>Cc1cc(C)c(CNC(=O)c2c(C)n([C@H](C)c3ccccc3)c3nc(N4CCCC4)ncc23)c(O)n1 | US09085583B2_0342grants | 7b45a35a544b3373fd5690d4288f6f84d31f2dd134137221d86fe40d | Cl[c:25]1[n:24][c:23]2[n:14]([C@H:15]([CH3:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:12]([CH3:13])[c:11]([C:9]([NH:8][CH2:7][c:6]3[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[n:36][c:34]3[OH:35])=[O:10])[c:33]2[cH:32][n:31]1.[NH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1 | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([CH2:7][NH:8][C:9](=[O:10])[c:11]2[c:12]([CH3:13])[n:14]([C@H:15]([CH3:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[n:24][c:25]([N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[n:31][cH:32][c:33]23)[c:34]([OH:35])[n:36]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | b57905a5bce8517a4e40b0e20794e889407f66a0ae3d7a09e7fbb00e | 1 | 1 | null | 36 |
347,446 | 430,437 | null | C[O:2][C:3]([C:5]([CH3:53])([CH3:52])[CH2:6][O:7][C:8]([N:10]1[C:19]2[C:14](=[N:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C@@H:13]([NH:22][C:23]2[N:28]=[C:27]([CH2:29][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=3)[C:26]([O:44][CH2:45][CH2:46][CH2:47][C:48]#[N:49])=[CH:25][N:24]=2)[CH2:12][C@H:11]1[CH2:50][CH3:51])=[O:9])=[O:4].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:3]([C:5]([CH3:52])([CH3:53])[CH2:6][O:7][C:8]([N:10]1[C:19]2[C:14](=[N:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C@@H:13]([NH:22][C:23]2[N:28]=[C:27]([CH2:29][C:30]3[CH:35]=[C:34]([C:36]([F:37])([F:39])[F:38])[CH:33]=[C:32]([C:40]([F:41])([F:43])[F:42])[CH:31]=3)[C:26]([O:44][CH2:45][CH2:46][CH2:47][C:48]#[N:49])=[CH:25][N:24]=2)[CH2:12][C@H:11]1[CH2:50][CH3:51])=[O:9])([OH:4])=[O:2] | |f:1.2| | US20070032485A1_1295 | 2,007 | CCO.C[O:52][C:50]([C:47]([CH2:46][O:45][C:43]([N:42]1[C@H:3]([CH2:2][CH3:1])[CH2:4][C@H:5]([NH:6][c:7]2[n:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[c:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[n:33]2)[c:34]2[n:35][c:36]([O:37][CH3:38])[cH:39][cH:40][c:41]21)=[O:44])([CH3:48])[CH3:49])=[O:51].O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].[OH-]>>[CH3:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]([NH:6][c:7]2[n:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[c:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[n:33]2)[c:34]2[n:35][c:36]([O:37][CH3:38])[cH:39][cH:40][c:41]2[N:42]1[C:43](=[O:44])[O:45][CH2:46][C:47]([CH3:48])([CH3:49])[C:50](=[O:51])[OH:52] | 0.076158 | CCO.CC[C@@H]1C[C@H](Nc2ncc(OCCCC#N)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)c2nc(OC)ccc2N1C(=O)OCC(C)(C)C(=O)OC.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+]~[OH-]>>CC[C@@H]1C[C@H](Nc2ncc(OCCCC#N)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)c2nc(OC)ccc2N1C(=O)OCC(C)(C)C(=O)O | CCO.CC[C@@H]1C[C@H](Nc2ncc(OCCCC#N)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)c2nc(OC)ccc2N1C(=O)OCC(C)(C)C(=O)OC.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].[OH-]>>CC[C@@H]1C[C@H](Nc2ncc(OCCCC#N)c(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)n2)c2nc(OC)ccc2N1C(=O)OCC(C)(C)C(=O)O | US20070032485A1_1295apps | 209230d4325fecb5dc252eb24556887f10497a6e9ed303713a3301c7 | CCO.C[O:52][C:50]([C:47]([CH2:46][O:45][C:43]([N:42]1[C@H:3]([CH2:2][CH3:1])[CH2:4][C@H:5]([NH:6][c:7]2[n:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[c:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[n:33]2)[c:34]2[n:35][c:36]([O:37][CH3:38])[cH:39][cH:40][c:41]21)=[O:44])([CH3:48])[CH3:49])=[O:51].O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].[OH-] | [CH3:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]([NH:6][c:7]2[n:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[c:17]([CH2:18][c:19]3[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[n:33]2)[c:34]2[n:35][c:36]([O:37][CH3:38])[cH:39][cH:40][c:41]2[N:42]1[C:43](=[O:44])[O:45][CH2:46][C:47]([CH3:48])([CH3:49])[C:50](=[O:51])[OH:52] | ([C:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])(-[C;D1;H3:6])-[C;D1;H3:7]) | 5f9f35ee69ba1d8ca146fb477767bb3831800b99139e61ba7a568acb | 1 | 1 | CCO.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+].[OH-] | 361 |
266,861 | 877,907 | 1,461,385 | C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]([NH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[O:26])=[C:20]2[N:19]=[CH:18][C:17]=1[C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:37][CH2:36]1)=[O:34])C1C=CC=CC=1>C1COCC1.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]([NH:27][S:28]([CH2:31][CH3:32])(=[O:29])=[O:30])=[O:26])=[C:20]2[N:19]=[CH:18][C:17]=1[C:33]([N:35]1[CH2:36][CH2:37][CH:38]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:39][CH2:40]1)=[O:34] | null | US08729264B2_0514 | 2,014 | C1CCOC1.[Pd].c1ccc(C[O:21][c:20]2[c:15]([NH:14][c:13]3[n:12]4[n:11][cH:10][c:9]([C:7]([NH:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])=[O:8])[c:39]4[n:38][cH:37][c:22]3[C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH:28]([c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[cH:16][cH:17][cH:18][cH:19]2)cc1>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][C:7](=[O:8])[c:9]1[cH:10][n:11][n:12]2[c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[OH:21])[c:22]([C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH:28]([c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[cH:37][n:38][c:39]12 | 0.577258 | C1CCOC1.CCS(=O)(=O)NC(=O)c1cnn2c(Nc3ccccc3OCc3ccccc3)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12.[Pd]>>CCS(=O)(=O)NC(=O)c1cnn2c(Nc3ccccc3O)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | C1CCOC1.CCS(=O)(=O)NC(=O)c1cnn2c(Nc3ccccc3OCc3ccccc3)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12.[Pd]>>CCS(=O)(=O)NC(=O)c1cnn2c(Nc3ccccc3O)c(C(=O)N3CCC(c4ccccc4)CC3)cnc12 | US08729264B2_0514grants | f6553bd0c397d833379d5e01ecd5482982944d96255826c7109ca1f0 | C1CCOC1.[Pd].c1ccc(C[O:21][c:20]2[c:15]([NH:14][c:13]3[n:12]4[n:11][cH:10][c:9]([C:7]([NH:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])=[O:8])[c:39]4[n:38][cH:37][c:22]3[C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH:28]([c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[cH:16][cH:17][cH:18][cH:19]2)cc1 | [CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][C:7](=[O:8])[c:9]1[cH:10][n:11][n:12]2[c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[OH:21])[c:22]([C:23](=[O:24])[N:25]3[CH2:26][CH2:27][CH:28]([c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[CH2:35][CH2:36]3)[cH:37][n:38][c:39]12 | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | C1CCOC1.[Pd] | 23 |
125,178 | 461,034 | 780,559 | [NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:4][N:3]=1>C(O)(C(F)(F)F)=O.ClCCl>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:6]=3[S:10][CH:9]=2)=[CH:16][CH:15]=1 | null | US07202363B2_0503 | 2,007 | CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]3[c:10](-[c:11]4[cH:12][cH:13][n:14][cH:15][cH:16]4)[cH:17][n:18][c:19]([NH2:20])[c:21]23)[cH:22][cH:23]1.ClCCl.O=C(O)C(F)(F)F>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]3[c:10](-[c:11]4[cH:12][cH:13][n:14][cH:15][cH:16]4)[cH:17][n:18][c:19]([NH2:20])[c:21]23)[cH:22][cH:23]1 | 0.93106 | CC(C)(C)OC(=O)Nc1ccc(-c2csc3c(-c4ccncc4)cnc(N)c23)cc1.ClCCl.O=C(O)C(F)(F)F>>Nc1ccc(-c2csc3c(-c4ccncc4)cnc(N)c23)cc1 | CC(C)(C)OC(=O)Nc1ccc(-c2csc3c(-c4ccncc4)cnc(N)c23)cc1.ClCCl.O=C(O)C(F)(F)F>>Nc1ccc(-c2csc3c(-c4ccncc4)cnc(N)c23)cc1 | US07202363B2_0503grants | 9e88ece6fa4e87032d321677ec0390f919c9984266b51dd9fe11bf89 | CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]3[c:10](-[c:11]4[cH:12][cH:13][n:14][cH:15][cH:16]4)[cH:17][n:18][c:19]([NH2:20])[c:21]23)[cH:22][cH:23]1.ClCCl.O=C(O)C(F)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]3[c:10](-[c:11]4[cH:12][cH:13][n:14][cH:15][cH:16]4)[cH:17][n:18][c:19]([NH2:20])[c:21]23)[cH:22][cH:23]1 | ([NH2;D1;+0:1]-[c:2])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]) | 5f978a847bba3863bf5fb6d96bfd1d3cace2da93615c40c010102dd5 | 0.5 | 2 | ClCCl.O=C(O)C(F)(F)F | 782 |
104,789 | 399,914 | 683,395 | [CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[O:6][C:7]2[CH:13]=[C:12]([C:14]([O:16]C)=[O:15])[CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH3:2].[OH-].[Na+]>CO.O>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[O:6][C:7]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH3:20] | |f:1.2| | US06894042B2_0658 | 2,005 | CO.C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]2[cH:9][c:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])[o:19][c:18]2[cH:17]1)=[O:15].O.[Na+].[OH-]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][c:10]2[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][c:18]2[o:19]1 | 0.771355 | CCOC(OCC)c1cc2ccc(C(=O)OC)cc2o1.CO.O.[Na+]~[OH-]>>CCOC(OCC)c1cc2ccc(C(=O)O)cc2o1 | CCOC(OCC)c1cc2ccc(C(=O)OC)cc2o1.CO.O.[Na+].[OH-]>>CCOC(OCC)c1cc2ccc(C(=O)O)cc2o1 | US06894042B2_0658grants | 197903afc0e20ecd4326ae72275839badc345cda4f77e5df498816e7 | CO.C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]2[cH:9][c:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])[o:19][c:18]2[cH:17]1)=[O:15].O.[Na+].[OH-] | [CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][c:10]2[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][c:18]2[o:19]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | CO.O.[Na+].[OH-] | 247 |
141,153 | 509,341 | 854,527 | C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[CH:11][C:10]=1[C:17](=[O:20])[CH2:18][CH3:19].[F:21][C:22]([F:35])([F:34])[S:23](O[S:23]([C:22]([F:35])([F:34])[F:21])(=[O:25])=[O:24])(=[O:25])=[O:24]>CN(C1C=CN=CC=1)C.C(Cl)Cl.[Cl-].[NH4+]>[F:21][C:22]([F:35])([F:34])[S:23]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH3:16])=[CH:11][C:10]=1[C:17](=[O:20])[CH2:18][CH3:19])(=[O:25])=[O:24] | |f:5.6| | US07419990B2_0678 | 2,008 | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.O=S(=O)(O[S:14](=[O:15])(=[O:16])[C:17]([F:18])([F:19])[F:20])C(F)(F)F.[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]1[OH:13].[Cl-].[NH4+]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]1[O:13][S:14](=[O:15])(=[O:16])[C:17]([F:18])([F:19])[F:20] | 0.125984 | CCC(=O)c1cc(C)c(C)cc1O.CCN(CC)CC.CN(C)c1ccncc1.ClCCl.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.[Cl-]~[NH4+]>>CCC(=O)c1cc(C)c(C)cc1OS(=O)(=O)C(F)(F)F | CCC(=O)c1cc(C)c(C)cc1O.CCN(CC)CC.CN(C)c1ccncc1.ClCCl.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.[Cl-].[NH4+]>>CCC(=O)c1cc(C)c(C)cc1OS(=O)(=O)C(F)(F)F | US07419990B2_0678grants | bcc07b1bcb2c48580fe1e2e05f5ff52190b7dfb922aea04836d69f5d | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.O=S(=O)(O[S:14](=[O:15])(=[O:16])[C:17]([F:18])([F:19])[F:20])C(F)(F)F.[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]1[OH:13].[Cl-].[NH4+] | [CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]([CH3:10])[cH:11][c:12]1[O:13][S:14](=[O:15])(=[O:16])[C:17]([F:18])([F:19])[F:20] | ([F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9])>>(F-C(-F)(-F)-S(=O)(=O)-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]).([OH;D1;+0:8]-[c:9]) | 99db519e153161d9e1a0b089bc1dd8038bb89ab236fbb46bac2ac4f7 | 1 | 1 | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.[Cl-].[NH4+] | 731 |
438,481 | 1,897,410 | null | [Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:13][NH:14][O:15][CH3:16].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([N:14]([O:15][CH3:16])[CH3:13])=[O:5] | |f:1.2,3.4| | US20160184265A1_0361 | 2,016 | CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.ClCCl.O[C:5](=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14].Oc1cccc2[nH]nnc12.[CH3:1][O:2][NH:3][CH3:4]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14] | 0.84262 | CCN(CC)CC.CCN=C=NCCCN(C)C~Cl.CNOC~Cl.ClCCl.O=C(O)c1cc(F)ccc1Br.Oc1cccc2[nH]nnc12>>CON(C)C(=O)c1cc(F)ccc1Br | CCN(CC)CC.CCN=C=NCCCN(C)C.CNOC.Cl.Cl.ClCCl.O=C(O)c1cc(F)ccc1Br.Oc1cccc2[nH]nnc12>>CON(C)C(=O)c1cc(F)ccc1Br | US20160184265A1_0361apps | 19ea25979296f0c028fe45c0b2cd2a570bd28dccba4cc1ee66a10013 | CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.ClCCl.O[C:5](=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14].Oc1cccc2[nH]nnc12.[CH3:1][O:2][NH:3][CH3:4] | [CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14] | ([#8:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([#8:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | 2c3224680b195d696d0882709f61e7f76f8fe83ee63f8bfe6da01746 | 1 | 1 | CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.Cl.ClCCl.Oc1cccc2[nH]nnc12 | 828 |
176,738 | 615,608 | 1,020,785 | [Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20] | |f:2.3,5.6| | US07812017B2_0932 | 2,010 | CCCC[N+](CCCC)(CCCC)CCCC.ClCCl.Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=S(=O)([O-])O.[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][nH:10][c:20]2[cH:21]1.[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][n:10]([S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]2[cH:21]1 | 0.593055 | CCCC[N+](CCCC)(CCCC)CCCC~O=S(=O)([O-])O.COc1cc(Br)c2cc[nH]c2c1.ClCCl.O=S(=O)(Cl)c1ccccc1.[Na+]~[OH-]>>COc1cc(Br)c2ccn(S(=O)(=O)c3ccccc3)c2c1 | CCCC[N+](CCCC)(CCCC)CCCC.COc1cc(Br)c2cc[nH]c2c1.ClCCl.O=S(=O)(Cl)c1ccccc1.O=S(=O)([O-])O.[Na+].[OH-]>>COc1cc(Br)c2ccn(S(=O)(=O)c3ccccc3)c2c1 | US07812017B2_0932grants | d0acd2ec827464c435c6902a6b0d94a44ce8eace1ed7b619faba9d92 | CCCC[N+](CCCC)(CCCC)CCCC.ClCCl.Cl[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=S(=O)([O-])O.[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][nH:10][c:20]2[cH:21]1.[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[cH:8][cH:9][n:10]([S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]2[cH:21]1 | ([O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4])-[n;H0;D3;+0:6](:[c:5]):[c:7])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([c:5]:[nH;D2;+0:6]:[c:7]) | 76e5dcfc59d0995646419a7b5366f6a558a5c3ba2bb1ac4fcad7138b | 1 | 1 | CCCC[N+](CCCC)(CCCC)CCCC.ClCCl.O=S(=O)([O-])O.[Na+].[OH-] | 648 |