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
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
421,416 | 1,772,462 | null | F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([F:16])([F:15])[F:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C([O-])([O-])=O.[K+].[K+].[CH2:26]([SH:28])[CH3:27].O>CN(C)C=O>[CH2:26]([S:28][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([F:16])([F:15])[F:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])[CH3:27] | |f:1.2.3| | US20150299115A1_0817 | 2,015 | CN(C)C=O.F[c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][CH2:12][C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21].O.O=C([O-])[O-].[CH3:1][CH2:2][SH:3].[K+].[K+]>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][CH2:12][C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | 0.161185 | CCS.CN(C)C=O.O.O=C([O-])[O-]~[K+]~[K+].O=[N+]([O-])c1cc(S(=O)(=O)NCC(F)(F)F)ccc1F>>CCSc1ccc(S(=O)(=O)NCC(F)(F)F)cc1[N+](=O)[O-] | CCS.CN(C)C=O.O.O=C([O-])[O-].O=[N+]([O-])c1cc(S(=O)(=O)NCC(F)(F)F)ccc1F.[K+].[K+]>>CCSc1ccc(S(=O)(=O)NCC(F)(F)F)cc1[N+](=O)[O-] | US20150299115A1_0817apps | 78828467f6421e1874bd517d6f8366789ef2dd358bb803d7cf5988fa | CN(C)C=O.F[c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][CH2:12][C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21].O.O=C([O-])[O-].[CH3:1][CH2:2][SH:3].[K+].[K+] | [CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][CH2:12][C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | ([C:4]-[S;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]-[SH;D1;+0:5]) | d34413d549bac0a76470269d53b823119a6b48ff5574636df4cb6c3e | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 503 |
243,024 | 809,178 | 1,340,629 | [C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[O:9])[CH:2]=1.Cl.[NH2:12][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=[O:32])[N:17]([CH:24]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31])[C:18]2=[O:23].C(N(CC)CC)C>C1COCC1>[O:31]=[C:25]1[CH:24]([N:17]2[C:16](=[O:32])[C:15]3[C:19](=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13][NH:12][C:8]([NH:7][C:3]3[CH:2]=[C:1]([CH3:10])[CH:6]=[CH:5][CH:4]=3)=[O:9])[C:18]2=[O:23])[CH2:29][CH2:28][C:27](=[O:30])[NH:26]1 | |f:1.2| | US08481568B2_0700 | 2,013 | C1CCOC1.CCN(CC)CC.Cl.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:31]1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[N:20]([CH:21]1[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]1=[O:28])[C:29]2=[O:30]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[c:17]2[C:18](=[O:19])[N:20]([CH:21]2[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]2=[O:28])[C:29]3=[O:30])[cH:31]1 | 0.966316 | C1CCOC1.CCN(CC)CC.Cc1cccc(N=C=O)c1.Cl~NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>Cc1cccc(NC(=O)NCc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)c1 | C1CCOC1.CCN(CC)CC.Cc1cccc(N=C=O)c1.Cl.NCc1cccc2c1C(=O)N(C1CCC(=O)NC1=O)C2=O>>Cc1cccc(NC(=O)NCc2cccc3c2C(=O)N(C2CCC(=O)NC2=O)C3=O)c1 | US08481568B2_0700grants | 023582f45a732ded74672fa4a830a91964be101593c4c643570c2d79 | C1CCOC1.CCN(CC)CC.Cl.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:31]1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[C:18](=[O:19])[N:20]([CH:21]1[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]1=[O:28])[C:29]2=[O:30] | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]3[c:17]2[C:18](=[O:19])[N:20]([CH:21]2[CH2:22][CH2:23][C:24](=[O:25])[NH:26][C:27]2=[O:28])[C:29]3=[O:30])[cH:31]1 | ([O;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[C:2]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1)-[NH;D2;+0:11]-[c:12])>>([NH2;D1;+0:1]-[C:2]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1).([O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12]) | 000b0cbb1f7684f838b27c9f86d2926bde2e1dd0735f7bb9a3388361 | 1 | 1 | C1CCOC1.CCN(CC)CC.Cl | 814 |
211,708 | 714,165 | 1,175,731 | [F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([C:13]1[C:21]2[CH:20]=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1)=[O:12].O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.O1CCCC1>[NH2:8][C:7]1[C:2]([F:1])=[C:3]([C:11]([C:13]2[C:21]3[CH:20]=[N:19][CH:18]=[N:17][C:16]=3[NH:15][CH:14]=2)=[O:12])[CH:4]=[CH:5][CH:6]=1 | |f:2.3| | US08153641B2_0526 | 2,012 | C1CCOC1.CCO.CCOC(C)=O.O.O=C([O-])O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][nH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]23)[c:18]1[F:19].[Na+]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][nH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]23)[c:18]1[F:19] | 0.975489 | C1CCOC1.CCO.CCOC(C)=O.O.O=C([O-])O~[Na+].O=C(c1cccc([N+](=O)[O-])c1F)c1c[nH]c2ncncc12>>Nc1cccc(C(=O)c2c[nH]c3ncncc23)c1F | C1CCOC1.CCO.CCOC(C)=O.O.O=C([O-])O.O=C(c1cccc([N+](=O)[O-])c1F)c1c[nH]c2ncncc12.[Na+]>>Nc1cccc(C(=O)c2c[nH]c3ncncc23)c1F | US08153641B2_0526grants | 898a095791de5f504b21a36e62a71884ab568f405d563ac627bddf98 | C1CCOC1.CCO.CCOC(C)=O.O.O=C([O-])O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][nH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]23)[c:18]1[F:19].[Na+] | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][nH:11][c:12]3[n:13][cH:14][n:15][cH:16][c:17]23)[c:18]1[F:19] | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | C1CCOC1.CCO.CCOC(C)=O.O.O=C([O-])O.[Na+] | 1 |
160,918 | 569,100 | 948,894 | Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:11]=[C:10]([CH3:26])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[C:27]([NH:31][S:32]([C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:34])=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([NH:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[C:39]([C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([O:24][CH3:25])[CH:15]=4)[CH:11]=[C:10]([CH3:26])[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:40]=1)(=[O:34])=[O:33])([CH3:30])([CH3:28])[CH3:29] | null | US07642264B2_1674 | 2,010 | Cl[c:16]1[n:15][cH:14][cH:13][c:12](-[c:11]2[n:10][c:8]([CH3:9])[cH:7][c:6](-[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:35]([C:36]([F:37])([F:38])[F:39])[cH:34][cH:33]3)[cH:32]2)[cH:31]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([S:22](=[O:23])(=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([CH3:9])[n:10][c:11](-[c:12]3[cH:13][cH:14][n:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]([S:22](=[O:23])(=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]4)[cH:31]3)[cH:32]2)[cH:33][cH:34][c:35]1[C:36]([F:37])([F:38])[F:39] | 0.094713 | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.COc1cc(-c2cc(C)nc(-c3ccnc(Cl)c3)c2)ccc1C(F)(F)F>>COc1cc(-c2cc(C)nc(-c3ccnc(-c4cccc(S(=O)(=O)NC(C)(C)C)c4)c3)c2)ccc1C(F)(F)F | CC(C)(C)NS(=O)(=O)c1cccc(B(O)O)c1.COc1cc(-c2cc(C)nc(-c3ccnc(Cl)c3)c2)ccc1C(F)(F)F>>COc1cc(-c2cc(C)nc(-c3ccnc(-c4cccc(S(=O)(=O)NC(C)(C)C)c4)c3)c2)ccc1C(F)(F)F | US07642264B2_1674grants | dbed34186247b63f48f573928d6df284cd683ea7baf29f51efe612cb | Cl[c:16]1[n:15][cH:14][cH:13][c:12](-[c:11]2[n:10][c:8]([CH3:9])[cH:7][c:6](-[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:35]([C:36]([F:37])([F:38])[F:39])[cH:34][cH:33]3)[cH:32]2)[cH:31]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][c:21]([S:22](=[O:23])(=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]1 | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([CH3:9])[n:10][c:11](-[c:12]3[cH:13][cH:14][n:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]([S:22](=[O:23])(=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]4)[cH:31]3)[cH:32]2)[cH:33][cH:34][c:35]1[C:36]([F:37])([F:38])[F:39] | ([#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 | 0.5 | 2 | null | 865 |
303,967 | 988,021 | 1,666,576 | [CH3:1][C:2]1([CH3:22])[C:15]2[C:10]3=[C:11]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[CH:13][CH:14]=2.C1C(=O)N([Br:30])C(=O)C1.O>C(Cl)Cl.C(#N)C>[Br:30][C:18]1[CH:19]=[CH:20][C:21]2[N:9]3[C:8]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[C:2]([CH3:22])([CH3:1])[C:15]4[C:10]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:16]=2[CH:17]=1 | null | US09133119B2_0183 | 2,015 | CC#N.ClCCl.O.O=C1CCC(=O)N1[Br:15].[CH3:1][C:2]1([CH3:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[n:10]2[c:11]3[cH:12][cH:13][cH:14][cH:16][c:17]3[c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]23>>[CH3:1][C:2]1([CH3:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[n:10]2[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]23 | 0.88924 | CC#N.CC1(C)c2ccccc2-n2c3ccccc3c3cccc1c32.ClCCl.O.O=C1CCC(=O)N1Br>>CC1(C)c2ccccc2-n2c3ccc(Br)cc3c3cccc1c32 | CC#N.CC1(C)c2ccccc2-n2c3ccccc3c3cccc1c32.ClCCl.O.O=C1CCC(=O)N1Br>>CC1(C)c2ccccc2-n2c3ccc(Br)cc3c3cccc1c32 | US09133119B2_0183grants | 7725b2f81d460410b77523fd411e43a60ceeb9d25fe324e97e42fcc1 | CC#N.ClCCl.O.O=C1CCC(=O)N1[Br:15].[CH3:1][C:2]1([CH3:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[n:10]2[c:11]3[cH:12][cH:13][cH:14][cH:16][c:17]3[c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]23 | [CH3:1][C:2]1([CH3:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2-[n:10]2[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[c:18]3[cH:19][cH:20][cH:21][c:22]1[c:23]23 | ([Br;H0;D1;+0:1]-[c;H0;D3;+0:3](:[c:2]):[c:4])>>(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1]).([c:2]:[cH;D2;+0:3]:[c:4]) | 04aac57316494f5621172b80523cd496e017f4d0104703ad33b2fa4b | 1 | 1 | CC#N.ClCCl.O | 4 |
123,907 | 457,073 | 774,291 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:39]1[C:44]([OH:45])=[CH:43][C:42]2[C:46]([CH2:49][CH2:50][NH2:51])=[CH:47][NH:48][C:41]=2[CH:40]=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[OH:45][C:44]1[CH:43]=[C:42]2[C:41](=[CH:40][CH:39]=1)[NH:48][CH:47]=[C:46]2[CH2:49][CH2:50][NH:51][C:20](=[O:22])[CH2:19][CH2:18][CH2:17]/[CH:16]=[CH:15]\[CH2:14][C@H:13]1[C@@H:12]([OH:23])[CH2:11][C@@H:10]([OH:24])[C@@H:9]1/[CH:8]=[CH:7]/[C@@H:6]([OH:25])[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1] | |f:3.4| | US07186744B2_0095 | 2,007 | CCN(CC)CC.CCOC(=O)Cl.CCOC(C)=O.Cl.ClCCl.O[C:23]([CH2:22][CH2:21][CH2:20]/[CH:19]=[CH:18]\[CH2:17][C@@H:16]1[C@@H:10](/[CH:9]=[CH:8]/[C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:7])[C@H:11]([OH:12])[CH2:13][C@@H:14]1[OH:15])=[O:24].[NH2:25][CH2:26][CH2:27][c:28]1[cH:29][nH:30][c:31]2[cH:32][cH:33][c:34]([OH:35])[cH:36][c:37]12>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])/[CH:8]=[CH:9]/[C@H:10]1[C@H:11]([OH:12])[CH2:13][C@H:14]([OH:15])[C@@H:16]1[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[NH:25][CH2:26][CH2:27][c:28]1[cH:29][nH:30][c:31]2[cH:32][cH:33][c:34]([OH:35])[cH:36][c:37]12 | 0.921681 | CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O.CCN(CC)CC.CCOC(=O)Cl.CCOC(C)=O.ClCCl.Cl~NCCc1c[nH]c2ccc(O)cc12>>CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)NCCc1c[nH]c2ccc(O)cc12 | CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O.CCN(CC)CC.CCOC(=O)Cl.CCOC(C)=O.Cl.ClCCl.NCCc1c[nH]c2ccc(O)cc12>>CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)NCCc1c[nH]c2ccc(O)cc12 | US07186744B2_0095grants | fa76ce922ac7dbdbde57ffef03600b18b347daa1d7470bdb39f37d53 | CCN(CC)CC.CCOC(=O)Cl.CCOC(C)=O.Cl.ClCCl.O[C:23]([CH2:22][CH2:21][CH2:20]/[CH:19]=[CH:18]\[CH2:17][C@@H:16]1[C@@H:10](/[CH:9]=[CH:8]/[C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:7])[C@H:11]([OH:12])[CH2:13][C@@H:14]1[OH:15])=[O:24].[NH2:25][CH2:26][CH2:27][c:28]1[cH:29][nH:30][c:31]2[cH:32][cH:33][c:34]([OH:35])[cH:36][c:37]12 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])/[CH:8]=[CH:9]/[C@H:10]1[C@H:11]([OH:12])[CH2:13][C@H:14]([OH:15])[C@@H:16]1[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[NH:25][CH2:26][CH2:27][c:28]1[cH:29][nH:30][c:31]2[cH:32][cH:33][c:34]([OH:35])[cH:36][c:37]12 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 1 | 1 | CCN(CC)CC.CCOC(=O)Cl.CCOC(C)=O.Cl.ClCCl | 230 |
329,119 | 40,078 | null | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:39])[CH2:16][NH:17][C@H:18]([CH2:37][OH:38])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:40][S:41]([CH3:44])(=[O:43])=[O:42])C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:39])[CH2:16][NH:17][C@H:18]([CH2:37][OH:38])[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:24][CH:25]=2)=[CH:11][C:10]=1[NH:40][S:41]([CH3:44])(=[O:43])=[O:42] | null | US20020143034A1_0479 | 2,002 | CO.[H][H].[Pd].c1ccc(C[O:37][c:36]2[c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][C@H:13]([CH2:14][OH:15])[CH2:16][c:17]3[cH:18][cH:19][c:20]([O:21][c:22]4[cH:23][cH:24][c:25]5[cH:26][cH:27][cH:28][cH:29][c:30]5[n:31]4)[cH:32][cH:33]3)[cH:34][cH:35]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][C@H:13]([CH2:14][OH:15])[CH2:16][c:17]2[cH:18][cH:19][c:20]([O:21][c:22]3[cH:23][cH:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[n:31]3)[cH:32][cH:33]2)[cH:34][cH:35][c:36]1[OH:37] | 0.591956 | CO.CS(=O)(=O)Nc1cc([C@@H](O)CN[C@H](CO)Cc2ccc(Oc3ccc4ccccc4n3)cc2)ccc1OCc1ccccc1.[H][H].[Pd]>>CS(=O)(=O)Nc1cc([C@@H](O)CN[C@H](CO)Cc2ccc(Oc3ccc4ccccc4n3)cc2)ccc1O | CO.CS(=O)(=O)Nc1cc([C@@H](O)CN[C@H](CO)Cc2ccc(Oc3ccc4ccccc4n3)cc2)ccc1OCc1ccccc1.[H][H].[Pd]>>CS(=O)(=O)Nc1cc([C@@H](O)CN[C@H](CO)Cc2ccc(Oc3ccc4ccccc4n3)cc2)ccc1O | US20020143034A1_0479apps | 242e93536aac2c7a35d4e1af6e0601ff4c6e7ca8db13eba0153f972d | CO.[H][H].[Pd].c1ccc(C[O:37][c:36]2[c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][C@H:13]([CH2:14][OH:15])[CH2:16][c:17]3[cH:18][cH:19][c:20]([O:21][c:22]4[cH:23][cH:24][c:25]5[cH:26][cH:27][cH:28][cH:29][c:30]5[n:31]4)[cH:32][cH:33]3)[cH:34][cH:35]2)cc1 | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([C@@H:9]([OH:10])[CH2:11][NH:12][C@H:13]([CH2:14][OH:15])[CH2:16][c:17]2[cH:18][cH:19][c:20]([O:21][c:22]3[cH:23][cH:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[n:31]3)[cH:32][cH:33]2)[cH:34][cH:35][c:36]1[OH:37] | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | CO.[H][H].[Pd] | 23 |
332,838 | 155,360 | null | O.NN.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]3[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]=13)[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N:11][C:10]([CH2:28][N:29]1C(=O)C3C(=CC=CC=3)C1=O)([CH3:27])[CH2:9]2.[OH-].[Na+]>C(O)C.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]3[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][C:15]=13)[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N:11][C:10]([CH3:27])([CH2:28][NH2:29])[CH2:9]2 | |f:0.1,3.4| | US20040092582A1_3659 | 2,004 | CCO.NN.O.O.O=C1c2ccccc2C(=O)[N:25]1[CH2:24][C:22]1([CH3:23])[N:21]=[C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]3[c:7]2[CH2:13][C:10]([CH3:11])([CH3:12])[O:9]3)[CH2:26]1.[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]3[c:8]1[O:9][C:10]([CH3:11])([CH3:12])[CH2:13]3)[C:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[N:21][C:22]([CH3:23])([CH2:24][NH2:25])[CH2:26]2 | 0.583313 | CCO.COc1cc2c(c3c1OC(C)(C)C3)C(c1ccccc1)=NC(C)(CN1C(=O)c3ccccc3C1=O)C2.NN~O.O.[Na+]~[OH-]>>COc1cc2c(c3c1OC(C)(C)C3)C(c1ccccc1)=NC(C)(CN)C2 | CCO.COc1cc2c(c3c1OC(C)(C)C3)C(c1ccccc1)=NC(C)(CN1C(=O)c3ccccc3C1=O)C2.NN.O.O.[Na+].[OH-]>>COc1cc2c(c3c1OC(C)(C)C3)C(c1ccccc1)=NC(C)(CN)C2 | US20040092582A1_3659apps | 9d5925f1bfb8b3647a61bec40d8adfcd21f8e102ea2c179d857dcdb9 | CCO.NN.O.O.O=C1c2ccccc2C(=O)[N:25]1[CH2:24][C:22]1([CH3:23])[N:21]=[C:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]3[c:7]2[CH2:13][C:10]([CH3:11])([CH3:12])[O:9]3)[CH2:26]1.[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]3[c:8]1[O:9][C:10]([CH3:11])([CH3:12])[CH2:13]3)[C:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[N:21][C:22]([CH3:23])([CH2:24][NH2:25])[CH2:26]2 | ([C:2]-[NH2;D1;+0:1])>>(O=C1-[N;H0;D3;+0:1](-[C:2])-C(=O)-c2:c:c:c:c:c:2-1) | 7399a60fd7378a24dfa10a10ff432b29a0c80f1c6d7ac70d27cfe818 | 1 | 1 | CCO.NN.O.O.[Na+].[OH-] | 242 |
362,482 | 650,146 | null | [Cl:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=4)[N:20]=[C:19](Cl)[N:18]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.Cl.Cl.[N:36]1[CH:41]=[CH:40][CH:39]=[N:38][C:37]=1[N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:28])([F:30])[F:29])[CH:25]=4)[N:20]=[C:19]([N:45]4[CH2:46][CH2:47][N:42]([C:37]5[N:36]=[CH:41][CH:40]=[CH:39][N:38]=5)[CH2:43][CH2:44]4)[N:18]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1 | |f:1.2.3| | US20090004185A1_0550 | 2,009 | Cl.Cl.Cl[c:12]1[n:11][c:10]([NH:9][CH2:8][c:7]2[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:38]3[cH:39][cH:40][c:41]([Cl:42])[cH:43][cH:44]3)[cH:37][cH:36]2)[c:35]2[c:26]([n:25]1)[cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]2.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[n:18][cH:19][cH:20][cH:21][n:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[n:11][c:12]([N:13]3[CH2:14][CH2:15][N:16]([c:17]4[n:18][cH:19][cH:20][cH:21][n:22]4)[CH2:23][CH2:24]3)[n:25][c:26]3[cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][c:35]23)[cH:36][cH:37]1)[c:38]1[cH:39][cH:40][c:41]([Cl:42])[cH:43][cH:44]1 | 0.188672 | Cl~Cl~c1cnc(N2CCNCC2)nc1.O=C(Nc1ccc(CNc2nc(Cl)nc3ccc(C(F)(F)F)cc23)cc1)c1ccc(Cl)cc1>>O=C(Nc1ccc(CNc2nc(N3CCN(c4ncccn4)CC3)nc3ccc(C(F)(F)F)cc23)cc1)c1ccc(Cl)cc1 | Cl.Cl.O=C(Nc1ccc(CNc2nc(Cl)nc3ccc(C(F)(F)F)cc23)cc1)c1ccc(Cl)cc1.c1cnc(N2CCNCC2)nc1>>O=C(Nc1ccc(CNc2nc(N3CCN(c4ncccn4)CC3)nc3ccc(C(F)(F)F)cc23)cc1)c1ccc(Cl)cc1 | US20090004185A1_0550apps | e13ad518b830ba25beafee8c493c61028947d0829f23c9fcdd810ba0 | Cl.Cl.Cl[c:12]1[n:11][c:10]([NH:9][CH2:8][c:7]2[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[c:38]3[cH:39][cH:40][c:41]([Cl:42])[cH:43][cH:44]3)[cH:37][cH:36]2)[c:35]2[c:26]([n:25]1)[cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]2.[NH:13]1[CH2:14][CH2:15][N:16]([c:17]2[n:18][cH:19][cH:20][cH:21][n:22]2)[CH2:23][CH2:24]1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[n:11][c:12]([N:13]3[CH2:14][CH2:15][N:16]([c:17]4[n:18][cH:19][cH:20][cH:21][n:22]4)[CH2:23][CH2:24]3)[n:25][c:26]3[cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][c:35]23)[cH:36][cH:37]1)[c:38]1[cH:39][cH:40][c:41]([Cl:42])[cH:43][cH:44]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 | 0.5 | 2 | Cl.Cl | 36 |
321,931 | 1,046,745 | 1,775,928 | [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]([C:13]1[CH:26]=[C:25]2[C:27]3=[C:28]4[C:18]([CH:19]=[CH:20][CH:21]=[C:22]4[CH:23]=[CH:24]2)=[CH:17][CH:16]=[C:15]3[C:14]=1[O:29]C)=[O:12].C(S)CCCCCCCCCCC.[OH-].[K+].Cl>CN(C)C=O>[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]([C:13]1[CH:26]=[C:25]2[C:27]3=[C:28]4[C:18]([CH:19]=[CH:20][CH:21]=[C:22]4[CH:23]=[CH:24]2)=[CH:17][CH:16]=[C:15]3[C:14]=1[OH:29])=[O:12] | |f:2.3| | US09371444B2_0102 | 2,016 | CCCCCCCCCCCCS.CN(C)C=O.C[O:27][c:26]1[c:13]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12]2)[cH:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][c:22]4[cH:23][cH:24][c:25]1[c:28]2[c:29]34.Cl.[K+].[OH-]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1)[c:13]1[cH:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][c:22]4[cH:23][cH:24][c:25]([c:26]1[OH:27])[c:28]2[c:29]34 | 0.907881 | CCCCCCCCCCCCS.CN(C)C=O.COc1c(C(=O)c2ccc3ccccc3c2)cc2ccc3cccc4ccc1c2c34.Cl.[K+]~[OH-]>>O=C(c1ccc2ccccc2c1)c1cc2ccc3cccc4ccc(c1O)c2c34 | CCCCCCCCCCCCS.CN(C)C=O.COc1c(C(=O)c2ccc3ccccc3c2)cc2ccc3cccc4ccc1c2c34.Cl.[K+].[OH-]>>O=C(c1ccc2ccccc2c1)c1cc2ccc3cccc4ccc(c1O)c2c34 | US09371444B2_0102grants | 35ccd2c6be56d174223126edd923b7245949eb36f3b7319e80df42f9 | CCCCCCCCCCCCS.CN(C)C=O.C[O:27][c:26]1[c:13]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12]2)[cH:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][c:22]4[cH:23][cH:24][c:25]1[c:28]2[c:29]34.Cl.[K+].[OH-] | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1)[c:13]1[cH:14][c:15]2[cH:16][cH:17][c:18]3[cH:19][cH:20][cH:21][c:22]4[cH:23][cH:24][c:25]([c:26]1[OH:27])[c:28]2[c:29]34 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | CCCCCCCCCCCCS.CN(C)C=O.Cl.[K+].[OH-] | 48 |
395,222 | 1,259,203 | null | [C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([N:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:14][CH:13]([C:27]([OH:29])=O)[CH2:12]2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[CH2:30]([O:32][CH2:33][CH2:34][C:35](=[N:37]O)[NH2:36])[CH3:31]>>[CH2:30]([O:32][CH2:33][CH2:34][C:35]1[N:37]=[C:27]([CH:13]2[CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[CH2:16][N:11]([C:9]([N:6]3[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]3)=[O:10])[CH2:12]2)[O:29][N:36]=1)[CH3:31] | null | US20120214788A1_1817 | 2,012 | O=[C:9](O)[CH:10]1[CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]2)[CH2:23][N:24]([C:25](=[O:26])[N:27]2[CH2:28][CH2:29][CH:30]([C:31]#[N:32])[CH2:33][CH2:34]2)[CH2:35]1.[CH3:1][CH2:2][O:3][CH2:4][CH2:5][C:6](=[N:7][OH:8])[NH2:36]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][c:6]1[n:7][o:8][c:9]([CH:10]2[CH2:11][CH:12]([c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[CH2:23][N:24]([C:25](=[O:26])[N:27]3[CH2:28][CH2:29][CH:30]([C:31]#[N:32])[CH2:33][CH2:34]3)[CH2:35]2)[n:36]1 | 0.242566 | CCOCCC(N)=NO.N#CC1CCN(C(=O)N2CC(C(=O)O)CC(c3ccc(C(F)(F)F)cc3)C2)CC1>>CCOCCc1noc(C2CC(c3ccc(C(F)(F)F)cc3)CN(C(=O)N3CCC(C#N)CC3)C2)n1 | CCOCCC(N)=NO.N#CC1CCN(C(=O)N2CC(C(=O)O)CC(c3ccc(C(F)(F)F)cc3)C2)CC1>>CCOCCc1noc(C2CC(c3ccc(C(F)(F)F)cc3)CN(C(=O)N3CCC(C#N)CC3)C2)n1 | US20120214788A1_1817apps | 67ec3d9bced400ce62ae144bdf377b996258e1a3fd398ff5f3b25ad5 | O=[C:9](O)[CH:10]1[CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]2)[CH2:23][N:24]([C:25](=[O:26])[N:27]2[CH2:28][CH2:29][CH:30]([C:31]#[N:32])[CH2:33][CH2:34]2)[CH2:35]1.[CH3:1][CH2:2][O:3][CH2:4][CH2:5][C:6](=[N:7][OH:8])[NH2:36] | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][c:6]1[n:7][o:8][c:9]([CH:10]2[CH2:11][CH:12]([c:13]3[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]3)[CH2:23][N:24]([C:25](=[O:26])[N:27]3[CH2:28][CH2:29][CH:30]([C:31]#[N:32])[CH2:33][CH2:34]3)[CH2:35]2)[n:36]1 | ([C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:4](-[C:3]):[n;H0;D2;+0:6]:[o;H0;D2;+0:7]:1)>>(O-[C;H0;D3;+0:1](=O)-[C:2]).([C:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5])=[N;H0;D2;+0:6]-[OH;D1;+0:7]) | 8d8cd0adafd12d737c88a33fdf09a0ca02b3501b9e40e0fcf1782773 | 1 | 1 | null | 728 |
418,357 | 1,742,404 | null | [OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][C:6]=1[O:16][CH3:17].[OH-].[K+]>CO>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:16][CH3:17] | |f:1.2| | US20150238498A1_0596 | 2,015 | CC[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH2:13][CH2:14][OH:15])[cH:10][cH:9]1)=[O:7].CO.[K+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][OH:15] | 0.960285 | CCOC(=O)c1ccc(OCCO)c(OC)c1.CO.[K+]~[OH-]>>COc1cc(C(=O)O)ccc1OCCO | CCOC(=O)c1ccc(OCCO)c(OC)c1.CO.[K+].[OH-]>>COc1cc(C(=O)O)ccc1OCCO | US20150238498A1_0596apps | 08b2316ecb39507e77202b6c478b0e2bb78359a08c418efa27640675 | CC[O:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH2:13][CH2:14][OH:15])[cH:10][cH:9]1)=[O:7].CO.[K+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][OH:15] | ([C:9]-[#8:8]-[c:7]1:[c:10]:[c:11]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:5]:[c:6]:1)>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[#8:8]-[C:9]):[c:10]:[c:11]:1) | b30d532708aa26d55eb90fc3c0c719f2184f270e69eaad1227f7f5e5 | 1 | 1 | CO.[K+].[OH-] | 386 |
33,412 | 152,331 | 244,598 | [H-].[Na+].[CH2:3]([OH:8])[CH2:4][S:5][CH2:6][CH3:7].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br>CCCCCC.C1COCC1>[CH2:10]([Br:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:8][CH2:3][CH2:4][S:5][CH2:6][CH3:7] | |f:0.1| | US05082967_ | 1,992 | Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13].C1CCOC1.CCCCCC.[CH3:1][CH2:2][S:3][CH2:4][CH2:5][OH:6].[H-].[Na+]>>[CH3:1][CH2:2][S:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13] | 0.774562 | BrCCCCCCBr.C1CCOC1.CCCCCC.CCSCCO.[H-]~[Na+]>>CCSCCOCCCCCCBr | BrCCCCCCBr.C1CCOC1.CCCCCC.CCSCCO.[H-].[Na+]>>CCSCCOCCCCCCBr | US05082967_grants | 1081cc340a1a2760db2f310d2d76aa9900c5b026cceb2a7481ced1a8 | Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13].C1CCOC1.CCCCCC.[CH3:1][CH2:2][S:3][CH2:4][CH2:5][OH:6].[H-].[Na+] | [CH3:1][CH2:2][S:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13] | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[OH;D1;+0:4]) | a4c3d230363503c3cdd0e8b3bb15c888472ef0fddbf2cfc06e03712b | 0.5 | 2 | C1CCOC1.CCCCCC.[H-].[Na+] | 95 |
33,429 | 152,387 | 244,657 | [C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30].[OH-].[Na+].C(O)(=O)C>C(O)C.O>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2] | |f:2.3| | US05084214_ | 1,992 | Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22].CC(=O)O.CCO.O.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:23][c:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]1[OH:30].[Na+].[OH-]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22])[cH:23][c:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]1[OH:30] | 0.264198 | CC(=O)O.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.CCO.O.O=C(O)CCCCCCCCCCCBr.[Na+]~[OH-]>>CC(C)(C)c1cc(SCCCCCCCCCCCC(=O)O)cc(C(C)(C)C)c1O | CC(=O)O.CC(C)(C)c1cc(S)cc(C(C)(C)C)c1O.CCO.O.O=C(O)CCCCCCCCCCCBr.[Na+].[OH-]>>CC(C)(C)c1cc(SCCCCCCCCCCCC(=O)O)cc(C(C)(C)C)c1O | US05084214_grants | 78a9856ed0c9d3b1b5af5e0bb18a26ac1e2305af38a91aa5ecb674af | Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22].CC(=O)O.CCO.O.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([SH:8])[cH:23][c:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]1[OH:30].[Na+].[OH-] | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[OH:22])[cH:23][c:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]1[OH:30] | ([C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([SH;D1;+0:3]-[c:4]) | b73d38e46252a190f18366e71c7fd160a59a139df9fb6551d999a041 | 1 | 1 | CC(=O)O.CCO.O.[Na+].[OH-] | 124 |
282,978 | 926,396 | 1,551,076 | [NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([OH:12])[CH2:4][CH2:3]1.[H-].[Na+].[C:15]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][N:18]=1)#[N:16]>CN(C=O)C>[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([O:12][C:20]2[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[N:18][CH:19]=2)[CH2:4][CH2:3]1 | |f:1.2| | US08907094B2_0740 | 2,014 | CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[n:20][cH:19]1.[H-].[Na+].[OH:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([NH2:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][C@@H:8]2[CH2:9][CH2:10][C@H:11]([NH2:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][n:20]1 | 0.902713 | CN(C)C=O.N#Cc1ccc(F)cn1.N[C@H]1CC[C@@H](O)c2ccccc21.[H-]~[Na+]>>N#Cc1ccc(O[C@@H]2CC[C@H](N)c3ccccc32)cn1 | CN(C)C=O.N#Cc1ccc(F)cn1.N[C@H]1CC[C@@H](O)c2ccccc21.[H-].[Na+]>>N#Cc1ccc(O[C@@H]2CC[C@H](N)c3ccccc32)cn1 | US08907094B2_0740grants | 6acbcae59d9851026ee32f26237401b747271dabff36e4e6acc137ef | CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[n:20][cH:19]1.[H-].[Na+].[OH:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([NH2:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][C@@H:8]2[CH2:9][CH2:10][C@H:11]([NH2:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][n:20]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[O;H0;D2;+0:6]-[C:5])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).([C:5]-[OH;D1;+0:6]) | 15666bdf05be73a7c71858cafe9dfcadc702a630a1750bc1d2f2a992 | 1 | 1 | CN(C)C=O.[H-].[Na+] | 823 |
204,331 | 694,836 | 1,145,006 | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:39])[O:14][CH2:15][C@@H:16]([N:25]([CH3:38])[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=1[Cl:37])=[O:27])[CH2:17][C:18]([F:24])([F:23])[CH2:19][N:20]=[N+]=[N-])=[CH:5]2.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:39])[O:14][CH2:15][C@@H:16]([N:25]([CH3:38])[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=1[Cl:37])=[O:27])[CH2:17][C:18]([F:23])([F:24])[CH2:19][NH2:20])=[CH:5]2 | null | US08088793B2_0842 | 2,012 | C1CCOC1.Cl.O.[N-]=[N+]=[N:37][CH2:36][C:33]([CH2:32][C@H:15]([N:2]([CH3:1])[C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[Cl:14])[CH2:16][O:17][C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]2[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]2[cH:30][n:31]1)([F:34])[F:35].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[CH3:1][N:2]([C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[Cl:14])[C@H:15]([CH2:16][O:17][C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]2[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]2[cH:30][n:31]1)[CH2:32][C:33]([F:34])([F:35])[CH2:36][NH2:37] | 0.658911 | C1CCOC1.CN(C(=O)NCc1cccc(F)c1Cl)[C@H](COC(=O)Nc1cc2cc(F)ccc2cn1)CC(F)(F)CN=[N+]=[N-].Cl.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CN(C(=O)NCc1cccc(F)c1Cl)[C@H](COC(=O)Nc1cc2cc(F)ccc2cn1)CC(F)(F)CN | C1CCOC1.CN(C(=O)NCc1cccc(F)c1Cl)[C@H](COC(=O)Nc1cc2cc(F)ccc2cn1)CC(F)(F)CN=[N+]=[N-].Cl.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CN(C(=O)NCc1cccc(F)c1Cl)[C@H](COC(=O)Nc1cc2cc(F)ccc2cn1)CC(F)(F)CN | US08088793B2_0842grants | 6173501d72be2b8fc05eca37582e89c3410a1198722d6ac0f5802c69 | C1CCOC1.Cl.O.[N-]=[N+]=[N:37][CH2:36][C:33]([CH2:32][C@H:15]([N:2]([CH3:1])[C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[Cl:14])[CH2:16][O:17][C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]2[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]2[cH:30][n:31]1)([F:34])[F:35].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [CH3:1][N:2]([C:3](=[O:4])[NH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]([F:12])[c:13]1[Cl:14])[C@H:15]([CH2:16][O:17][C:18](=[O:19])[NH:20][c:21]1[cH:22][c:23]2[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]2[cH:30][n:31]1)[CH2:32][C:33]([F:34])([F:35])[CH2:36][NH2:37] | ([C:1]-[NH2;D1;+0:2])>>([C:1]-[N;H0;D2;+0:2]=[N+]=[N-]) | 070a946412681dc3cde4c63e0e9dd945476d44bb1aa5127f721cc5fd | 1 | 1 | C1CCOC1.Cl.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 89 |
301,861 | 982,171 | 1,654,933 | [OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[C:3]1=[O:7] | |f:3.4.5,6.7.8| | US09108920B2_0463 | 2,015 | Br[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.C1COCCO1.CC(=O)[O-].CC(=O)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[O:1]=[C:2]1[C@@H:3]([OH:4])[CH2:5][CH2:6][NH:7]1.[Pd+2]>>[O:1]=[C:2]1[C@@H:3]([OH:4])[CH2:5][CH2:6][N:7]1[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | 0.267559 | C1COCCO1.CC(=O)[O-]~CC(=O)[O-]~[Pd+2].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.FC(F)(F)c1ccc(Br)cc1.O=C([O-])[O-]~[Cs+]~[Cs+].O=C1NCC[C@@H]1O>>O=C1[C@@H](O)CCN1c1ccc(C(F)(F)F)cc1 | C1COCCO1.CC(=O)[O-].CC(=O)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.FC(F)(F)c1ccc(Br)cc1.O=C([O-])[O-].O=C1NCC[C@@H]1O.[Cs+].[Cs+].[Pd+2]>>O=C1[C@@H](O)CCN1c1ccc(C(F)(F)F)cc1 | US09108920B2_0463grants | 5648c3f2f15e1a2e59bd6f49857f31303335f5919ec66d644f70eae3 | Br[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1.C1COCCO1.CC(=O)[O-].CC(=O)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[O:1]=[C:2]1[C@@H:3]([OH:4])[CH2:5][CH2:6][NH:7]1.[Pd+2] | [O:1]=[C:2]1[C@@H:3]([OH:4])[CH2:5][CH2:6][N:7]1[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | ([C:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7](-[C:8])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]) | 274fc64807648e92ab4ee19c6473e9c734530b7b5f51c59d812e9906 | 1 | 1 | C1COCCO1.CC(=O)[O-].CC(=O)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd+2] | 809 |
180,764 | 627,798 | 1,039,049 | [NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:16]([OH:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1 | |f:1.2,3.4| | US07858632B2_0534 | 2,010 | CO.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]([CH3:22])=[O:23].[Cl-].[NH4+].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[CH:21]([CH3:22])[OH:23] | 0.797778 | CO.COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(C)=O.[BH4-]~[Na+].[Cl-]~[NH4+]>>COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(C)O | CO.COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(C)=O.[BH4-].[Cl-].[NH4+].[Na+]>>COc1cc(C(C)C)c(Oc2cnc(N)nc2N)cc1C(C)O | US07858632B2_0534grants | 70c201fa58f6611a3f7e7e58f7f7c6fbd85298f614891fa79b33e2e6 | CO.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[C:21]([CH3:22])=[O:23].[Cl-].[NH4+].[Na+] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([CH3:7])[CH3:8])[c:9]([O:10][c:11]2[cH:12][n:13][c:14]([NH2:15])[n:16][c:17]2[NH2:18])[cH:19][c:20]1[CH:21]([CH3:22])[OH:23] | ([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-].[Cl-].[NH4+].[Na+] | 24 |
45,508 | 199,443 | 322,208 | [Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([C:17]([N:19]4[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=O)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH2:17][N:19]4[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1 | |f:1.2.3.4.5.6| | US05455246_ | 1,995 | CCOCC.O=[C:6]([N:5]1[CH2:4][CH2:3][CH:2]([OH:1])[CH2:24][CH2:23]1)[C:7]12[CH2:8][CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]31)[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]12.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][C:7]23[CH2:8][CH:9]([c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]42)[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]23)[CH2:23][CH2:24]1 | 0.928489 | CCOCC.O=C(N1CCC(O)CC1)C12CC(c3ccccc31)c1ccc(Cl)cc12.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>OC1CCN(CC23CC(c4ccccc42)c2ccc(Cl)cc23)CC1 | CCOCC.O=C(N1CCC(O)CC1)C12CC(c3ccccc31)c1ccc(Cl)cc12.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>OC1CCN(CC23CC(c4ccccc42)c2ccc(Cl)cc23)CC1 | US05455246_grants | 478d0b62a59798d32955bd4b22ca23ffb7e9be4882e6ba2d023d0e97 | CCOCC.O=[C:6]([N:5]1[CH2:4][CH2:3][CH:2]([OH:1])[CH2:24][CH2:23]1)[C:7]12[CH2:8][CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]31)[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]12.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][C:7]23[CH2:8][CH:9]([c:10]4[cH:11][cH:12][cH:13][cH:14][c:15]42)[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]23)[CH2:23][CH2:24]1 | ([#7:2]-[CH2;D2;+0:1]-[C:3])>>(O=[C;H0;D3;+0:1](-[#7:2])-[C:3]) | 164bcd5926595fb14a6a9bdfa6263711f1e81657ce47f1a9ea439ccb | 0.5 | 2 | CCOCC.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 112 |
183,682 | 636,214 | 1,052,036 | C[O:2][C:3](=[O:23])[C@@H:4]([NH:9][C:10]([NH:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6].O.[OH-].[Li+]>C1COCC1.CO.O>[C:13]12([NH:12][C:10](=[O:11])[NH:9][C@@H:4]([C:5]([CH3:7])([CH3:6])[CH3:8])[C:3]([OH:23])=[O:2])[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2 | |f:1.2.3| | US07888464B2_0596 | 2,011 | C1CCOC1.CO.C[O:22][C:20]([C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[NH:6][C:7](=[O:8])[NH:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:18]1)[CH2:19]2)=[O:21].O.O.[Li+].[OH-]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]([NH:6][C:7](=[O:8])[NH:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:18]1)[CH2:19]2)[C:20](=[O:21])[OH:22] | 0.288239 | C1CCOC1.CO.COC(=O)[C@@H](NC(=O)NC12CC3CC(CC(C3)C1)C2)C(C)(C)C.O.O~[Li+]~[OH-]>>CC(C)(C)[C@H](NC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)O | C1CCOC1.CO.COC(=O)[C@@H](NC(=O)NC12CC3CC(CC(C3)C1)C2)C(C)(C)C.O.O.[Li+].[OH-]>>CC(C)(C)[C@H](NC(=O)NC12CC3CC(CC(C3)C1)C2)C(=O)O | US07888464B2_0596grants | 8fb02e6b37cf397a7be06d91235bdc9a0769e5d0390115f04f8fe4b7 | C1CCOC1.CO.C[O:22][C:20]([C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[NH:6][C:7](=[O:8])[NH:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:18]1)[CH2:19]2)=[O:21].O.O.[Li+].[OH-] | [CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]([NH:6][C:7](=[O:8])[NH:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:18]1)[CH2:19]2)[C:20](=[O:21])[OH:22] | ([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 | C1CCOC1.CO.O.O.[Li+].[OH-] | 88 |
295,879 | 963,586 | 1,621,176 | [NH2:1][CH2:2][CH2:3][N:4]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1F)[C:25]#[N:26].CCN(C(C)C)C(C)C.O>CS(C)=O>[C:25]([C:24]1[CH:27]=[CH:28][C:29]([NH:1][CH2:2][CH2:3][N:4]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)(=[O:7])=[O:6])=[C:22]([F:21])[CH:23]=1)#[N:26] | null | US09040563B2_0121 | 2,015 | CCN(C(C)C)C(C)C.CS(C)=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][c:27]1[F:28].O.[NH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][n:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][N:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[c:27]([F:28])[cH:29]1 | 0.510959 | CCN(C(C)C)C(C)C.CS(C)=O.N#Cc1ccc(F)c(F)c1.NCCN(CC1CCCCC1)S(=O)(=O)c1ccccn1.O>>N#Cc1ccc(NCCN(CC2CCCCC2)S(=O)(=O)c2ccccn2)c(F)c1 | CCN(C(C)C)C(C)C.CS(C)=O.N#Cc1ccc(F)c(F)c1.NCCN(CC1CCCCC1)S(=O)(=O)c1ccccn1.O>>N#Cc1ccc(NCCN(CC2CCCCC2)S(=O)(=O)c2ccccn2)c(F)c1 | US09040563B2_0121grants | ec0e65abfb5b837cfbfb7055fc00a6f8908984194b76263f3c42702b | CCN(C(C)C)C(C)C.CS(C)=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][c:27]1[F:28].O.[NH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][cH:25][n:26]1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][N:10]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[c:27]([F:28])[cH:29]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.CS(C)=O.O | 572 |
1,732 | 9,229 | 10,686 | [C:1]([C:4]1[CH:26]=[CH:25][C:7]([NH:8][C:9]2[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[N+:22]([O-])=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].N(C1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1[N+]([O-])=O)C1C=CC=CC=1>>[NH2:22][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])[C:9]=1[NH:8][C:7]1[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:26][CH:25]=1)[C:13]([OH:15])=[O:14] | null | US03971819_ | 1,976 | NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccccc1.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]([S:10]([NH2:11])(=[O:12])=[O:13])[c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1>>[NH2:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]([S:10]([NH2:11])(=[O:12])=[O:13])[c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1 | 0.307097 | NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccc(C(=O)O)cc1.NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccccc1>>Nc1cc(C(=O)O)cc(S(N)(=O)=O)c1Nc1ccc(C(=O)O)cc1 | NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccc(C(=O)O)cc1.NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccccc1>>Nc1cc(C(=O)O)cc(S(N)(=O)=O)c1Nc1ccc(C(=O)O)cc1 | US03971819_grants | fce334993af9005d56b76bc32456694538a54ebb96705689876875ce | NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccccc1.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]([S:10]([NH2:11])(=[O:12])=[O:13])[c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1 | [NH2:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][c:9]([S:10]([NH2:11])(=[O:12])=[O:13])[c:14]1[NH:15][c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | NS(=O)(=O)c1cc(C(=O)O)cc([N+](=O)[O-])c1Nc1ccccc1 | 1 |
362,439 | 650,069 | null | Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([I:30])=[CH:7][CH:8]=2)[N:3]=1.[CH3:31][NH:32][CH3:33]>C1COCC1>[CH3:31][N:32]([CH3:33])[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:18][CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]([I:30])=[CH:7][CH:8]=2)[N:3]=1 | null | US20090004185A1_0456 | 2,009 | C1CCOC1.Cl[c:4]1[n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][c:28]([I:29])[cH:30][c:31]2[n:32]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][c:28]([I:29])[cH:30][c:31]2[n:32]1 | 0.803155 | C1CCOC1.CNC.O=C(Nc1ccc(CNc2nc(Cl)nc3cc(I)ccc23)cc1)c1ccc(F)cc1>>CN(C)c1nc(NCc2ccc(NC(=O)c3ccc(F)cc3)cc2)c2ccc(I)cc2n1 | C1CCOC1.CNC.O=C(Nc1ccc(CNc2nc(Cl)nc3cc(I)ccc23)cc1)c1ccc(F)cc1>>CN(C)c1nc(NCc2ccc(NC(=O)c3ccc(F)cc3)cc2)c2ccc(I)cc2n1 | US20090004185A1_0456apps | 240c7276185d9de073e9c6899216c4b33495bb5151572882b92a8de5 | C1CCOC1.Cl[c:4]1[n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][c:28]([I:29])[cH:30][c:31]2[n:32]1.[CH3:1][NH:2][CH3:3] | [CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][c:28]([I:29])[cH:30][c:31]2[n:32]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | b57905a5bce8517a4e40b0e20794e889407f66a0ae3d7a09e7fbb00e | 1 | 1 | C1CCOC1 | 36 |
398,411 | 1,327,027 | null | [N:1]1([C:5]2[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])OC3C=CC=CC=3)=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O.O>[N:1]1([C:5]2[N:10]=[CH:9][C:8]([NH:11][C:12]([NH:35][CH2:34][C:33]3[C:28]([N:25]4[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]4)=[N:29][C:30]([C:36]([F:39])([F:37])[F:38])=[CH:31][CH:32]=3)=[O:20])=[CH:7][CH:6]=2)[CH2:2][CH2:3][CH2:4]1 | null | US20130029961A1_0781 | 2,013 | CCN(CC)CC.CS(C)=O.O.[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[CH2:16][NH2:17])[CH2:31][CH2:32]1.c1ccc(O[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][c:24]([N:25]3[CH2:26][CH2:27][CH2:28]3)[n:29][cH:30]2)cc1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[CH2:16][NH:17][C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][c:24]([N:25]3[CH2:26][CH2:27][CH2:28]3)[n:29][cH:30]2)[CH2:31][CH2:32]1 | 0.286893 | CC1CCN(c2nc(C(F)(F)F)ccc2CN)CC1.CCN(CC)CC.CS(C)=O.O.O=C(Nc1ccc(N2CCC2)nc1)Oc1ccccc1>>CC1CCN(c2nc(C(F)(F)F)ccc2CNC(=O)Nc2ccc(N3CCC3)nc2)CC1 | CC1CCN(c2nc(C(F)(F)F)ccc2CN)CC1.CCN(CC)CC.CS(C)=O.O.O=C(Nc1ccc(N2CCC2)nc1)Oc1ccccc1>>CC1CCN(c2nc(C(F)(F)F)ccc2CNC(=O)Nc2ccc(N3CCC3)nc2)CC1 | US20130029961A1_0781apps | 46cb28a3f1d408344561d5d28ae30e4b2a958e74b3e343833b394557 | CCN(CC)CC.CS(C)=O.O.[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[CH2:16][NH2:17])[CH2:31][CH2:32]1.c1ccc(O[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][c:24]([N:25]3[CH2:26][CH2:27][CH2:28]3)[n:29][cH:30]2)cc1 | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[CH2:16][NH:17][C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][c:24]([N:25]3[CH2:26][CH2:27][CH2:28]3)[n:29][cH:30]2)[CH2:31][CH2:32]1 | ([#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 | CCN(CC)CC.CS(C)=O.O | 488 |
288,398 | 939,981 | 1,576,847 | C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)=[CH:19][C:18]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:20]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)=[CH:19][C:18]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:17][N:16]=2)[CH2:13][CH2:14]1 | null | US08952004B2_0240 | 2,015 | CC(C)(C)OC(=O)[NH:14][CH2:13][CH:12]1[CH2:11][CH2:10][N:9]([c:8]2[n:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:28][c:17]2[NH:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:16][CH2:15]1.ClCCl.O=C(O)C(F)(F)F>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][n:7][c:8]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:13][NH2:14])[CH2:15][CH2:16]2)[c:17]([NH:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[cH:28]1 | 0.558772 | CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2NC(=O)c2cccc(Cl)c2)CC1.ClCCl.O=C(O)C(F)(F)F>>CS(=O)(=O)c1cnc(N2CCC(CN)CC2)c(NC(=O)c2cccc(Cl)c2)c1 | CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2NC(=O)c2cccc(Cl)c2)CC1.ClCCl.O=C(O)C(F)(F)F>>CS(=O)(=O)c1cnc(N2CCC(CN)CC2)c(NC(=O)c2cccc(Cl)c2)c1 | US08952004B2_0240grants | 34a390df04f1b11a4d0d6ec2334bbcc82aa2c468099cb7852692632c | CC(C)(C)OC(=O)[NH:14][CH2:13][CH:12]1[CH2:11][CH2:10][N:9]([c:8]2[n:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:28][c:17]2[NH:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:16][CH2:15]1.ClCCl.O=C(O)C(F)(F)F | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][n:7][c:8]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:13][NH2:14])[CH2:15][CH2:16]2)[c:17]([NH:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[cH:28]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 |
154,107 | 548,805 | 918,148 | [Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:12][CH3:13] | |f:1.2.3.4.5.6| | US07576218B2_0188 | 2,009 | C1CCOC1.CO[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9][cH:8]1)=[O:7].ClCCl.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][cH:9][c:10]1[Cl:11] | 0.828209 | C1CCOC1.COC(=O)c1ccc(Cl)c(OC)c1.ClCCl.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>COc1cc(CO)ccc1Cl | C1CCOC1.COC(=O)c1ccc(Cl)c(OC)c1.ClCCl.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>COc1cc(CO)ccc1Cl | US07576218B2_0188grants | 41ec44f3a936815f01ea71093680b7caa87ec880c649615160c8dfb2 | C1CCOC1.CO[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9][cH:8]1)=[O:7].ClCCl.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][cH:9][c:10]1[Cl:11] | ([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.ClCCl.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 444 |
431,943 | 1,852,886 | null | [F:1][C:2]([F:15])([C:5]1[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=1)[CH2:3][OH:4].CCN(C(C)C)C(C)C.[O:25](S(C(F)(F)F)(=O)=O)[S:26]([C:29]([F:32])([F:31])[F:30])(=O)=[O:27]>CCOCC>[F:30][C:29]([F:32])([F:31])[S:26]([O:4][CH2:3][C:2]([F:1])([F:15])[C:5]1[CH:6]=[N:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1)(=[O:27])=[O:25] | null | US20160075713A1_0693 | 2,016 | CCN(C(C)C)C(C)C.CCOCC.O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:19]([F:20])([F:21])[F:22])C(F)(F)F.[OH:4][CH2:5][C:6]([F:7])([F:8])[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[n:17][cH:18]1>>[O:1]=[S:2](=[O:3])([O:4][CH2:5][C:6]([F:7])([F:8])[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[n:17][cH:18]1)[C:19]([F:20])([F:21])[F:22] | 0.024204 | CCN(C(C)C)C(C)C.CCOCC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.OCC(F)(F)c1ccc(C(F)(F)F)nc1>>O=S(=O)(OCC(F)(F)c1ccc(C(F)(F)F)nc1)C(F)(F)F | CCN(C(C)C)C(C)C.CCOCC.O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.OCC(F)(F)c1ccc(C(F)(F)F)nc1>>O=S(=O)(OCC(F)(F)c1ccc(C(F)(F)F)nc1)C(F)(F)F | US20160075713A1_0693apps | 72a94427c0cf357d4f6d50fcf21708e4a9b06ff88e859a4bc04cb186 | CCN(C(C)C)C(C)C.CCOCC.O=S(=O)(O[S:2](=[O:1])(=[O:3])[C:19]([F:20])([F:21])[F:22])C(F)(F)F.[OH:4][CH2:5][C:6]([F:7])([F:8])[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[n:17][cH:18]1 | [O:1]=[S:2](=[O:3])([O:4][CH2:5][C:6]([F:7])([F:8])[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[n:17][cH:18]1)[C:19]([F:20])([F:21])[F:22] | ([C:8]-[O;H0;D2;+0:9]-[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])>>(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]).([C:8]-[OH;D1;+0:9]) | 6e603a4201f805322ef8e72ed565f5eb1da15aaf0f92d9ca21dc8767 | 1 | 1 | CCN(C(C)C)C(C)C.CCOCC | 582 |
314,240 | 1,021,588 | 1,729,416 | [O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH2:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH:30][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1 | |f:1.2,3.4| | US09266832B2_0978 | 2,016 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[NH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]12>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]12)[c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1 | 0.873471 | CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.Cl~NCCc1c[nH]c2ccc(Cl)cc12.O=C(O)c1ccc(Oc2ccccc2)cc1>>O=C(NCCc1c[nH]c2ccc(Cl)cc12)c1ccc(Oc2ccccc2)cc1 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.NCCc1c[nH]c2ccc(Cl)cc12.O=C(O)c1ccc(Oc2ccccc2)cc1>>O=C(NCCc1c[nH]c2ccc(Cl)cc12)c1ccc(Oc2ccccc2)cc1 | US09266832B2_0978grants | 655b96682a30e12fa9c9f2e9b59da83e154e0a25f5d8a70884c094fd | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1.[NH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]12 | [O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]12)[c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]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 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F | 334 |
210,199 | 711,167 | 1,171,512 | [NH2:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[F:18][C:19]([F:33])([F:32])[C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH:23]=O.O>CO>[F:18][C:19]([F:32])([F:33])[C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:27]=1)[CH2:23][NH:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4] | null | US08148427B2_0073 | 2,012 | CO.O.O=[CH:4][c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1.[CH3:1][C@H:2]([NH2:3])[C@H:19]([OH:20])[c:21]1[cH:22][cH:23][c:24]([OH:25])[c:26]([NH:27][S:28]([CH3:29])(=[O:30])=[O:31])[cH:32]1>>[CH3:1][C@H:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)[C@H:19]([OH:20])[c:21]1[cH:22][cH:23][c:24]([OH:25])[c:26]([NH:27][S:28]([CH3:29])(=[O:30])=[O:31])[cH:32]1 | 0.065152 | CO.C[C@H](N)[C@H](O)c1ccc(O)c(NS(C)(=O)=O)c1.O.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>C[C@H](NCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)[C@H](O)c1ccc(O)c(NS(C)(=O)=O)c1 | CO.C[C@H](N)[C@H](O)c1ccc(O)c(NS(C)(=O)=O)c1.O.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>C[C@H](NCc1cc(C(F)(F)F)cc(C(F)(F)F)c1)[C@H](O)c1ccc(O)c(NS(C)(=O)=O)c1 | US08148427B2_0073grants | cddd6200af5c67547a2d62c810b79430aa4b862cd890069e3c6bd8c6 | CO.O.O=[CH:4][c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1.[CH3:1][C@H:2]([NH2:3])[C@H:19]([OH:20])[c:21]1[cH:22][cH:23][c:24]([OH:25])[c:26]([NH:27][S:28]([CH3:29])(=[O:30])=[O:31])[cH:32]1 | [CH3:1][C@H:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1)[C@H:19]([OH:20])[c:21]1[cH:22][cH:23][c:24]([OH:25])[c:26]([NH:27][S:28]([CH3:29])(=[O:30])=[O:31])[cH:32]1 | ([C:3]-[NH;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C:3]-[NH2;D1;+0:4]) | f78624bd87f224b709b14a27d6ee712af84642974d7873cf47c74b30 | 1 | 1 | CO.O | 468 |
79,839 | 323,143 | 547,318 | [NH2:1][CH:2]([C:11]1[O:15][C:14]([NH2:16])=[N:13][N:12]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32](O)=[O:33])=[CH:31][C:25]=3[N:24]=2)=[CH:19][CH:18]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(NC(C)C)(C)C>CN(C)C=O>[NH2:16][C:14]1[O:15][C:11]([CH:2]([NH:1][C:32]([C:30]2[CH:29]=[CH:28][C:26]3[NH:27][C:23]([C:20]4[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=4)=[N:24][C:25]=3[CH:31]=2)=[O:33])[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:12][N:13]=1 | |f:2.3| | US06358978B1_ | 2,002 | CC(C)NC(C)C.CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F.O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]2[nH:22][c:23](-[c:24]3[cH:25][cH:26][n:27][cH:28][cH:29]3)[n:30][c:31]2[cH:32]1.[NH2:1][c:2]1[n:3][n:4][c:5]([CH:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH2:15])[o:33]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([CH:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15][C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]3[nH:22][c:23](-[c:24]4[cH:25][cH:26][n:27][cH:28][cH:29]4)[n:30][c:31]3[cH:32]2)[o:33]1 | 0.775309 | CC(C)NC(C)C.CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C~F[B-](F)(F)F.CN(C)C=O.Nc1nnc(C(N)CCc2ccccc2)o1.O=C(O)c1ccc2[nH]c(-c3ccncc3)nc2c1>>Nc1nnc(C(CCc2ccccc2)NC(=O)c2ccc3[nH]c(-c4ccncc4)nc3c2)o1 | CC(C)NC(C)C.CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F.Nc1nnc(C(N)CCc2ccccc2)o1.O=C(O)c1ccc2[nH]c(-c3ccncc3)nc2c1>>Nc1nnc(C(CCc2ccccc2)NC(=O)c2ccc3[nH]c(-c4ccncc4)nc3c2)o1 | US06358978B1_grants | 9e262888693c510c5905f5f209f9e2f16875bddde781adf53d09ee5a | CC(C)NC(C)C.CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F.O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]2[nH:22][c:23](-[c:24]3[cH:25][cH:26][n:27][cH:28][cH:29]3)[n:30][c:31]2[cH:32]1.[NH2:1][c:2]1[n:3][n:4][c:5]([CH:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH2:15])[o:33]1 | [NH2:1][c:2]1[n:3][n:4][c:5]([CH:6]([CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15][C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]3[nH:22][c:23](-[c:24]4[cH:25][cH:26][n:27][cH:28][cH:29]4)[n:30][c:31]3[cH:32]2)[o:33]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 | CC(C)NC(C)C.CCOC(=O)C(C#N)=NOC(N(C)C)=[N+](C)C.CN(C)C=O.F[B-](F)(F)F | 334 |
264,176 | 870,170 | 1,448,799 | [CH2:1]([NH2:4])[CH2:2][CH3:3].C[Al](C)C.[CH2:9]([C:12]1[N:13]([CH2:25][CH2:26][CH2:27][C:28](OCC)=[O:29])[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=1)[CH2:10][CH3:11]>ClCCl.C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:13]1[C:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:24]=[C:12]1[CH2:9][CH2:10][CH3:11])[CH2:2][CH3:3] | null | US08697873B2_0796 | 2,014 | CCO[C:5](=[O:6])[CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH2:12][CH2:13][CH3:14])[n:15][c:16]2[cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]12.C[Al](C)C.Cc1ccccc1.ClCCl.[CH3:1][CH2:2][CH2:3][NH2:4]>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH2:12][CH2:13][CH3:14])[n:15][c:16]2[cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]12 | 0.979036 | CCCN.CCCc1nc2cnc3ccccc3c2n1CCCC(=O)OCC.C[Al](C)C.Cc1ccccc1.ClCCl>>CCCNC(=O)CCCn1c(CCC)nc2cnc3ccccc3c21 | CCCN.CCCc1nc2cnc3ccccc3c2n1CCCC(=O)OCC.C[Al](C)C.Cc1ccccc1.ClCCl>>CCCNC(=O)CCCn1c(CCC)nc2cnc3ccccc3c21 | US08697873B2_0796grants | 5dbb5b5e330b3d5b050ae1bce85a70a12e3cfbab2f1b97ba056ce433 | CCO[C:5](=[O:6])[CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH2:12][CH2:13][CH3:14])[n:15][c:16]2[cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]12.C[Al](C)C.Cc1ccccc1.ClCCl.[CH3:1][CH2:2][CH2:3][NH2:4] | [CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][CH2:8][CH2:9][n:10]1[c:11]([CH2:12][CH2:13][CH3:14])[n:15][c:16]2[cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]12 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(C-C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 9731dcd789df0a55995eab09da9719d520c439d74b195b7e7bb6c118 | 1 | 1 | C[Al](C)C.Cc1ccccc1.ClCCl | 64 |
81,693 | 329,218 | 559,734 | [N:1]([CH2:4][C@H:5]([OH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3].C(N(CC)CC)C.[O:20]1CC[CH2:22][CH2:21]1.C(Cl)(=O)C>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[N:1]([CH2:4][C@H:5]([O:12][C:21](=[O:20])[CH3:22])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:2]=[N-:3] | |f:5.6| | US06403804B1_ | 2,002 | C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.Cl[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]([CH2:8][N:9]=[N+:10]=[N-:11])[OH:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]([CH2:8][N:9]=[N+:10]=[N-:11])[O:12][C:13]([CH3:14])=[O:15] | 0.945712 | C1CCOC1.CC(=O)Cl.CCCCCC~CCOC(C)=O.CCN(CC)CC.CCOC(=O)C[C@@H](O)CN=[N+]=[N-].CN(C)c1ccncc1>>CCOC(=O)C[C@H](CN=[N+]=[N-])OC(C)=O | C1CCOC1.CC(=O)Cl.CCCCCC.CCN(CC)CC.CCOC(=O)C[C@@H](O)CN=[N+]=[N-].CCOC(C)=O.CN(C)c1ccncc1>>CCOC(=O)C[C@H](CN=[N+]=[N-])OC(C)=O | US06403804B1_grants | 017acc5bd347615782efda97787233b29ef4eec02d88b5d1800c951c | C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1.Cl[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]([CH2:8][N:9]=[N+:10]=[N-:11])[OH:12] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]([CH2:8][N:9]=[N+:10]=[N-:11])[O:12][C:13]([CH3:14])=[O:15] | ([C:4]-[O;H0;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]-[OH;D1;+0:5]) | dd95e42df91c7014b8bb61b2fcc1694968b310b2018cb51dbcc5f881 | 1 | 1 | C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.CN(C)c1ccncc1 | 126 |
278,748 | 913,317 | 1,527,039 | [CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][N:11]=[C:5]2[N:4]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:3]1=[O:24].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:33]1([C:30]2[CH:31]=[CH:32][C:27]([CH2:26][N:10]3[C:9]([S:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:6]4[C:5]([N:4]([CH2:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:3](=[O:24])[N:2]([CH3:1])[C:7]4=[O:8])=[N:11]3)=[CH:28][CH:29]=2)[CH:37]=[N:36][CH:35]=[N:34]1 | |f:2.3.4| | US08859564B2_0441 | 2,014 | Br[CH2:15][c:16]1[cH:17][cH:18][c:19](-[n:20]2[cH:21][n:22][cH:23][n:24]2)[cH:25][cH:26]1.CN(C)C=O.O=C([O-])[O-].[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([S:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[nH:14][n:27][c:28]2[n:29]([CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]1=[O:36].[K+].[K+]>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([S:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19](-[n:20]4[cH:21][n:22][cH:23][n:24]4)[cH:25][cH:26]3)[n:27][c:28]2[n:29]([CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]1=[O:36] | 0.538053 | BrCc1ccc(-n2cncn2)cc1.CN(C)C=O.Cn1c(=O)c2c(Sc3ccccc3)[nH]nc2n(CC(C)(C)C)c1=O.O=C([O-])[O-]~[K+]~[K+]>>Cn1c(=O)c2c(Sc3ccccc3)n(Cc3ccc(-n4cncn4)cc3)nc2n(CC(C)(C)C)c1=O | BrCc1ccc(-n2cncn2)cc1.CN(C)C=O.Cn1c(=O)c2c(Sc3ccccc3)[nH]nc2n(CC(C)(C)C)c1=O.O=C([O-])[O-].[K+].[K+]>>Cn1c(=O)c2c(Sc3ccccc3)n(Cc3ccc(-n4cncn4)cc3)nc2n(CC(C)(C)C)c1=O | US08859564B2_0441grants | bb00fb68b8d5c273369d682316e7434a702d3f9e620a521ecc7771c5 | Br[CH2:15][c:16]1[cH:17][cH:18][c:19](-[n:20]2[cH:21][n:22][cH:23][n:24]2)[cH:25][cH:26]1.CN(C)C=O.O=C([O-])[O-].[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([S:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[nH:14][n:27][c:28]2[n:29]([CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]1=[O:36].[K+].[K+] | [CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([S:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19](-[n:20]4[cH:21][n:22][cH:23][n:24]4)[cH:25][cH:26]3)[n:27][c:28]2[n:29]([CH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]1=[O:36] | ([#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 | CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 635 |
342,716 | 354,212 | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=2[O:23][CH2:24][C:25](=[O:28])[NH:26][CH3:27])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([NH:33][CH2:32][CH2:31][O:30][CH3:29])=[O:9])[CH:5]=[C:4]([CH:3]=1)[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=1[O:23][CH2:24][C:25](=[O:28])[NH:26][CH3:27])=[O:12] | null | US20060116410A1_0413 | 2,006 | O[C:25]([c:24]1[cH:23][c:21]([Cl:22])[cH:20][c:19]([C:17]([NH:16][CH2:15][c:14]2[c:7]([O:6][CH2:5][C:3]([NH:2][CH3:1])=[O:4])[cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]2)=[O:18])[cH:32]1)=[O:26].[NH2:27][CH2:28][CH2:29][O:30][CH3:31]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]1[CH2:15][NH:16][C:17](=[O:18])[c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]([C:25](=[O:26])[NH:27][CH2:28][CH2:29][O:30][CH3:31])[cH:32]1 | 0.959662 | CNC(=O)COc1cc(C#N)ccc1CNC(=O)c1cc(Cl)cc(C(=O)O)c1.COCCN>>CNC(=O)COc1cc(C#N)ccc1CNC(=O)c1cc(Cl)cc(C(=O)NCCOC)c1 | CNC(=O)COc1cc(C#N)ccc1CNC(=O)c1cc(Cl)cc(C(=O)O)c1.COCCN>>CNC(=O)COc1cc(C#N)ccc1CNC(=O)c1cc(Cl)cc(C(=O)NCCOC)c1 | US20060116410A1_0413apps | 9ced8e6ff291425a9bfadf85e1a3eb2011730652ae071004cc6a9e34 | O[C:25]([c:24]1[cH:23][c:21]([Cl:22])[cH:20][c:19]([C:17]([NH:16][CH2:15][c:14]2[c:7]([O:6][CH2:5][C:3]([NH:2][CH3:1])=[O:4])[cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13]2)=[O:18])[cH:32]1)=[O:26].[NH2:27][CH2:28][CH2:29][O:30][CH3:31] | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]1[CH2:15][NH:16][C:17](=[O:18])[c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]([C:25](=[O:26])[NH:27][CH2:28][CH2:29][O:30][CH3:31])[cH:32]1 | ([#7:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[c:6]:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]):[c:11]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7](-[C:8](-[#7:9])=[O;D1;H0:10]):[c:11]:1).([C:12]-[NH2;D1;+0:13]) | 191d46f586817f8eaa5e009505667a0f7ca97688b07e4c37d143e1ed | 0.5 | 2 | null | 836 |
282,542 | 925,160 | 1,548,803 | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:18][CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)[CH:3]=1 | |f:2.3.4| | US08906900B2_0616 | 2,014 | CN(C)C=O.F[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][c:7]([Br:8])[cH:9]1.O.O=C([O-])[O-].[K+].[K+].[NH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[NH:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | 0.960385 | CN(C)C=O.NC1CCOCC1.O.O=C([O-])[O-]~[K+]~[K+].O=[N+]([O-])c1ccc(Br)cc1F>>O=[N+]([O-])c1ccc(Br)cc1NC1CCOCC1 | CN(C)C=O.NC1CCOCC1.O.O=C([O-])[O-].O=[N+]([O-])c1ccc(Br)cc1F.[K+].[K+]>>O=[N+]([O-])c1ccc(Br)cc1NC1CCOCC1 | US08906900B2_0616grants | e1dce5bcfb522cd255467777550b051d3be6a1c622bbf171ad9f9f3c | CN(C)C=O.F[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][c:7]([Br:8])[cH:9]1.O.O=C([O-])[O-].[K+].[K+].[NH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[NH:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]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 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 572 |
136,417 | 494,628 | 833,344 | C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH2:24][C:25]2[N:26]=[C:27]([NH:30][C:31](=[O:39])[C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[S:28][CH:29]=2)=[O:23])=[C:17]([F:40])[CH:16]=1)(=[O:8])=[O:7])(C)(C)C.Cl>C(Cl)(Cl)Cl.CO>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([C:31]([NH:30][C:27]2[S:28][CH:29]=[C:25]([CH2:24][C:22](=[O:23])[NH:21][C:18]3[CH:19]=[CH:20][C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:6](=[O:7])(=[O:8])[NH2:5])=[CH:16][C:17]=3[F:40])[N:26]=2)=[O:39])=[CH:37][CH:36]=1 | |f:2.3| | US07361672B2_0232 | 2,008 | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[CH2:18][c:19]2[cH:20][s:21][c:22]([NH:23][C:24](=[O:25])[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[n:33]2)[c:34]([F:35])[cH:36]1.CO.Cl.ClC(Cl)Cl>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[CH2:18][c:19]2[cH:20][s:21][c:22]([NH:23][C:24](=[O:25])[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[n:33]2)[c:34]([F:35])[cH:36]1 | 0.505158 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(NC(=O)Cc2csc(NC(=O)c3ccc(Cl)cc3)n2)c(F)c1.CO~ClC(Cl)Cl.Cl>>NS(=O)(=O)c1ccccc1-c1ccc(NC(=O)Cc2csc(NC(=O)c3ccc(Cl)cc3)n2)c(F)c1 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(NC(=O)Cc2csc(NC(=O)c3ccc(Cl)cc3)n2)c(F)c1.CO.Cl.ClC(Cl)Cl>>NS(=O)(=O)c1ccccc1-c1ccc(NC(=O)Cc2csc(NC(=O)c3ccc(Cl)cc3)n2)c(F)c1 | US07361672B2_0232grants | b5385f897aa57b96c883053ced3c85047475d3a040080b7e0df28b07 | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[CH2:18][c:19]2[cH:20][s:21][c:22]([NH:23][C:24](=[O:25])[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[n:33]2)[c:34]([F:35])[cH:36]1.CO.Cl.ClC(Cl)Cl | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[CH2:18][c:19]2[cH:20][s:21][c:22]([NH:23][C:24](=[O:25])[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[n:33]2)[c:34]([F:35])[cH:36]1 | ([NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5])>>(C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]) | b6b8910b5a5ba9c7b8841e8bf1b60369c43b8bd72c6c9540ecfceb20 | 1 | 1 | CO.Cl.ClC(Cl)Cl | 680 |
383,169 | 982,748 | null | [C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([C:23](O)=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH:60]1[CH2:65][CH2:64][CH:63]([CH2:66][C:67]([O:69][CH3:70])=[O:68])[CH2:62][CH2:61]1>CN(C=O)C>[CH3:70][O:69][C:67](=[O:68])[CH2:66][CH:63]1[CH2:64][CH2:65][N:60]([C:23]([C:21]2[CH:20]=[CH:19][C:8]3[N:9]([CH2:10][CH:11]4[CH2:16][CH2:15][C:14]([F:17])([F:18])[CH2:13][CH2:12]4)[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][C:7]=3[CH:22]=2)=[O:24])[CH2:61][CH2:62]1 | |f:2.3,4.5| | US20100305140A1_0228 | 2,010 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[n:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]2[CH2:25][CH:26]1[CH2:27][CH2:28][C:29]([F:30])([F:31])[CH2:32][CH2:33]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:34][CH2:35]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[n:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]3[CH2:25][CH:26]2[CH2:27][CH2:28][C:29]([F:30])([F:31])[CH2:32][CH2:33]2)[CH2:34][CH2:35]1 | 0.297817 | CC(C)(C)c1nc2cc(C(=O)O)ccc2n1CC1CCC(F)(F)CC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.COC(=O)CC1CCNCC1~Cl>>COC(=O)CC1CCN(C(=O)c2ccc3c(c2)nc(C(C)(C)C)n3CC2CCC(F)(F)CC2)CC1 | CC(C)(C)c1nc2cc(C(=O)O)ccc2n1CC1CCC(F)(F)CC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.COC(=O)CC1CCNCC1.Cl.F[P-](F)(F)(F)(F)F>>COC(=O)CC1CCN(C(=O)c2ccc3c(c2)nc(C(C)(C)C)n3CC2CCC(F)(F)CC2)CC1 | US20100305140A1_0228apps | fa1cfe0ee2b78183786bf979f795ba9564e487929ba770f83346ece7 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[n:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]2[CH2:25][CH:26]1[CH2:27][CH2:28][C:29]([F:30])([F:31])[CH2:32][CH2:33]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:34][CH2:35]1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[n:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]3[CH2:25][CH:26]2[CH2:27][CH2:28][C:29]([F:30])([F:31])[CH2:32][CH2:33]2)[CH2:34][CH2:35]1 | ([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(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F | 44 |
97,593 | 377,827 | 646,802 | C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)([OH:4])=[O:2] | |f:1.2| | US06727250B2_ | 2,004 | CO.C[O:23][C:21]([c:20]1[c:15]([NH:14][C:2](=[O:1])/[CH:3]=[CH:4]/[c:5]2[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]2)[cH:16][cH:17][cH:18][cH:19]1)=[O:22].[Na+].[OH-]>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1)[NH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[C:21](=[O:22])[OH:23] | 0.949071 | CO.COC(=O)c1ccccc1NC(=O)/C=C/c1cccc([N+](=O)[O-])c1.[Na+]~[OH-]>>O=C(/C=C/c1cccc([N+](=O)[O-])c1)Nc1ccccc1C(=O)O | CO.COC(=O)c1ccccc1NC(=O)/C=C/c1cccc([N+](=O)[O-])c1.[Na+].[OH-]>>O=C(/C=C/c1cccc([N+](=O)[O-])c1)Nc1ccccc1C(=O)O | US06727250B2_grants | 765ff8e58e0a77a3e008e8198840380011a1937f8d4caa398bb6f3be | CO.C[O:23][C:21]([c:20]1[c:15]([NH:14][C:2](=[O:1])/[CH:3]=[CH:4]/[c:5]2[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]2)[cH:16][cH:17][cH:18][cH:19]1)=[O:22].[Na+].[OH-] | [O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1)[NH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[C:21](=[O:22])[OH:23] | ([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.[Na+].[OH-] | 247 |
68,103 | 283,735 | 481,182 | [Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][NH:11][CH2:12][CH2:13][OH:14]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:9])[CH:5]=[C:6]([N:11]([CH2:12][CH2:13][OH:14])[CH3:10])[N:7]=1 | null | US06107301_ | 2,000 | CCO.Cl[c:4]1[cH:3][c:2]([CH3:1])[n:13][c:11]([Cl:12])[n:10]1.[NH:5]([CH3:6])[CH2:7][CH2:8][OH:9]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]([CH3:6])[CH2:7][CH2:8][OH:9])[n:10][c:11]([Cl:12])[n:13]1 | 0.987629 | CCO.CNCCO.Cc1cc(Cl)nc(Cl)n1>>Cc1cc(N(C)CCO)nc(Cl)n1 | CCO.CNCCO.Cc1cc(Cl)nc(Cl)n1>>Cc1cc(N(C)CCO)nc(Cl)n1 | US06107301_grants | bd5aad79cf4f711203bd33eb0fe26acc11165cf83c603e1c35b0baa5 | CCO.Cl[c:4]1[cH:3][c:2]([CH3:1])[n:13][c:11]([Cl:12])[n:10]1.[NH:5]([CH3:6])[CH2:7][CH2:8][OH:9] | [CH3:1][c:2]1[cH:3][c:4]([N:5]([CH3:6])[CH2:7][CH2:8][OH:9])[n:10][c:11]([Cl:12])[n:13]1 | ([C:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[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]-[NH;D2;+0:8]-[C;D1;H3:9]) | 8f98bb24369a55acd3cc9dff894309cce726b36a5b61365d2720fb76 | 1 | 1 | CCO | 162 |
275,804 | 904,694 | 1,509,187 | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([CH2:15][OH:16])[O:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[C:13]([CH2:15][OH:16])[O:12][N:11]=2)=[CH:8][CH:9]=1 | null | US08828992B2_0244 | 2,014 | CCO.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[o:11][n:12]2)[cH:13][cH:14]1.[H][H].[Pd]>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[o:11][n:12]2)[cH:13][cH:14]1 | 0.968465 | CCO.O=[N+]([O-])c1ccc(-c2cc(CO)on2)cc1.[H][H].[Pd]>>Nc1ccc(-c2cc(CO)on2)cc1 | CCO.O=[N+]([O-])c1ccc(-c2cc(CO)on2)cc1.[H][H].[Pd]>>Nc1ccc(-c2cc(CO)on2)cc1 | US08828992B2_0244grants | fffaf39df0ed5e04d60d7e1c8ce31683415ca23e52641424a0423c7a | CCO.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[o:11][n:12]2)[cH:13][cH:14]1.[H][H].[Pd] | [NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[o:11][n:12]2)[cH:13][cH:14]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.[H][H].[Pd] | 1 |
105,524 | 402,162 | 686,703 | [N:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:19])[CH:11]=[CH:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[S:30]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][NH:9][C:10](=[O:19])[CH:11]=[CH:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:2][CH2:3]1)(=[O:31])=[O:32] | null | US06903118B1_0566 | 2,005 | ClCCl.Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[cH:30]1.[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][NH:17][CH2:31][CH2:32]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3[cH:30]2)[CH2:31][CH2:32]1 | 0.726838 | ClCCl.O=C(C=Cc1cccnc1)NCCN1CCNCC1.O=S(=O)(Cl)c1ccc2ccccc2c1>>O=C(C=Cc1cccnc1)NCCN1CCN(S(=O)(=O)c2ccc3ccccc3c2)CC1 | ClCCl.O=C(C=Cc1cccnc1)NCCN1CCNCC1.O=S(=O)(Cl)c1ccc2ccccc2c1>>O=C(C=Cc1cccnc1)NCCN1CCN(S(=O)(=O)c2ccc3ccccc3c2)CC1 | US06903118B1_0566grants | 16f454ef6440d66628ceef8c545d0178ee1d46cb11fb25caaf1cc979 | ClCCl.Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[cH:30]1.[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][NH:17][CH2:31][CH2:32]1 | [O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3[cH:30]2)[CH2:31][CH2:32]1 | ([C:5]-[N;H0;D3;+0:6](-[C:7])-[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]-[NH;D2;+0:6]-[C:7]) | 1c3a913f221c79d5ab4e40f13ae7431f2711f9942a72ad3fc8bf5434 | 1 | 1 | ClCCl | 99 |
95,627 | 371,529 | 634,546 | C1(NC(N)=S)C=CC=CC=1.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([S:29]([NH:32][CH:33]2[CH2:37][CH2:36][O:35][NH:34]2)(=[O:31])=[O:30])[C:23]=1[OH:38])=[S:20].[Si:39](Cl)([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].N1C=CN=C1>>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([S:29]([NH:32][CH:33]2[CH2:37][CH2:36][O:35][NH:34]2)(=[O:31])=[O:30])[C:23]=1[O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[S:20] | null | US06680317B2_ | 2,004 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].NC(=S)Nc1ccccc1.[OH:8][c:9]1[c:10]([NH:11][C:12](=[S:13])[NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Br:21])[cH:22][cH:23][c:24]([Cl:25])[c:26]1[S:27](=[O:28])(=[O:29])[NH:30][CH:31]1[CH2:32][CH2:33][O:34][NH:35]1.c1c[nH]cn1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[c:10]([NH:11][C:12](=[S:13])[NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Br:21])[cH:22][cH:23][c:24]([Cl:25])[c:26]1[S:27](=[O:28])(=[O:29])[NH:30][CH:31]1[CH2:32][CH2:33][O:34][NH:35]1 | 0.201798 | CC(C)(C)[Si](C)(C)Cl.NC(=S)Nc1ccccc1.O=S(=O)(NC1CCON1)c1c(Cl)ccc(NC(=S)Nc2ccccc2Br)c1O.c1c[nH]cn1>>CC(C)(C)[Si](C)(C)Oc1c(NC(=S)Nc2ccccc2Br)ccc(Cl)c1S(=O)(=O)NC1CCON1 | CC(C)(C)[Si](C)(C)Cl.NC(=S)Nc1ccccc1.O=S(=O)(NC1CCON1)c1c(Cl)ccc(NC(=S)Nc2ccccc2Br)c1O.c1c[nH]cn1>>CC(C)(C)[Si](C)(C)Oc1c(NC(=S)Nc2ccccc2Br)ccc(Cl)c1S(=O)(=O)NC1CCON1 | US06680317B2_grants | 8001a3bdbd206e42421a29581bb5201cefaa601c5a63e7ac76a064e5 | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].NC(=S)Nc1ccccc1.[OH:8][c:9]1[c:10]([NH:11][C:12](=[S:13])[NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Br:21])[cH:22][cH:23][c:24]([Cl:25])[c:26]1[S:27](=[O:28])(=[O:29])[NH:30][CH:31]1[CH2:32][CH2:33][O:34][NH:35]1.c1c[nH]cn1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[c:10]([NH:11][C:12](=[S:13])[NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Br:21])[cH:22][cH:23][c:24]([Cl:25])[c:26]1[S:27](=[O:28])(=[O:29])[NH:30][CH:31]1[CH2:32][CH2:33][O:34][NH:35]1 | ([C:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:5]-[c:6])>>(Cl-[Si;H0;D4;+0:1](-[C:2])(-[C;D1;H3:3])-[C;D1;H3:4]).([OH;D1;+0:5]-[c:6]) | 78671a61751fb41a7735eaf781f047ef571d6531544684af2f680407 | 1 | 1 | NC(=S)Nc1ccccc1.c1c[nH]cn1 | 746 |
146,697 | 525,792 | 881,259 | C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:13])=[O:12])=[O:4].O.O.[OH-].[Li+].Cl>CO>[CH3:28][O:27][C:25]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[NH:14][S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2])(=[O:12])=[O:13])=[O:26] | |f:2.3.4| | US07491718B2_0406 | 2,009 | CO.C[O:19][C:17]([c:16]1[c:11]([S:8]([NH:7][c:6]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]3[c:22]([cH:21][cH:20]2)[cH:23][cH:24][cH:25][cH:26]3)(=[O:9])=[O:10])[cH:12][cH:13][cH:14][cH:15]1)=[O:18].Cl.O.O.[Li+].[OH-]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12 | 0.473124 | CO.COC(=O)c1ccccc1S(=O)(=O)Nc1ccc2ccccc2c1C(=O)OC.Cl.O.O~[Li+]~[OH-]>>COC(=O)c1c(NS(=O)(=O)c2ccccc2C(=O)O)ccc2ccccc12 | CO.COC(=O)c1ccccc1S(=O)(=O)Nc1ccc2ccccc2c1C(=O)OC.Cl.O.O.[Li+].[OH-]>>COC(=O)c1c(NS(=O)(=O)c2ccccc2C(=O)O)ccc2ccccc12 | US07491718B2_0406grants | 8231b20bd641403f409e25ce615f57f5dc7a69d6bf64decb189b09a7 | CO.C[O:19][C:17]([c:16]1[c:11]([S:8]([NH:7][c:6]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]3[c:22]([cH:21][cH:20]2)[cH:23][cH:24][cH:25][cH:26]3)(=[O:9])=[O:10])[cH:12][cH:13][cH:14][cH:15]1)=[O:18].Cl.O.O.[Li+].[OH-] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12 | ([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.O.O.[Li+].[OH-] | 247 |
80,942 | 326,666 | 554,484 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10] | |f:1.2.3| | US06384080B1_ | 2,002 | CN(C)C=O.I[CH3:1].O=C([O-])[O-].[K+].[K+].[OH:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10] | 0.965207 | CI.CN(C)C=O.Cc1ccc(Cl)c(O)c1.O=C([O-])[O-]~[K+]~[K+]>>COc1cc(C)ccc1Cl | CI.CN(C)C=O.Cc1ccc(Cl)c(O)c1.O=C([O-])[O-].[K+].[K+]>>COc1cc(C)ccc1Cl | US06384080B1_grants | c31f683bd30e788a55cc9f9028be16ad57f72eccfaa61681cdd9de1c | CN(C)C=O.I[CH3:1].O=C([O-])[O-].[K+].[K+].[OH:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[Cl:10] | ([CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3])>>(I-[CH3;D1;+0:1]).([OH;D1;+0:2]-[c:3]) | 473af55be62b6878ca02586dd3897a58e070e2929e5bc4a91d22f6c2 | 1 | 1 | CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 62 |
57,403 | 245,412 | 413,776 | [CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)[CH3:2].O>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH2:10][C:11]2=[O:13])=[CH:7][CH:8]=1)[CH3:2] | |f:2.3| | US05780465_ | 1,998 | CS(=O)(=O)O.O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.O[C:9](=[O:10])[CH2:11][CH2:12][c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:8][cH:7]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12]2 | 0.486066 | CCc1ccc(CCC(=O)O)cc1.CS(=O)(=O)O~O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.O>>CCc1ccc2c(c1)C(=O)CC2 | CCc1ccc(CCC(=O)O)cc1.CS(=O)(=O)O.O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>CCc1ccc2c(c1)C(=O)CC2 | US05780465_grants | c46dd2754d892b966a7227b5e64b6cba757ffc38100f355fa1505334 | CS(=O)(=O)O.O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.O[C:9](=[O:10])[CH2:11][CH2:12][c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:8][cH:7]1 | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:12]2 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3].[c:4]:[cH;D2;+0:5]:[c:6]) | a7d77ace8169e6422b0d679b606a91f7d2decee976f91184f657dc85 | 0 | 1 | CS(=O)(=O)O.O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | 274 |
371,796 | 793,972 | null | Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:9][CH:8]=1.[C:20]([O:24][C:25]([NH:27][C:28]1[C:32]([C:33](O)=[O:34])=[CH:31][N:30]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:29]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[C:36]1([N:30]2[CH:31]=[C:32]([C:33](=[O:34])[NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]3[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([F:16])([F:17])[F:18])=[N:9][CH:8]=3)[C:28]([NH:27][C:25](=[O:26])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[N:29]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1 | |f:0.1,3.4| | US20090286791A1_0808 | 2,009 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.F[P-](F)(F)(F)(F)F.O[C:20]([c:19]1[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:10][n:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1)=[O:21].[NH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[n:38][cH:39]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][n:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]1[C:20](=[O:21])[NH:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[n:38][cH:39]1 | 0.110966 | C1CCOC1.CC(C)(C)OC(=O)Nc1nn(-c2ccccc2)cc1C(=O)O.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.Cl~NCCNC(=O)c1ccc(OCC(F)(F)F)nc1>>CC(C)(C)OC(=O)Nc1nn(-c2ccccc2)cc1C(=O)NCCNC(=O)c1ccc(OCC(F)(F)F)nc1 | C1CCOC1.CC(C)(C)OC(=O)Nc1nn(-c2ccccc2)cc1C(=O)O.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.F[P-](F)(F)(F)(F)F.NCCNC(=O)c1ccc(OCC(F)(F)F)nc1>>CC(C)(C)OC(=O)Nc1nn(-c2ccccc2)cc1C(=O)NCCNC(=O)c1ccc(OCC(F)(F)F)nc1 | US20090286791A1_0808apps | 99ccd90d68c91db7e469f8bbc21c5ff190878c3d04bcac4457926350 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.F[P-](F)(F)(F)(F)F.O[C:20]([c:19]1[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:10][n:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1)=[O:21].[NH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[n:38][cH:39]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][n:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]1[C:20](=[O:21])[NH:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[c:28]1[cH:29][cH:30][c:31]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[n:38][cH:39]1 | ([C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:1).([C:8]-[NH2;D1;+0:9]) | a2d25a527cfbb33347885bb5019f76331a2153345512d2da2f114394 | 1 | 1 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.Cl.F[P-](F)(F)(F)(F)F | 621 |
252,805 | 838,287 | 1,391,850 | [CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]([CH3:17])([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:20][CH2:21][CH2:22][Cl:23].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]([CH3:17])([CH3:16])[C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:20][CH2:21][CH2:22][Cl:23])=[CH:13][CH:14]=1)=[O:8])[CH3:2] | |f:2.3.4| | US08586588B2_1083 | 2,013 | Br[CH2:17][CH2:18][CH2:19][Cl:20].CC#N.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([OH:16])[cH:21][cH:22]1.[K+].[K+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][Cl:20])[cH:21][cH:22]1 | 0.679536 | CC#N.CCOC(=O)CC(C)(C)C(=O)c1ccc(O)cc1.ClCCCBr.O=C([O-])[O-]~[K+]~[K+]>>CCOC(=O)CC(C)(C)C(=O)c1ccc(OCCCCl)cc1 | CC#N.CCOC(=O)CC(C)(C)C(=O)c1ccc(O)cc1.ClCCCBr.O=C([O-])[O-].[K+].[K+]>>CCOC(=O)CC(C)(C)C(=O)c1ccc(OCCCCl)cc1 | US08586588B2_1083grants | 40bf4b65f6ea1676865c16d0265cd9913d1178f64ce6b514314ff235 | Br[CH2:17][CH2:18][CH2:19][Cl:20].CC#N.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([OH:16])[cH:21][cH:22]1.[K+].[K+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][Cl:20])[cH:21][cH:22]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 77cefa6f7285e1367b00e291ad0c233a215688d867a7713380b3385d | 1 | 1 | CC#N.O=C([O-])[O-].[K+].[K+] | 75 |
10,288 | 52,294 | 84,410 | [CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Cl.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH:16]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1 | |f:2.3,4.5| | US04278677_ | 1,981 | Cl.O.O.O=[C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:14][nH:15][c:16]2[cH:17]1.[K+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([C:8]3=[CH:9][CH2:10][NH:11][CH2:12][CH2:13]3)[cH:14][nH:15][c:16]2[cH:17]1 | 0.931704 | COc1ccc2cc[nH]c2c1.Cl.O.O~O=C1CCNCC1.[K+]~[OH-]>>COc1ccc2c(C3=CCNCC3)c[nH]c2c1 | COc1ccc2cc[nH]c2c1.Cl.O.O.O=C1CCNCC1.[K+].[OH-]>>COc1ccc2c(C3=CCNCC3)c[nH]c2c1 | US04278677_grants | 6066ce9997e10b4f29f3a459ecdb45410eeccbedf1556f375269ed88 | Cl.O.O.O=[C:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:14][nH:15][c:16]2[cH:17]1.[K+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([C:8]3=[CH:9][CH2:10][NH:11][CH2:12][CH2:13]3)[cH:14][nH:15][c:16]2[cH:17]1 | ([#7:5]-[C:4]-[CH;D2;+0:3]=[C;H0;D3;+0:1](-[C:2])-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:10]:[c:9]:1)>>(O=[C;H0;D3;+0:1](-[C:2])-[CH2;D2;+0:3]-[C:4]-[#7:5]).([#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1) | d3de57ba81b6c68d5c67f564241e40f0e3c534a84031fd9b85e6e689 | 1 | 1 | Cl.O.O.[K+].[OH-] | 607 |
228,144 | 764,216 | 1,259,450 | [OH-].[K+].[CH3:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[CH:9][CH:10]=2)[C@@H:5]1[NH:14][C:15]1[N:20]=[C:19]([NH2:21])[C:18]([C:22]#[C:23][Si](C)(C)C)=[CH:17][N:16]=1>CO.O>[CH3:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[CH:9][CH:10]=2)[C@@H:5]1[NH:14][C:15]1[N:20]=[C:19]([NH2:21])[C:18]([C:22]#[CH:23])=[CH:17][N:16]=1 | |f:0.1| | US08329717B2_0364 | 2,012 | CO.C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][C@H:8]2[c:9]3[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]3[CH2:16][C@@H:17]2[CH3:18])[n:19][c:20]1[NH2:21].O.[K+].[OH-]>>[CH:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][C@H:8]2[c:9]3[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]3[CH2:16][C@@H:17]2[CH3:18])[n:19][c:20]1[NH2:21] | 0.980984 | CO.Cc1ccc2c(c1)[C@H](Nc1ncc(C#C[Si](C)(C)C)c(N)n1)[C@@H](C)C2.O.[K+]~[OH-]>>C#Cc1cnc(N[C@H]2c3cc(C)ccc3C[C@@H]2C)nc1N | CO.Cc1ccc2c(c1)[C@H](Nc1ncc(C#C[Si](C)(C)C)c(N)n1)[C@@H](C)C2.O.[K+].[OH-]>>C#Cc1cnc(N[C@H]2c3cc(C)ccc3C[C@@H]2C)nc1N | US08329717B2_0364grants | c3805b5213955763471bb27dd0e8b733c7e6eef83cfcc55ec04a7441 | CO.C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][C@H:8]2[c:9]3[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]3[CH2:16][C@@H:17]2[CH3:18])[n:19][c:20]1[NH2:21].O.[K+].[OH-] | [CH:1]#[C:2][c:3]1[cH:4][n:5][c:6]([NH:7][C@H:8]2[c:9]3[cH:10][c:11]([CH3:12])[cH:13][cH:14][c:15]3[CH2:16][C@@H:17]2[CH3:18])[n:19][c:20]1[NH2:21] | ([C:2]#[CH;D1;+0:1])>>(C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]) | 369c1d52dad09f90f7281506a651d2a503963767498d914edaae47e1 | 1 | 1 | CO.O.[K+].[OH-] | 337 |
243,167 | 809,568 | 1,341,292 | NC1C=C(C=CC=1)OC1C=CC(C2N=C(C3CCC3)N3C=CN=C(N)C=23)=CC=1.[CH:29]1([C:33]2[N:37]3[CH:38]=[CH:39][N:40]=[C:41]([NH2:42])[C:36]3=[C:35]([C:43]3[CH:48]=[CH:47][C:46]([O:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[C:45]([N+:56]([O-])=O)[CH:44]=3)[N:34]=2)[CH2:32][CH2:31][CH2:30]1>>[NH2:56][C:45]1[CH:44]=[C:43]([C:35]2[N:34]=[C:33]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[N:37]3[CH:38]=[CH:39][N:40]=[C:41]([NH2:42])[C:36]=23)[CH:48]=[CH:47][C:46]=1[O:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1 | null | US08481733B2_0496 | 2,013 | Nc1cccc(Oc2ccc(-c3nc(C4CCC4)n4ccnc(N)c34)cc2)c1.O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11]3)[n:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[c:18]23)[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11]3)[n:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[c:18]23)[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1 | 0.606666 | Nc1cccc(Oc2ccc(-c3nc(C4CCC4)n4ccnc(N)c34)cc2)c1.Nc1nccn2c(C3CCC3)nc(-c3ccc(Oc4ccccc4)c([N+](=O)[O-])c3)c12>>Nc1cc(-c2nc(C3CCC3)n3ccnc(N)c23)ccc1Oc1ccccc1 | Nc1cccc(Oc2ccc(-c3nc(C4CCC4)n4ccnc(N)c34)cc2)c1.Nc1nccn2c(C3CCC3)nc(-c3ccc(Oc4ccccc4)c([N+](=O)[O-])c3)c12>>Nc1cc(-c2nc(C3CCC3)n3ccnc(N)c23)ccc1Oc1ccccc1 | US08481733B2_0496grants | ff77115d40d9ce1e9b88279fcdcbdd5baa79ad21f315346e1bba9177 | Nc1cccc(Oc2ccc(-c3nc(C4CCC4)n4ccnc(N)c34)cc2)c1.O=[N+:1]([O-])[c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11]3)[n:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[c:18]23)[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1 | [NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][c:7]([CH:8]3[CH2:9][CH2:10][CH2:11]3)[n:12]3[cH:13][cH:14][n:15][c:16]([NH2:17])[c:18]23)[cH:19][cH:20][c:21]1[O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 0.5 | 2 | Nc1cccc(Oc2ccc(-c3nc(C4CCC4)n4ccnc(N)c34)cc2)c1 | 1 |
425,175 | 1,804,947 | null | [Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]1[NH:20][C:21]1[N:22]=[CH:23][C:24]2[CH2:30][NH:29][CH2:28][CH2:27][C:25]=2[N:26]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([N:29]2[CH2:28][CH2:27][C:25]3[N:26]=[C:21]([NH:20][CH:12]4[CH2:11][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[CH2:13]4)[N:22]=[CH:23][C:24]=3[CH2:30]2)=[O:10])=[CH:4][CH:3]=1 | |f:2.3| | US20150368240A1_0111 | 2,015 | CCN=C=NCCCN(C)C.Cl.ClCCl.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1.[NH:10]1[CH2:11][CH2:12][c:13]2[n:14][c:15]([NH:16][CH:17]3[CH2:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[CH2:25]3)[n:26][cH:27][c:28]2[CH2:29]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1)[N:10]1[CH2:11][CH2:12][c:13]2[n:14][c:15]([NH:16][CH:17]3[CH2:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[CH2:25]3)[n:26][cH:27][c:28]2[CH2:29]1 | 0.719285 | CCN=C=NCCCN(C)C~Cl.ClCCl.O=C(O)c1ccc(Cl)nn1.c1ccc2c(c1)CC(Nc1ncc3c(n1)CCNC3)C2>>O=C(c1ccc(Cl)nn1)N1CCc2nc(NC3Cc4ccccc4C3)ncc2C1 | CCN=C=NCCCN(C)C.Cl.ClCCl.O=C(O)c1ccc(Cl)nn1.c1ccc2c(c1)CC(Nc1ncc3c(n1)CCNC3)C2>>O=C(c1ccc(Cl)nn1)N1CCc2nc(NC3Cc4ccccc4C3)ncc2C1 | US20150368240A1_0111apps | 5cf4c2501aa5e130e3dff91941145c445a6f719b794d5301ab5ed0e2 | CCN=C=NCCCN(C)C.Cl.ClCCl.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1.[NH:10]1[CH2:11][CH2:12][c:13]2[n:14][c:15]([NH:16][CH:17]3[CH2:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[CH2:25]3)[n:26][cH:27][c:28]2[CH2:29]1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][n:9]1)[N:10]1[CH2:11][CH2:12][c:13]2[n:14][c:15]([NH:16][CH:17]3[CH2:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[CH2:25]3)[n:26][cH:27][c:28]2[CH2:29]1 | ([#7;a:5]:[#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6])-[C:8])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]:[#7;a:5]).([C:6]-[NH;D2;+0:7]-[C:8]) | 3b2f6aec0a5b15474e8d3e5e54c77d4c7a6db409c225cfbbb1c66d17 | 1 | 1 | CCN=C=NCCCN(C)C.Cl.ClCCl | 663 |
284,963 | 931,129 | 1,560,136 | [CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9](Br)=[CH:8]2)=[O:4].[CH3:25][O:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.Cl>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[CH:32]=1)=[CH:8]2)=[O:4] | |f:2.3.4.5,9.10.11,12.13.14| | US08921389B2_0858 | 2,014 | Br[c:11]1[cH:10][c:9]2[c:8]([cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:30]2[OH:31])[n:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:20]1=[O:21].CC(=O)[O-].CC(=O)[O-].CCOC(C)=O.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.Cl.O.O.O=P([O-])([O-])[O-].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]1.[Cl-].[K+].[K+].[K+].[Na+].[Pd+2]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]2[c:9]([cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]3)[c:20](=[O:21])[n:22]2[CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]1[OH:31] | 0.731266 | CC(=O)[O-]~CC(=O)[O-]~[Pd+2].CCOC(C)=O.COC(=O)c1ncc2c(cc(Br)c(=O)n2Cc2ccccc2)c1O.COc1cccc(B(O)O)c1.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.Cl.O.O=P([O-])([O-])[O-]~[K+]~[K+]~[K+].O~[Cl-]~[Na+]>>COC(=O)c1ncc2c(cc(-c3cccc(OC)c3)c(=O)n2Cc2ccccc2)c1O | CC(=O)[O-].CC(=O)[O-].CCOC(C)=O.COC(=O)c1ncc2c(cc(Br)c(=O)n2Cc2ccccc2)c1O.COc1cccc(B(O)O)c1.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.Cl.O.O.O=P([O-])([O-])[O-].[Cl-].[K+].[K+].[K+].[Na+].[Pd+2]>>COC(=O)c1ncc2c(cc(-c3cccc(OC)c3)c(=O)n2Cc2ccccc2)c1O | US08921389B2_0858grants | bc4e23bd8fbe6c930d7e1d17e3c7b3acd46c784dc8edc82fbaef3096 | Br[c:11]1[cH:10][c:9]2[c:8]([cH:7][n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:30]2[OH:31])[n:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:20]1=[O:21].CC(=O)[O-].CC(=O)[O-].CCOC(C)=O.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.Cl.O.O.O=P([O-])([O-])[O-].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]1.[Cl-].[K+].[K+].[K+].[Na+].[Pd+2] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][cH:7][c:8]2[c:9]([cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19]3)[c:20](=[O:21])[n:22]2[CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[c:30]1[OH:31] | ([#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-].CCOC(C)=O.COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.Cl.O.O.O=P([O-])([O-])[O-].[Cl-].[K+].[K+].[K+].[Na+].[Pd+2] | 833 |
382,809 | 977,959 | null | Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([N:15]([CH3:17])[CH3:16])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([NH:29][C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N:15]([CH3:17])[CH3:16])[CH:10]=3)=[CH:6][N:7]=2)[CH:30]=[CH:31][CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1 | |f:3.4.5| | US20100298325A1_0336 | 2,010 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCOC(C)=O.Cl[c:13]1[cH:12][cH:11][c:10]([O:9][c:8]2[cH:7][cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:31]2)[cH:30][n:29]1.O=C([O-])[O-].[Cs+].[Cs+].[NH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[n:29][cH:30]2)[cH:31]1 | 0.840335 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCOC(C)=O.CN(C)c1cccc(Oc2ccc(Cl)nc2)c1.Nc1cccc(OCc2ccccc2)c1.O=C([O-])[O-]~[Cs+]~[Cs+]>>CN(C)c1cccc(Oc2ccc(Nc3cccc(OCc4ccccc4)c3)nc2)c1 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCOC(C)=O.CN(C)c1cccc(Oc2ccc(Cl)nc2)c1.Nc1cccc(OCc2ccccc2)c1.O=C([O-])[O-].[Cs+].[Cs+]>>CN(C)c1cccc(Oc2ccc(Nc3cccc(OCc4ccccc4)c3)nc2)c1 | US20100298325A1_0336apps | 108737d6bc35ba69e520d61c778c95edcb6ee5f0057fb7ca62e45b84 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCOC(C)=O.Cl[c:13]1[cH:12][cH:11][c:10]([O:9][c:8]2[cH:7][cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:31]2)[cH:30][n:29]1.O=C([O-])[O-].[Cs+].[Cs+].[NH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1 | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[n:29][cH:30]2)[cH:31]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([NH2;D1;+0:4]-[c:5]) | d3c0e3d30997502d61c408a05ad1cdc8f5709f145f8cf173e0a3ac8a | 1 | 1 | C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.CCOC(C)=O.O=C([O-])[O-].[Cs+].[Cs+] | 434 |
190,436 | 655,721 | 1,083,512 | [CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.C([O-])(=O)C.[Na+].[Br:16]Br.O>C(O)(=O)C>[Br:16][C:10]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8] | |f:1.2| | US07960365B2_0089 | 2,011 | Br[Br:11].CC(=O)O.CC(=O)[O-].O.[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[cH:9][cH:10]1.[Na+]>>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[cH:9][c:10]1[Br:11] | 0.505204 | BrBr.CC(=O)O.CC(=O)[O-]~[Na+].COc1ccc(C#N)cn1.O>>COc1ncc(C#N)cc1Br | BrBr.CC(=O)O.CC(=O)[O-].COc1ccc(C#N)cn1.O.[Na+]>>COc1ncc(C#N)cc1Br | US07960365B2_0089grants | b187fd8253057d428806ace2a91eca235928e0a025ae2287a800683b | Br[Br:11].CC(=O)O.CC(=O)[O-].O.[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[cH:9][cH:10]1.[Na+] | [CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[cH:9][c:10]1[Br:11] | ([#7;a:2]:[c:3]:[c;H0;D3;+0:4](-[Br;H0;D1;+0:1]):[c:5])>>(Br-[Br;H0;D1;+0:1]).([#7;a:2]:[c:3]:[cH;D2;+0:4]:[c:5]) | 8015940f0b9f5a68b5745eca48e4c46f402b06ba03cf89c253988a76 | 1 | 1 | CC(=O)O.CC(=O)[O-].O.[Na+] | 292 |
192,814 | 663,331 | 1,097,649 | C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=1.[NH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>C1COCC1.O.C(=O)(O)[O-].[Na+]>[OH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:28])=[CH:29][CH:30]=1 | |f:6.7| | US07989457B2_0218 | 2,011 | C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O.O=C([O-])O.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH2:8].[Na+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1 | 0.807613 | C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(=O)CCN.O.O=C(O)c1ccc(O)cc1.O=C([O-])O~[Na+]>>CCOC(=O)CCNC(=O)c1ccc(O)cc1 | C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(=O)CCN.O.O=C(O)c1ccc(O)cc1.O=C([O-])O.[Na+]>>CCOC(=O)CCNC(=O)c1ccc(O)cc1 | US07989457B2_0218grants | 2318b274ef46ccc65ea71c4ef4669611a58009727ca925f8d9aa61c2 | C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O.O=C([O-])O.O[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH2:8].[Na+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]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 | C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.O.O=C([O-])O.[Na+] | 334 |
61,937 | 261,356 | 442,294 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:23][CH3:24])[C:11]=1[O:12][CH2:13]/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16])[C:6]([OH:8])=O.[NH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:32][CH3:33]>>[CH2:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][NH:25][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([O:23][CH3:24])[C:11]([O:12][CH2:13]/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:33] | null | US05925667_ | 1,999 | O[C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH2:19]/[CH:20]=[C:21](\[CH3:22])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[c:29]([O:30][CH3:31])[cH:32]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][NH2:9]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH2:19]/[CH:20]=[C:21](\[CH3:22])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[c:29]([O:30][CH3:31])[cH:32]1 | 0.504367 | CCN1CCCC1CN.COc1cc(C(=O)O)cc(OC)c1OC/C=C(\C)CCC=C(C)C>>CCN1CCCC1CNC(=O)c1cc(OC)c(OC/C=C(\C)CCC=C(C)C)c(OC)c1 | CCN1CCCC1CN.COc1cc(C(=O)O)cc(OC)c1OC/C=C(\C)CCC=C(C)C>>CCN1CCCC1CNC(=O)c1cc(OC)c(OC/C=C(\C)CCC=C(C)C)c(OC)c1 | US05925667_grants | 528f870dd0511a18d8c21f1d2cb7d94e449c841692c352119358d28c | O[C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH2:19]/[CH:20]=[C:21](\[CH3:22])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[c:29]([O:30][CH3:31])[cH:32]1.[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][NH2:9] | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH2:19]/[CH:20]=[C:21](\[CH3:22])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[c:29]([O:30][CH3:31])[cH:32]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 | null | 334 |
331,752 | 125,287 | null | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19](=[O:31])[NH:20][C:21](=[O:30])[C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:13][CH:12]=1)(O)=[O:7].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19](=[O:31])[NH:20][C:21](=[O:30])[C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:13][CH:12]=1)=[O:7] | |f:2.3| | US20040010031A1_0598 | 2,004 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.Cl.O[C:6](=[O:7])[CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([NH:14][C:15]2=[C:16]([c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1.On1nnc2ccccc21.[CH3:1][O:2][CH2:3][CH2:4][NH2:5]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([NH:14][C:15]2=[C:16]([c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1 | 0.793698 | C1CCOC1.CCN=C=NCCCN(C)C~Cl.CCOC(C)=O.COCCN.O=C(O)CSc1ccc(NC2=C(c3ccc(Cl)cc3)C(=O)NC2=O)cc1.On1nnc2ccccc21>>COCCNC(=O)CSc1ccc(NC2=C(c3ccc(Cl)cc3)C(=O)NC2=O)cc1 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.COCCN.Cl.O=C(O)CSc1ccc(NC2=C(c3ccc(Cl)cc3)C(=O)NC2=O)cc1.On1nnc2ccccc21>>COCCNC(=O)CSc1ccc(NC2=C(c3ccc(Cl)cc3)C(=O)NC2=O)cc1 | US20040010031A1_0598apps | 769aad5b806db33d421c97c33735881e04acf18042a7ef38684e1682 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.Cl.O[C:6](=[O:7])[CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([NH:14][C:15]2=[C:16]([c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1.On1nnc2ccccc21.[CH3:1][O:2][CH2:3][CH2:4][NH2:5] | [CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([NH:14][C:15]2=[C:16]([c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[C:24](=[O:25])[NH:26][C:27]2=[O:28])[cH:29][cH:30]1 | ([C: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]).([C:4]-[NH2;D1;+0:5]) | 9700dfbbea18932b10f40ed49527a6efd0b261364d0b5e3b1e240441 | 0.333333 | 3 | C1CCOC1.CCN=C=NCCCN(C)C.CCOC(C)=O.Cl.On1nnc2ccccc21 | 230 |
85,812 | 343,182 | 586,013 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[NH:27]([CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH:18]=2)[CH2:25][CH2:24]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1 | null | US06498169B1_ | 2,002 | O=[C:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[cH:7][c:6](-[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[c:27]([O:28][CH3:29])[cH:26]3)[n:25][cH:24][cH:23]2)[CH2:22][CH2:21]1.[NH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]3[CH2:11][CH2:12][CH:13]([NH:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[CH2:21][CH2:22]3)[cH:23][cH:24][n:25]2)[cH:26][c:27]([O:28][CH3:29])[c:30]1[O:31][CH3:32] | 0.884502 | COc1cc(-c2cc(CN3CCC(=O)CC3)ccn2)cc(OC)c1OC.Nc1ccccc1>>COc1cc(-c2cc(CN3CCC(Nc4ccccc4)CC3)ccn2)cc(OC)c1OC | COc1cc(-c2cc(CN3CCC(=O)CC3)ccn2)cc(OC)c1OC.Nc1ccccc1>>COc1cc(-c2cc(CN3CCC(Nc4ccccc4)CC3)ccn2)cc(OC)c1OC | US06498169B1_grants | aed017dbf679901a8954d183b64970a9572293a2d55fc4b40a61b52f | O=[C:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[cH:7][c:6](-[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[c:27]([O:28][CH3:29])[cH:26]3)[n:25][cH:24][cH:23]2)[CH2:22][CH2:21]1.[NH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]3[CH2:11][CH2:12][CH:13]([NH:14][c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[CH2:21][CH2:22]3)[cH:23][cH:24][n:25]2)[cH:26][c:27]([O:28][CH3:29])[c:30]1[O:31][CH3:32] | ([C:2]-[CH;D3;+0:1](-[C:3])-[NH;D2;+0:4]-[c:5])>>(O=[C;H0;D3;+0:1](-[C:2])-[C:3]).([NH2;D1;+0:4]-[c:5]) | 23da8654ddd3ed97bf79549827e10625994127937e9617a0b767cf82 | 1 | 1 | null | 469 |
281,947 | 923,649 | 1,545,890 | [Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C:14]([F:13])([F:25])[F:26])[CH:17]=2)[N:3]=1 | |f:2.3.4| | US08901145B2_0489 | 2,014 | C1CCOC1.Cl[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:22][c:20]([Cl:21])[n:19]1.O=C([O-])[O-].OB(O)[c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18]1.[Na+].[Na+]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18]2)[n:19][c:20]([Cl:21])[n:22]1 | 0.279754 | C1CCOC1.COC(=O)c1cc(Cl)nc(Cl)n1.O=C([O-])[O-]~[Na+]~[Na+].OB(O)c1cccc(OC(F)(F)F)c1>>COC(=O)c1cc(-c2cccc(OC(F)(F)F)c2)nc(Cl)n1 | C1CCOC1.COC(=O)c1cc(Cl)nc(Cl)n1.O=C([O-])[O-].OB(O)c1cccc(OC(F)(F)F)c1.[Na+].[Na+]>>COC(=O)c1cc(-c2cccc(OC(F)(F)F)c2)nc(Cl)n1 | US08901145B2_0489grants | c072e4ffd90737b2bd47536f27aaa8076b62daa897ca6167a50f30f5 | C1CCOC1.Cl[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:22][c:20]([Cl:21])[n:19]1.O=C([O-])[O-].OB(O)[c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18]1.[Na+].[Na+] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][C:14]([F:15])([F:16])[F:17])[cH:18]2)[n:19][c:20]([Cl:21])[n:22]1 | ([c:8]:[c;H0;D3;+0:7](:[c:9])-[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).(O-B(-O)-[c;H0;D3;+0:7](:[c:8]):[c:9]) | c7c66d480f7dc9471f82622ca551cc7173650fb4e8aaaa72d95d4746 | 1 | 1 | C1CCOC1.O=C([O-])[O-].[Na+].[Na+] | 884 |
50,839 | 220,391 | 361,870 | [H-].[Na+].C1(S)C=CC=CC=1.C[O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[N:24]1[CH2:29][CH2:28][CH:27]([N:30]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([CH3:41])[CH:37]=3)[N:32]([CH3:42])[C:31]2=[O:43])[CH2:26][CH2:25]1.O>CN(C=O)C>[OH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][N:16]=[C:15]2[N:24]1[CH2:29][CH2:28][CH:27]([N:30]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([CH3:41])[CH:37]=3)[N:32]([CH3:42])[C:31]2=[O:43])[CH2:26][CH2:25]1 | |f:0.1| | US05605900_ | 1,997 | CN(C)C=O.C[O:33][c:32]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([n:14]4[c:15](=[O:16])[c:17]5[cH:18][c:19]([CH3:20])[cH:21][cH:22][c:23]5[n:24]([CH3:25])[c:26]4=[O:27])[CH2:28][CH2:29]3)[c:30]2[cH:31]1.O.Sc1ccccc1.[H-].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([n:14]4[c:15](=[O:16])[c:17]5[cH:18][c:19]([CH3:20])[cH:21][cH:22][c:23]5[n:24]([CH3:25])[c:26]4=[O:27])[CH2:28][CH2:29]3)[c:30]2[cH:31][c:32]1[OH:33] | 0.891912 | CN(C)C=O.COc1cc2ncnc(N3CCC(n4c(=O)c5cc(C)ccc5n(C)c4=O)CC3)c2cc1OC.O.Sc1ccccc1.[H-]~[Na+]>>COc1cc2ncnc(N3CCC(n4c(=O)c5cc(C)ccc5n(C)c4=O)CC3)c2cc1O | CN(C)C=O.COc1cc2ncnc(N3CCC(n4c(=O)c5cc(C)ccc5n(C)c4=O)CC3)c2cc1OC.O.Sc1ccccc1.[H-].[Na+]>>COc1cc2ncnc(N3CCC(n4c(=O)c5cc(C)ccc5n(C)c4=O)CC3)c2cc1O | US05605900_grants | 5553ffdd218d71a7eb3da219e2eca6691a0d96fb38cf04336fb5872a | CN(C)C=O.C[O:33][c:32]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([n:14]4[c:15](=[O:16])[c:17]5[cH:18][c:19]([CH3:20])[cH:21][cH:22][c:23]5[n:24]([CH3:25])[c:26]4=[O:27])[CH2:28][CH2:29]3)[c:30]2[cH:31]1.O.Sc1ccccc1.[H-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][CH:13]([n:14]4[c:15](=[O:16])[c:17]5[cH:18][c:19]([CH3:20])[cH:21][cH:22][c:23]5[n:24]([CH3:25])[c:26]4=[O:27])[CH2:28][CH2:29]3)[c:30]2[cH:31][c:32]1[OH:33] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | CN(C)C=O.O.Sc1ccccc1.[H-].[Na+] | 48 |
125,798 | 463,456 | 784,920 | [C:1](O)(=O)CCC(O)=O.[F:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:17]=3[C:16]([N:28]3[CH2:33][CH2:32][NH:31][CH:30]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=4)[CH2:29]3)=[N:15][C:14]=2[CH:44]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCl.[Cl-].[Na+]>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:17]=3[C:16]([N:28]3[CH2:33][CH2:32][N:31]([CH3:1])[CH:30]([CH2:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=4)[CH2:29]3)=[N:15][C:14]=2[CH:44]=1 | |f:0.1,2.3,6.7| | US07214673B2_0825 | 2,007 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O=C(O)CCC(=O)O.O=[CH2:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]2[CH2:10][N:11]([C:12]3=[N:13][c:14]4[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]4[NH:21][c:22]4[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]43)[CH2:32][CH2:33][NH:34]2)[cH:36][cH:37]1.[Cl-].[Na+].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]2[CH2:10][N:11]([C:12]3=[N:13][c:14]4[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]4[NH:21][c:22]4[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]43)[CH2:32][CH2:33][N:34]2[CH3:35])[cH:36][cH:37]1 | 0.203405 | C=O.CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].COc1ccc(CCC2CN(C3=Nc4cc(F)ccc4Nc4ccc(C(F)(F)F)cc43)CCN2)cc1~O=C(O)CCC(=O)O.ClCCl.[Cl-]~[Na+]>>COc1ccc(CCC2CN(C3=Nc4cc(F)ccc4Nc4ccc(C(F)(F)F)cc43)CCN2C)cc1 | C=O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.COc1ccc(CCC2CN(C3=Nc4cc(F)ccc4Nc4ccc(C(F)(F)F)cc43)CCN2)cc1.ClCCl.O=C(O)CCC(=O)O.[Cl-].[Na+].[Na+]>>COc1ccc(CCC2CN(C3=Nc4cc(F)ccc4Nc4ccc(C(F)(F)F)cc43)CCN2C)cc1 | US07214673B2_0825grants | 4ac879182e8c82a18e232ba4f7099b5b1a22bc9078bf4d02b4ead9f2 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O=C(O)CCC(=O)O.O=[CH2:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]2[CH2:10][N:11]([C:12]3=[N:13][c:14]4[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]4[NH:21][c:22]4[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]43)[CH2:32][CH2:33][NH:34]2)[cH:36][cH:37]1.[Cl-].[Na+].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH:9]2[CH2:10][N:11]([C:12]3=[N:13][c:14]4[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]4[NH:21][c:22]4[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]43)[CH2:32][CH2:33][N:34]2[CH3:35])[cH:36][cH:37]1 | ([C:2]-[N;H0;D3;+0:3](-[C:4])-[CH3;D1;+0:1])>>(O=[CH2;D1;+0:1]).([C:2]-[NH;D2;+0:3]-[C:4]) | fb44fedb5e2cc8d07bdd0b6fb6f327584934b65e8fb8e97e63bb7532 | 1 | 1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O=C(O)CCC(=O)O.[Cl-].[Na+].[Na+] | 217 |
338,140 | 259,598 | null | [Si:1]([O:8][CH:9]([CH2:15][C:16]#[CH:17])[C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Si:1]([O:8][CH:9]([CH2:15][C:16]#[CH:17])[C:10]([CH3:14])([CH3:13])[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2] | |f:1.2.3| | US20050131242A1_0068 | 2,005 | ClCCl.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].[CH:1]#[C:2][CH2:3][CH:4]([O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([CH3:14])([CH3:15])[CH2:16][OH:17].c1cc[nH+]cc1.c1cc[nH+]cc1>>[CH:1]#[C:2][CH2:3][CH:4]([O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([CH3:14])([CH3:15])[CH:16]=[O:17] | 0.28356 | C#CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)CO.ClCCl.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-]~c1cc[nH+]cc1~c1cc[nH+]cc1>>C#CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C=O | C#CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)CO.ClCCl.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].c1cc[nH+]cc1.c1cc[nH+]cc1>>C#CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C=O | US20050131242A1_0068apps | 20af783679a0737eac343ab8cc7eda4ece30656cbf7105b8ce8d93f1 | ClCCl.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].[CH:1]#[C:2][CH2:3][CH:4]([O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([CH3:14])([CH3:15])[CH2:16][OH:17].c1cc[nH+]cc1.c1cc[nH+]cc1 | [CH:1]#[C:2][CH2:3][CH:4]([O:5][Si:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([CH3:14])([CH3:15])[CH:16]=[O:17] | ([C:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3])>>([C:1]-[CH2;D2;+0:2]-[OH;D1;+0:3]) | 61df3886a0291f08a9e9f8293588d04d916daa376a54f86534b439c2 | 1 | 1 | ClCCl.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].c1cc[nH+]cc1.c1cc[nH+]cc1 | 142 |
217,097 | 730,521 | 1,203,528 | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:21])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:21])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])=[O:5])[CH3:2] | null | US08202858B2_0184 | 2,012 | CO.O=[N+:19]([O-])[c:18]1[c:13]([NH:12][c:11]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][n:9]2[CH3:10])[cH:14][cH:15][cH:16][cH:17]1.[Pd]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][n:9]([CH3:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[NH2:19] | 0.972063 | CCOC(=O)c1cnn(C)c1Nc1ccccc1[N+](=O)[O-].CO.[Pd]>>CCOC(=O)c1cnn(C)c1Nc1ccccc1N | CCOC(=O)c1cnn(C)c1Nc1ccccc1[N+](=O)[O-].CO.[Pd]>>CCOC(=O)c1cnn(C)c1Nc1ccccc1N | US08202858B2_0184grants | 3ca509f56145d4570e37113694703726c8cb8fcf5b8e5bd7332e32dd | CO.O=[N+:19]([O-])[c:18]1[c:13]([NH:12][c:11]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][n:9]2[CH3:10])[cH:14][cH:15][cH:16][cH:17]1.[Pd] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][n:9]([CH3:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[NH2:19] | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
444,078 | 1,933,184 | null | [NH:1]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:2]1.C([O-])(O)=O.[Na+].[CH3:20][C:21]([O:24][C:25](O[C:25]([O:24][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:26])=[O:26])([CH3:23])[CH3:22]>C1COCC1>[N:1]1([C:25]([O:24][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:26])[CH2:2][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:6]1 | |f:1.2| | US20160264552A1_0558 | 2,016 | C1CCOC1.CC(C)(C)OC(=O)O[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].O=C([O-])O.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([C:8](=[O:9])[O:10][CH3:11])[CH2:12][NH:13][CH2:21]1.[Na+]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([C:8](=[O:9])[O:10][CH3:11])[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1 | 0.265621 | C1CCOC1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.COC(=O)C1CNCC(C(=O)OC)C1.O=C([O-])O~[Na+]>>COC(=O)C1CC(C(=O)OC)CN(C(=O)OC(C)(C)C)C1 | C1CCOC1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.COC(=O)C1CNCC(C(=O)OC)C1.O=C([O-])O.[Na+]>>COC(=O)C1CC(C(=O)OC)CN(C(=O)OC(C)(C)C)C1 | US20160264552A1_0558apps | 58408563a15493081d6c75146d7821b97dda78a5622f5a2ef6bbad6c | C1CCOC1.CC(C)(C)OC(=O)O[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].O=C([O-])O.[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([C:8](=[O:9])[O:10][CH3:11])[CH2:12][NH:13][CH2:21]1.[Na+] | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([C:8](=[O:9])[O:10][CH3:11])[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1 | ([C:8]-[N;H0;D3;+0:9](-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])>>(C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]).([C:8]-[NH;D2;+0:9]-[C:10]) | 4adaee2f919129a728a81156383c0a0b04988e7bc84e82c9b95523a9 | 1 | 1 | C1CCOC1.O=C([O-])O.[Na+] | 694 |
184,414 | 638,608 | 1,055,763 | [NH2:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])=[CH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH:19]1([S:22](Cl)(=[O:24])=[O:23])[CH2:21][CH2:20]1.Cl>N1C=CC=CC=1>[F:18][C:12]1[CH:13]=[C:14]([I:17])[CH:15]=[CH:16][C:11]=1[NH:10][C:3]1[C:2]([NH:1][S:22]([CH:19]2[CH2:21][CH2:20]2)(=[O:24])=[O:23])=[CH:7][N:6]([CH3:8])[C:5](=[O:9])[CH:4]=1 | null | US07897624B2_0475 | 2,011 | Cl.Cl[S:6](=[O:7])(=[O:8])[CH:9]1[CH2:10][CH2:11]1.[CH3:1][n:2]1[cH:3][c:4]([NH2:5])[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([I:18])[cH:19][c:20]2[F:21])[cH:22][c:23]1=[O:24].c1ccncc1>>[CH3:1][n:2]1[cH:3][c:4]([NH:5][S:6](=[O:7])(=[O:8])[CH:9]2[CH2:10][CH2:11]2)[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([I:18])[cH:19][c:20]2[F:21])[cH:22][c:23]1=[O:24] | 0.64868 | Cl.Cn1cc(N)c(Nc2ccc(I)cc2F)cc1=O.O=S(=O)(Cl)C1CC1.c1ccncc1>>Cn1cc(NS(=O)(=O)C2CC2)c(Nc2ccc(I)cc2F)cc1=O | Cl.Cn1cc(N)c(Nc2ccc(I)cc2F)cc1=O.O=S(=O)(Cl)C1CC1.c1ccncc1>>Cn1cc(NS(=O)(=O)C2CC2)c(Nc2ccc(I)cc2F)cc1=O | US07897624B2_0475grants | 21ecab958b2376e3c7b29417542f855309d4ee41c484dec9ea900956 | Cl.Cl[S:6](=[O:7])(=[O:8])[CH:9]1[CH2:10][CH2:11]1.[CH3:1][n:2]1[cH:3][c:4]([NH2:5])[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([I:18])[cH:19][c:20]2[F:21])[cH:22][c:23]1=[O:24].c1ccncc1 | [CH3:1][n:2]1[cH:3][c:4]([NH:5][S:6](=[O:7])(=[O:8])[CH:9]2[CH2:10][CH2:11]2)[c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([I:18])[cH:19][c:20]2[F:21])[cH:22][c:23]1=[O:24] | ([#7;a:5]:[c:6]:[c:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](-[C:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([#7;a:5]:[c:6]:[c:7]-[NH2;D1;+0:8]) | 3bf888044cd77f614c714cddf13915556a9febb0ceeb35a813621a8b | 1 | 1 | Cl.c1ccncc1 | 812 |
48,255 | 210,729 | 340,599 | [CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[C:30]([O:35][CH3:36])=[CH:31][CH:32]=[C:33]([CH3:34])[C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:18]([C:23]([OH:25])=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)[C:8]2[C:30]([O:35][CH3:36])=[CH:31][CH:32]=[C:33]([CH3:34])[C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4] | null | US05541229_ | 1,996 | CC(C)(C)[O:30][C:28]([c:27]1[c:22](-[c:21]2[cH:20][cH:19][c:18]([CH2:17][n:16]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[c:8]([CH3:9])[cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]43)[cH:32][cH:31]2)[cH:23][cH:24][cH:25][cH:26]1)=[O:29].ClCCl.O=C(O)C(F)(F)F>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]2[n:16]1[CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28](=[O:29])[OH:30])[cH:31][cH:32]1 | 0.941362 | CCCCc1nc2c(C)ccc(OC)c2n1Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1.ClCCl.O=C(O)C(F)(F)F>>CCCCc1nc2c(C)ccc(OC)c2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | CCCCc1nc2c(C)ccc(OC)c2n1Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1.ClCCl.O=C(O)C(F)(F)F>>CCCCc1nc2c(C)ccc(OC)c2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | US05541229_grants | 85559d563d50dc2d9e976d97e7a15aaef5d466da1fc25b1e8a9082e1 | CC(C)(C)[O:30][C:28]([c:27]1[c:22](-[c:21]2[cH:20][cH:19][c:18]([CH2:17][n:16]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[c:8]([CH3:9])[cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]43)[cH:32][cH:31]2)[cH:23][cH:24][cH:25][cH:26]1)=[O:29].ClCCl.O=C(O)C(F)(F)F | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([CH3:9])[cH:10][cH:11][c:12]([O:13][CH3:14])[c:15]2[n:16]1[CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[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-C(-C)(-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) | 19099d615ac8e69cee786c921f9ac0f1b45fdfafec5366cce7c8840f | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 752 |
187,260 | 646,841 | 1,070,223 | [Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[N:13]([CH3:33])[C:14]([C:16]1[S:32][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([C:29]([OH:31])=O)=[CH:25][C:21]=3[O:22][CH2:23][CH2:24][C:18]=2[CH:17]=1)=[O:15].[NH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:40])[CH3:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[C:38]([NH:37][CH2:36][CH2:35][NH:34][C:29]([C:26]1[CH:27]=[CH:28][C:20]2[C:19]3[S:32][C:16]([C:14]([N:13]([C:3]4[CH:4]=[CH:5][C:6]([C:8](=[O:12])[N:9]([CH3:10])[CH3:11])=[CH:7][C:2]=4[Cl:1])[CH3:33])=[O:15])=[CH:17][C:18]=3[CH2:24][CH2:23][O:22][C:21]=2[CH:25]=1)=[O:31])(=[O:40])[CH3:39] | |f:2.3| | US07928248B2_0726 | 2,011 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][c:19]1[cH:20][c:21]([C:22](=[O:23])[N:24]([CH3:25])[c:26]3[cH:27][cH:28][c:29]([C:30](=[O:31])[N:32]([CH3:33])[CH3:34])[cH:35][c:36]3[Cl:37])[s:38][c:39]1-2.[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH2:7]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][c:19]1[cH:20][c:21]([C:22](=[O:23])[N:24]([CH3:25])[c:26]3[cH:27][cH:28][c:29]([C:30](=[O:31])[N:32]([CH3:33])[CH3:34])[cH:35][c:36]3[Cl:37])[s:38][c:39]1-2 | 0.664499 | C1CCOC1.CC(=O)NCCN.CCN(C(C)C)C(C)C.CN(C)C(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C(=O)O)cc2OCC3)c(Cl)c1.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F>>CC(=O)NCCNC(=O)c1ccc2c(c1)OCCc1cc(C(=O)N(C)c3ccc(C(=O)N(C)C)cc3Cl)sc1-2 | C1CCOC1.CC(=O)NCCN.CCN(C(C)C)C(C)C.CN(C)C(=O)c1ccc(N(C)C(=O)c2cc3c(s2)-c2ccc(C(=O)O)cc2OCC3)c(Cl)c1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F>>CC(=O)NCCNC(=O)c1ccc2c(c1)OCCc1cc(C(=O)N(C)c3ccc(C(=O)N(C)C)cc3Cl)sc1-2 | US07928248B2_0726grants | cda0feaf899eb98cd536a92e121c1334895d2b20c7b10b498726f9c8 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F.O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][c:19]1[cH:20][c:21]([C:22](=[O:23])[N:24]([CH3:25])[c:26]3[cH:27][cH:28][c:29]([C:30](=[O:31])[N:32]([CH3:33])[CH3:34])[cH:35][c:36]3[Cl:37])[s:38][c:39]1-2.[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH2:7] | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][c:19]1[cH:20][c:21]([C:22](=[O:23])[N:24]([CH3:25])[c:26]3[cH:27][cH:28][c:29]([C:30](=[O:31])[N:32]([CH3:33])[CH3:34])[cH:35][c:36]3[Cl:37])[s:38][c:39]1-2 | ([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 | C1CCOC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | 334 |
104,103 | 397,792 | 680,229 | [N:1]1C(Cl)=NC(Cl)=N[C:2]=1Cl.CN.O.C(=O)([O-])O.[K+].[CH3:18][NH:19][C:20]1[N:25]=[C:24]([NH:26][CH3:27])[N:23]=[C:22](Cl)[N:21]=1>C(#N)C>[CH3:18][NH:19][C:20]1[N:25]=[C:24]([NH:26][CH3:27])[N:23]=[C:22]([NH:1][CH3:2])[N:21]=1 | |f:3.4| | US06878824B2_00063 | 2,005 | CC#N.Cl[c:3]1[n:4][c:5]([NH:6][CH3:7])[n:8][c:9]([NH:10][CH3:11])[n:12]1.Clc1nc(Cl)nc(Cl)n1.O.O=C([O-])O.[CH3:1][NH2:2].[K+]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][CH3:7])[n:8][c:9]([NH:10][CH3:11])[n:12]1 | 0.32263 | CC#N.CN.CNc1nc(Cl)nc(NC)n1.Clc1nc(Cl)nc(Cl)n1.O.O=C([O-])O~[K+]>>CNc1nc(NC)nc(NC)n1 | CC#N.CN.CNc1nc(Cl)nc(NC)n1.Clc1nc(Cl)nc(Cl)n1.O.O=C([O-])O.[K+]>>CNc1nc(NC)nc(NC)n1 | US06878824B2_00063grants | 178a94391df12b20ca7e30331939d596c58c1c7dda5dd13a9141bc17 | CC#N.Cl[c:3]1[n:4][c:5]([NH:6][CH3:7])[n:8][c:9]([NH:10][CH3:11])[n:12]1.Clc1nc(Cl)nc(Cl)n1.O.O=C([O-])O.[CH3:1][NH2:2].[K+] | [CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][CH3:7])[n:8][c:9]([NH:10][CH3:11])[n:12]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3]:[c:4]:[#7;a:5])-[NH;D2;+0:7]-[C;D1;H3:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]:[c:4]:[#7;a:5]).([C;D1;H3:6]-[NH2;D1;+0:7]) | 0b588855c6f0ec8e6e2a3fd38e0eeb9f125fc40378b70cf60a109be1 | 1 | 1 | CC#N.Clc1nc(Cl)nc(Cl)n1.O.O=C([O-])O.[K+] | 578 |
374,478 | 834,523 | null | [CH3:1][C:2]1[NH:3][C:4](=[O:23])[N:5]([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([N:13]=[CH:14][N:15]=2)[CH:12]=1.CN(C)C=O.CC(C)([O-])C.[K+].[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40]Br>>[N:15]1[CH:14]=[N:13][N:11]2[CH:12]=[C:7]([C:6]3[N:5]([C:16]4[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=4)[C:4](=[O:23])[N:3]([CH2:40][C:39]4[CH:42]=[CH:43][CH:44]=[C:37]([O:36][CH3:35])[CH:38]=4)[C:2]=3[CH3:1])[CH:8]=[CH:9][C:10]=12 | |f:2.3| | US20100035918A1_0246 | 2,010 | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32]1.CC(C)(C)[O-].CN(C)C=O.[K+].[nH:9]1[c:10]([CH3:11])[c:12](-[c:13]2[cH:14][cH:15][c:16]3[n:17][cH:18][n:19][n:20]3[cH:21]2)[n:22](-[c:23]2[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]2)[c:30]1=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10]([CH3:11])[c:12](-[c:13]3[cH:14][cH:15][c:16]4[n:17][cH:18][n:19][n:20]4[cH:21]3)[n:22](-[c:23]3[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]3)[c:30]2=[O:31])[cH:32]1 | 0.959039 | CC(C)(C)[O-]~[K+].CN(C)C=O.COc1cccc(CBr)c1.Cc1cccc(-n2c(-c3ccc4ncnn4c3)c(C)[nH]c2=O)c1>>COc1cccc(Cn2c(C)c(-c3ccc4ncnn4c3)n(-c3cccc(C)c3)c2=O)c1 | CC(C)(C)[O-].CN(C)C=O.COc1cccc(CBr)c1.Cc1cccc(-n2c(-c3ccc4ncnn4c3)c(C)[nH]c2=O)c1.[K+]>>COc1cccc(Cn2c(C)c(-c3ccc4ncnn4c3)n(-c3cccc(C)c3)c2=O)c1 | US20100035918A1_0246apps | c29de2d6f875cbd015beb39d38c076b41e1231ec52ebc9c505b57114 | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32]1.CC(C)(C)[O-].CN(C)C=O.[K+].[nH:9]1[c:10]([CH3:11])[c:12](-[c:13]2[cH:14][cH:15][c:16]3[n:17][cH:18][n:19][n:20]3[cH:21]2)[n:22](-[c:23]2[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]2)[c:30]1=[O:31] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10]([CH3:11])[c:12](-[c:13]3[cH:14][cH:15][c:16]4[n:17][cH:18][n:19][n:20]4[cH:21]3)[n:22](-[c:23]3[cH:24][cH:25][cH:26][c:27]([CH3:28])[cH:29]3)[c:30]2=[O:31])[cH:32]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) | 15f2f3fc3dcf0ea125b7a75c0a023470d5614cdcd7950e6190ace0d2 | 1 | 1 | CC(C)(C)[O-].CN(C)C=O.[K+] | 593 |
288,396 | 939,979 | 1,576,845 | [C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][C:18]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[Pd].CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:20]([NH2:21])=[CH:19][C:18]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:17][N:16]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:3])[CH3:2] | null | US08952004B2_0238 | 2,015 | CCOC(C)=O.CO.O=[N+:24]([O-])[c:23]1[c:14]([N:13]2[CH2:12][CH2:11][CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]2)[n:15][cH:16][c:17]([S:18]([CH3:19])(=[O:20])=[O:21])[cH:22]1.[Pd]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][cH:16][c:17]([S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[NH2:24])[CH2:25][CH2:26]1 | 0.242364 | CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2[N+](=O)[O-])CC1.CCOC(C)=O.CO.[Pd]>>CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2N)CC1 | CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2[N+](=O)[O-])CC1.CCOC(C)=O.CO.[Pd]>>CC(C)(C)OC(=O)NCC1CCN(c2ncc(S(C)(=O)=O)cc2N)CC1 | US08952004B2_0238grants | 9f7690a80ef2a76c32b24c017836768559c1d2c6b9b7c676af067f4c | CCOC(C)=O.CO.O=[N+:24]([O-])[c:23]1[c:14]([N:13]2[CH2:12][CH2:11][CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]2)[n:15][cH:16][c:17]([S:18]([CH3:19])(=[O:20])=[O:21])[cH:22]1.[Pd] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][cH:16][c:17]([S:18]([CH3:19])(=[O:20])=[O:21])[cH:22][c:23]2[NH2:24])[CH2:25][CH2:26]1 | ([#7;a:4]:[c:3]:[c:2]-[NH2;D1;+0:1])>>(O=[N+;H0;D3:1](-[O-])-[c:2]:[c:3]:[#7;a:4]) | e69a09e0931e7bc26f571c5e2ed13b773c90943f0f6753349e287e32 | 1 | 1 | CCOC(C)=O.CO.[Pd] | 269 |
200,156 | 683,153 | 1,127,082 | [BH4-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:19]([C:24]3[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=3)=[N:20][CH:21]=[CH:22][N:23]=2)=[CH:15][C:14]=1[F:33].[Cl-].[NH4+].O>CO>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:19]([C:24]3[CH2:29][CH2:28][CH2:27][CH:26]([OH:30])[CH:25]=3)=[N:20][CH:21]=[CH:22][N:23]=2)=[CH:15][C:14]=1[F:33] | |f:0.1,3.4| | US08053438B2_0823 | 2,011 | CO.O.[BH4-].[Cl-].[NH4+].[Na+].[O:1]=[C:2]1[CH:3]=[C:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][c:12]2[cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[s:25]3)[c:26]([F:27])[cH:28]2)[CH2:29][CH2:30][CH2:31]1>>[OH:1][CH:2]1[CH:3]=[C:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][c:12]2[cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[s:25]3)[c:26]([F:27])[cH:28]2)[CH2:29][CH2:30][CH2:31]1 | 0.966282 | CO.O.O=C1C=C(c2nccnc2Oc2ccc(Nc3nc4ccccc4s3)c(F)c2)CCC1.[BH4-]~[Na+].[Cl-]~[NH4+]>>OC1C=C(c2nccnc2Oc2ccc(Nc3nc4ccccc4s3)c(F)c2)CCC1 | CO.O.O=C1C=C(c2nccnc2Oc2ccc(Nc3nc4ccccc4s3)c(F)c2)CCC1.[BH4-].[Cl-].[NH4+].[Na+]>>OC1C=C(c2nccnc2Oc2ccc(Nc3nc4ccccc4s3)c(F)c2)CCC1 | US08053438B2_0823grants | 893402b21ff42549165303b305f4e9d1d306ffe74548805d047eaace | CO.O.[BH4-].[Cl-].[NH4+].[Na+].[O:1]=[C:2]1[CH:3]=[C:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][c:12]2[cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[s:25]3)[c:26]([F:27])[cH:28]2)[CH2:29][CH2:30][CH2:31]1 | [OH:1][CH:2]1[CH:3]=[C:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][c:12]2[cH:13][cH:14][c:15]([NH:16][c:17]3[n:18][c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[s:25]3)[c:26]([F:27])[cH:28]2)[CH2:29][CH2:30][CH2:31]1 | ([C:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[C:4]=[C:5])>>([C:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]=[C:5]) | 17f70e7f971d2010542eb4f996f342da52388ca46d125dc1e5a0f0a2 | 1 | 1 | CO.O.[BH4-].[Cl-].[NH4+].[Na+] | 288 |
110,105 | 414,964 | 707,981 | [NH2:1][CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[OH:4].[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH:2]([NH:1][C:30](=[O:31])[CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1 | |f:2.3| | US06982348B2_0582 | 2,006 | CCOC(C)=O.Cl[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O.O=C([O-])O.[NH2:10][CH:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1.[Na+]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][CH:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1 | 0.274219 | CCOC(C)=O.NC(Cc1ccc(C(F)(F)F)cc1)C(O)c1ccc(F)cc1.O.O=C(Cl)Cc1ccccc1.O=C([O-])O~[Na+]>>O=C(Cc1ccccc1)NC(Cc1ccc(C(F)(F)F)cc1)C(O)c1ccc(F)cc1 | CCOC(C)=O.NC(Cc1ccc(C(F)(F)F)cc1)C(O)c1ccc(F)cc1.O.O=C(Cl)Cc1ccccc1.O=C([O-])O.[Na+]>>O=C(Cc1ccccc1)NC(Cc1ccc(C(F)(F)F)cc1)C(O)c1ccc(F)cc1 | US06982348B2_0582grants | 9bf2d6700f6a85fdbb75fd7ed2035ebb284c00edae71711ef03b8169 | CCOC(C)=O.Cl[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.O.O=C([O-])O.[NH2:10][CH:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1.[Na+] | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][CH:11]([CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[CH:23]([OH:24])[c:25]1[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | CCOC(C)=O.O.O=C([O-])O.[Na+] | 45 |
134,329 | 488,116 | 822,224 | [NH2:1][CH2:2][C@@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>>[NH2:16][C:15]1[C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8][N:7]([C@@H:5]3[CH2:4][C@H:3]([CH2:2][NH:1][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:6]3)[C:11]=2[N:12]=[CH:13][N:14]=1 | null | US07326699B2_0312 | 2,008 | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][CH2:8][C@H:9]1[CH2:10][C@@H:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[c:29]3[c:30]([NH2:31])[n:32][cH:33][n:34][c:35]23)[CH2:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][C@H:9]1[CH2:10][C@@H:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[c:29]3[c:30]([NH2:31])[n:32][cH:33][n:34][c:35]23)[CH2:36]1 | 0.373093 | CC(C)(C)C(=O)Cl.NC[C@@H]1C[C@H](n2cc(-c3cccc(OCc4ccccc4)c3)c3c(N)ncnc32)C1>>CC(C)(C)C(=O)NC[C@H]1C[C@@H](n2cc(-c3cccc(OCc4ccccc4)c3)c3c(N)ncnc32)C1 | CC(C)(C)C(=O)Cl.NC[C@@H]1C[C@H](n2cc(-c3cccc(OCc4ccccc4)c3)c3c(N)ncnc32)C1>>CC(C)(C)C(=O)NC[C@H]1C[C@@H](n2cc(-c3cccc(OCc4ccccc4)c3)c3c(N)ncnc32)C1 | US07326699B2_0312grants | 45201db3cdd777540e6ed4de5dc1ee232b15ae79a04a99176bb3e3e7 | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][CH2:8][C@H:9]1[CH2:10][C@@H:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[c:29]3[c:30]([NH2:31])[n:32][cH:33][n:34][c:35]23)[CH2:36]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH2:8][C@H:9]1[CH2:10][C@@H:11]([n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28]3)[c:29]3[c:30]([NH2:31])[n:32][cH:33][n:34][c:35]23)[CH2:36]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | null | 45 |
266,637 | 877,353 | 1,460,491 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=[C:10]([C:20]([OH:22])=O)[CH:9]=2)=[CH:4][C:3]=1[CH3:23].[CH3:24][O:25][C:26]1[CH:30]=[C:29]([CH2:31][NH2:32])[O:28][N:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][C:16]([F:19])([F:17])[F:18])=[CH:12][N:11]=[C:10]([C:20]([NH:32][CH2:31][C:29]3[O:28][N:27]=[C:26]([O:25][CH3:24])[CH:30]=3)=[O:22])[CH:9]=2)=[CH:4][C:3]=1[CH3:23] | null | US08729105B2_0598 | 2,014 | O[C:8](=[O:9])[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[cH:28][n:29]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][NH2:7])[o:30][n:31]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[c:18]([CH3:19])[cH:20]3)[c:21]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[cH:28][n:29]2)[o:30][n:31]1 | 0.267704 | COc1cc(CN)on1.Cc1cc(-c2cc(C(=O)O)ncc2OCC(F)(F)F)ccc1Cl>>COc1cc(CNC(=O)c2cc(-c3ccc(Cl)c(C)c3)c(OCC(F)(F)F)cn2)on1 | COc1cc(CN)on1.Cc1cc(-c2cc(C(=O)O)ncc2OCC(F)(F)F)ccc1Cl>>COc1cc(CNC(=O)c2cc(-c3ccc(Cl)c(C)c3)c(OCC(F)(F)F)cn2)on1 | US08729105B2_0598grants | db2652e9ad335ea783510d87314009cf2ce76075fac1823bc9c4cc47 | O[C:8](=[O:9])[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[c:18]([CH3:19])[cH:20]2)[c:21]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[cH:28][n:29]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][NH2:7])[o:30][n:31]1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[c:18]([CH3:19])[cH:20]3)[c:21]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])[cH:28][n:29]2)[o:30][n:31]1 | ([#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 | null | 137 |
371,496 | 786,176 | null | C(O[C:6]([N:8](C)[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]1[CH3:25])=O)(C)(C)C.Cl>CO>[CH3:25][C@H:10]1[C@H:9]([NH:8][CH3:6])[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16] | null | US20090275570A1_0393 | 2,009 | CC(C)(C)OC(=O)[N:2]([CH3:1])[C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@H:18]1[CH3:19].CO.Cl>>[CH3:1][NH:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@H:18]1[CH3:19] | 0.884763 | CO.C[C@H]1[C@H](N(C)C(=O)OC(C)(C)C)CCCN1C(=O)OCc1ccccc1.Cl>>CN[C@@H]1CCCN(C(=O)OCc2ccccc2)[C@H]1C | CO.C[C@H]1[C@H](N(C)C(=O)OC(C)(C)C)CCCN1C(=O)OCc1ccccc1.Cl>>CN[C@@H]1CCCN(C(=O)OCc2ccccc2)[C@H]1C | US20090275570A1_0393apps | 2b76bb5b6e30e9edd3899dcfa794792c6688d85a53af2122c4379c59 | CC(C)(C)OC(=O)[N:2]([CH3:1])[C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@H:18]1[CH3:19].CO.Cl | [CH3:1][NH:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@H:18]1[CH3:19] | ([C:2]-[NH;D2;+0:1]-[C;D1;H3:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C;D1;H3:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | CO.Cl | 575 |
91,576 | 359,855 | 613,191 | [CH2:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([NH2:22])=[O:21])[N:17]=[CH:16]1)[CH2:12][CH2:13][OH:14])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([NH2:22])=[O:21])[N:17]=[CH:16]1)[CH2:12][CH2:13][O:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | null | US06596738B1_ | 2,003 | CCN(CC)CC.ClCCl.Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][C@H:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]([CH2:12][CH2:13][OH:14])[n:19]1[cH:20][n:21][c:22]([C:23]([NH2:24])=[O:25])[cH:26]1>>[CH3:1][C@H:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]([CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19]1[cH:20][n:21][c:22]([C:23]([NH2:24])=[O:25])[cH:26]1 | 0.517394 | CCN(CC)CC.CS(=O)(=O)Cl.C[C@H](OCc1ccccc1)[C@@H](CCO)n1cnc(C(N)=O)c1.ClCCl>>C[C@H](OCc1ccccc1)[C@@H](CCOS(C)(=O)=O)n1cnc(C(N)=O)c1 | CCN(CC)CC.CS(=O)(=O)Cl.C[C@H](OCc1ccccc1)[C@@H](CCO)n1cnc(C(N)=O)c1.ClCCl>>C[C@H](OCc1ccccc1)[C@@H](CCOS(C)(=O)=O)n1cnc(C(N)=O)c1 | US06596738B1_grants | bda0906b0f8c2fe2120889722b6c06f3916821fe2ba548750aa045e5 | CCN(CC)CC.ClCCl.Cl[S:15]([CH3:16])(=[O:17])=[O:18].[CH3:1][C@H:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]([CH2:12][CH2:13][OH:14])[n:19]1[cH:20][n:21][c:22]([C:23]([NH2:24])=[O:25])[cH:26]1 | [CH3:1][C@H:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C@@H:11]([CH2:12][CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19]1[cH:20][n:21][c:22]([C:23]([NH2:24])=[O:25])[cH:26]1 | ([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(CC)CC.ClCCl | 0 |
22,808 | 108,719 | 175,825 | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[C:13]([F:14])([F:15])[F:16] | null | US04749813_ | 1,988 | CO.O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13].[Ni]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | 0.287401 | CC(C)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1.CO.[Ni]>>CC(C)c1ccc(N)c(C(F)(F)F)c1 | CC(C)c1ccc([N+](=O)[O-])c(C(F)(F)F)c1.CO.[Ni]>>CC(C)c1ccc(N)c(C(F)(F)F)c1 | US04749813_grants | 44b82c0c3abe4f3fe0c6f37d523da65ac4e1f264148b5d79a2b38214 | CO.O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13].[Ni] | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Ni] | 1 |
85,983 | 343,852 | 586,964 | [CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:15]=[CH:16][C:17]=1[Cl:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([NH:40][C:41](OC2C=CC=CC=2)=[O:42])[C:27](=[CH:38][CH:39]=1)[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([S:19]([NH:22][C:41]([NH:40][C:26]2[CH:25]=[C:24]([Cl:23])[CH:39]=[CH:38][C:27]=2[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[O:42])(=[O:21])=[O:20])[CH:15]=[CH:16][C:17]=1[Cl:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US06500835B2_ | 2,002 | [NH2:21][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]2[C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)cc1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:21][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42]1 | 0.343919 | NS(=O)(=O)c1ccc(Cl)c(NC(=O)OCc2ccccc2)c1.O=C(Nc1cc(Cl)ccc1C(=O)OCc1ccccc1)Oc1ccccc1>>O=C(Nc1cc(Cl)ccc1C(=O)OCc1ccccc1)NS(=O)(=O)c1ccc(Cl)c(NC(=O)OCc2ccccc2)c1 | NS(=O)(=O)c1ccc(Cl)c(NC(=O)OCc2ccccc2)c1.O=C(Nc1cc(Cl)ccc1C(=O)OCc1ccccc1)Oc1ccccc1>>O=C(Nc1cc(Cl)ccc1C(=O)OCc1ccccc1)NS(=O)(=O)c1ccc(Cl)c(NC(=O)OCc2ccccc2)c1 | US06500835B2_grants | 9717680d977f661c41d639d57e5f4494da0ef5d73f16d1016d9b0aba | [NH2:21][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]2[C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)cc1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][c:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:21][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][c:28]([Cl:29])[c:30]([NH:31][C:32](=[O:33])[O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:42]1 | ([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8])>>([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-c1:c:c:c:c:c:1).([NH2;D1;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8]) | e3a5f56e4cb52c390952a4bd41f709e2d3c3f49b8b3af4a47445d899 | 1 | 1 | null | 690 |
84,776 | 339,384 | 579,041 | [CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:24]1[NH:29][C:28](=[O:30])[C:27]2=[C:31]([CH3:39])[N:32]=[C:33]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:26]2[N:25]=1)[CH3:2].[OH-].[Na+].O>CO.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:24]1[NH:29][C:28](=[O:30])[C:27]2=[C:31]([CH3:39])[N:32]=[C:33]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[N:26]2[N:25]=1)[CH3:2] | |f:1.2,4.5| | US06476029B1_ | 2,002 | CC[O:17][C:15]([CH:14]1[CH2:13][CH2:12][N:11]([S:8]([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:21](-[c:22]3[n:23][n:24]4[c:25]([CH:26]5[CH2:27][CH2:28][CH2:29][CH2:30]5)[n:31][c:32]([CH3:33])[c:34]4[c:35](=[O:36])[nH:37]3)[cH:20]2)(=[O:9])=[O:10])[CH2:19][CH2:18]1)=[O:16].CO.O.O.[Na+].[OH-]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[OH:17])[CH2:18][CH2:19]2)[cH:20][c:21]1-[c:22]1[n:23][n:24]2[c:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[n:31][c:32]([CH3:33])[c:34]2[c:35](=[O:36])[nH:37]1 | 0.500976 | CCOC(=O)C1CCN(S(=O)(=O)c2ccc(OCC)c(-c3nn4c(C5CCCC5)nc(C)c4c(=O)[nH]3)c2)CC1.CO~O.O.[Na+]~[OH-]>>CCOc1ccc(S(=O)(=O)N2CCC(C(=O)O)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | CCOC(=O)C1CCN(S(=O)(=O)c2ccc(OCC)c(-c3nn4c(C5CCCC5)nc(C)c4c(=O)[nH]3)c2)CC1.CO.O.O.[Na+].[OH-]>>CCOc1ccc(S(=O)(=O)N2CCC(C(=O)O)CC2)cc1-c1nn2c(C3CCCC3)nc(C)c2c(=O)[nH]1 | US06476029B1_grants | 41dce77f1683d588cb9d40395654f1cee21ce570239f659962082acc | CC[O:17][C:15]([CH:14]1[CH2:13][CH2:12][N:11]([S:8]([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:21](-[c:22]3[n:23][n:24]4[c:25]([CH:26]5[CH2:27][CH2:28][CH2:29][CH2:30]5)[n:31][c:32]([CH3:33])[c:34]4[c:35](=[O:36])[nH:37]3)[cH:20]2)(=[O:9])=[O:10])[CH2:19][CH2:18]1)=[O:16].CO.O.O.[Na+].[OH-] | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]2[CH2:12][CH2:13][CH:14]([C:15](=[O:16])[OH:17])[CH2:18][CH2:19]2)[cH:20][c:21]1-[c:22]1[n:23][n:24]2[c:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[n:31][c:32]([CH3:33])[c:34]2[c:35](=[O:36])[nH:37]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 | CO.O.O.[Na+].[OH-] | 7 |
205,403 | 697,551 | 1,149,065 | [Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16]>ClCCl.CCOCC>[I:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16] | |f:0.1| | US08097238B2_0230 | 2,012 | CCOCC.ClCCl.O=[Cr](=O)([O-])Cl.[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9].c1cc[nH+]cc1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9] | 0.948423 | CCOCC.ClCCl.O=[Cr](=O)([O-])Cl~c1cc[nH+]cc1.OCc1ccccc1I>>O=Cc1ccccc1I | CCOCC.ClCCl.O=[Cr](=O)([O-])Cl.OCc1ccccc1I.c1cc[nH+]cc1>>O=Cc1ccccc1I | US08097238B2_0230grants | d64d2477e318b26c12082525ab57bc8b042e0ac45c43c6e0ecdf8714 | CCOCC.ClCCl.O=[Cr](=O)([O-])Cl.[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9].c1cc[nH+]cc1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[I:9] | ([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3])>>([OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]) | 6f544a9b286c4786b46429a74b4a72e536e22ba10273cfcd1d3d737e | 1 | 1 | CCOCC.ClCCl.O=[Cr](=O)([O-])Cl.c1cc[nH+]cc1 | 179 |
185,029 | 640,646 | 1,059,330 | [CH3:1][CH:2]1[C:6]2[NH:7][C:8]([C:10]([O:12]CC)=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1.[OH-].[Li+].C(O)C>C1COCC1>[CH3:1][CH:2]1[C:6]2[NH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1 | |f:1.2| | US07902252B2_0805 | 2,011 | C1CCOC1.CCO.CC[O:10][C:8]([c:7]1[cH:6][c:5]2[c:12]([nH:11]1)[CH:2]([CH3:1])[CH2:3][CH2:4]2)=[O:9].[Li+].[OH-]>>[CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[nH:11][c:12]21 | 0.96274 | C1CCOC1.CCO.CCOC(=O)c1cc2c([nH]1)C(C)CC2.[Li+]~[OH-]>>CC1CCc2cc(C(=O)O)[nH]c21 | C1CCOC1.CCO.CCOC(=O)c1cc2c([nH]1)C(C)CC2.[Li+].[OH-]>>CC1CCc2cc(C(=O)O)[nH]c21 | US07902252B2_0805grants | b57767077f5a309a35b5080c42959a2b98325fbcd4d89f60126f1dce | C1CCOC1.CCO.CC[O:10][C:8]([c:7]1[cH:6][c:5]2[c:12]([nH:11]1)[CH:2]([CH3:1])[CH2:3][CH2:4]2)=[O:9].[Li+].[OH-] | [CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[nH:11][c:12]21 | ([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 | C1CCOC1.CCO.[Li+].[OH-] | 171 |
170,767 | 598,875 | 992,384 | C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[C:9]([F:21])[CH:8]=1.CN(C)[CH:24]=[O:25]>O1CCCC1>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([F:21])[CH:10]=1)[CH:24]=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | null | US07745438B2_0789 | 2,010 | Br[c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1.C1CCOC1.CN(C)[CH:2]=[O:1].[Li]CCCC>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | 0.873672 | C1CCOC1.CN(C)C=O.Fc1cc(Br)cc(OCc2ccccc2)c1.[Li]CCCC>>O=Cc1cc(F)cc(OCc2ccccc2)c1 | C1CCOC1.CN(C)C=O.Fc1cc(Br)cc(OCc2ccccc2)c1.[Li]CCCC>>O=Cc1cc(F)cc(OCc2ccccc2)c1 | US07745438B2_0789grants | 3b93f0d1b9feb0fd2f090f8b9a0f0a1d05d8929d03cfd2fea78cfa04 | Br[c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1.C1CCOC1.CN(C)[CH:2]=[O:1].[Li]CCCC | [O:1]=[CH:2][c:3]1[cH:4][c:5]([F:6])[cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | ([O;D1;H0:5]=[CH;D2;+0:4]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-N(-C)-[CH;D2;+0:4]=[O;D1;H0:5]) | 7de7096faf6d2371b3e516981e65b03fd948d01c7a7c47ffeee407fc | 1 | 1 | C1CCOC1.[Li]CCCC | 638 |
217,698 | 732,253 | 1,206,452 | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]2 | null | US08211923B2_0303 | 2,012 | CO.O=[N+:14]([O-])[c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2.[Pd]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][c:13]([NH2:14])[cH:15][cH:16][c:17]21 | 0.455859 | CC(C)(C)OC(=O)N1CCc2cc([N+](=O)[O-])ccc21.CO.[Pd]>>CC(C)(C)OC(=O)N1CCc2cc(N)ccc21 | CC(C)(C)OC(=O)N1CCc2cc([N+](=O)[O-])ccc21.CO.[Pd]>>CC(C)(C)OC(=O)N1CCc2cc(N)ccc21 | US08211923B2_0303grants | c078d9ccfdfd840fe57bbb391b48ac8a6e859be5fb63387b6427ca4a | CO.O=[N+:14]([O-])[c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2.[Pd] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][c:13]([NH2:14])[cH:15][cH:16][c:17]21 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
417,828 | 1,736,405 | null | [C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13](=[O:33])[CH2:14][C:15]1([N:26]2[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:33])[CH2:14][C:15]1([N:26]2[CH2:31][CH2:30][CH:29]([NH:10][C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:28][CH2:27]2)[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18]1 | |f:3.4| | US20150225394A1_0556 | 2,015 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O=[C:10]1[CH2:9][CH2:8][N:7]([C:6]2([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]2)[CH2:22][CH2:21]1.[NH2:11][C@@H:12]1[CH2:13][C@H:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[Na+]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1([N:7]2[CH2:8][CH2:9][CH:10]([NH:11][C@@H:12]3[CH2:13][C@H:14]3[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1 | 0.333225 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].COC(=O)CC1(N2CCC(=O)CC2)CN(C(=O)OC(C)(C)C)C1.ClCCl.N[C@@H]1C[C@H]1c1ccccc1>>COC(=O)CC1(N2CCC(N[C@@H]3C[C@H]3c3ccccc3)CC2)CN(C(=O)OC(C)(C)C)C1 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.COC(=O)CC1(N2CCC(=O)CC2)CN(C(=O)OC(C)(C)C)C1.ClCCl.N[C@@H]1C[C@H]1c1ccccc1.[Na+]>>COC(=O)CC1(N2CCC(N[C@@H]3C[C@H]3c3ccccc3)CC2)CN(C(=O)OC(C)(C)C)C1 | US20150225394A1_0556apps | 0286fd624b521e7accd9642dfab5df49b9ded94af9b9b2c1da688331 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O=[C:10]1[CH2:9][CH2:8][N:7]([C:6]2([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]2)[CH2:22][CH2:21]1.[NH2:11][C@@H:12]1[CH2:13][C@H:14]1[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[Na+] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1([N:7]2[CH2:8][CH2:9][CH:10]([NH:11][C@@H:12]3[CH2:13][C@H:14]3[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32]1 | ([C:4]-[NH;D2;+0:5]-[CH;D3;+0:1](-[C:2])-[C:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[C:3]).([C:4]-[NH2;D1;+0:5]) | 67be25fd3ed7bf7f205940372151b70bd780167c6e07893adbc37ca7 | 1 | 1 | CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.[Na+] | 236 |
296,340 | 964,945 | 1,623,585 | [N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1 | |f:1.2| | US09045485B2_0345 | 2,015 | CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1.O.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1 | 0.903508 | CO.COC(=O)c1cccc(OCCN2CCCC2)c1.O.[Na+]~[OH-]>>O=C(O)c1cccc(OCCN2CCCC2)c1 | CO.COC(=O)c1cccc(OCCN2CCCC2)c1.O.[Na+].[OH-]>>O=C(O)c1cccc(OCCN2CCCC2)c1 | US09045485B2_0345grants | 2af3ffe0a1602379b24b54c8216924191e81a7306b99beaaa3414b3f | CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1.O.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]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 |
392,115 | 1,192,686 | null | I[C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>[C:12]1([C:2]2[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=2)[C:6]#[N:7])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1 | |f:2.3.4,6.7.8.9.10| | US20120068123A1_0421 | 2,012 | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CCOCC.I[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:14]([C:15]#[N:16])[cH:13]1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[Cs+].[Cs+].[Pd].[Pd]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[C:15]#[N:16] | 0.868369 | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CCOCC.N#Cc1ccc(I)cc1C#N.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~[Pd]~[Pd].O=C([O-])[O-]~[Cs+]~[Cs+].OB(O)c1ccccc1>>N#Cc1ccc(-c2ccccc2)cc1C#N | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CCOCC.N#Cc1ccc(I)cc1C#N.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].OB(O)c1ccccc1.[Cs+].[Cs+].[Pd].[Pd]>>N#Cc1ccc(-c2ccccc2)cc1C#N | US20120068123A1_0421apps | 8d696c9fd90e13e90d0975216243167c1ff57ce8f83a2357e27775d8 | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CCOCC.I[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:14]([C:15]#[N:16])[cH:13]1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[Cs+].[Cs+].[Pd].[Pd] | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1[C:15]#[N:16] | ([c:5]:[c;H0;D3;+0:4](:[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]) | 7dd39e88343158d749428576676d52834a98797b3952df04cfe843cf | 0.5 | 2 | CC(C)(C)P(C(C)(C)C)C(C)(C)C.CCOCC.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd] | 855 |
306,418 | 996,181 | 1,682,795 | [CH3:1][CH2:2][O-:3].[Na+].CCO.Cl[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1>O>[CH2:2]([O:3][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)[CH3:1] | |f:0.1| | US09168245B2_0244 | 2,015 | CC[O-].Cl[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1.O.[CH3:1][CH2:2][OH:3].[Na+]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | 0.903938 | CCO.CC[O-]~[Na+].Cc1ccc(CCl)cc1[N+](=O)[O-].O>>CCOCc1ccc(C)c([N+](=O)[O-])c1 | CCO.CC[O-].Cc1ccc(CCl)cc1[N+](=O)[O-].O.[Na+]>>CCOCc1ccc(C)c([N+](=O)[O-])c1 | US09168245B2_0244grants | 97edd4d92ed266d2ba278b43d460c60434b4b63eebdd7bcf80e88017 | CC[O-].Cl[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1.O.[CH3:1][CH2:2][OH:3].[Na+] | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(Cl-[CH2;D2;+0:1]-[c:2]).([C:3]-[OH;D1;+0:4]) | b5e2d07bf20d348d689f458c42b9c3430d20b3d9da8a412578e36c92 | 1 | 1 | CC[O-].O.[Na+] | 208 |
398,387 | 1,326,997 | null | Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH3:17]>CS(C)=O.O>[CH3:12][O:13][CH2:14][CH2:15][N:16]([CH3:17])[C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1 | null | US20130029961A1_0733 | 2,013 | CS(C)=O.Cl[c:7]1[cH:8][cH:9][c:10]([CH:11]([CH3:12])[C:13]#[N:14])[cH:15][n:16]1.O.[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]([CH3:12])[C:13]#[N:14])[cH:15][n:16]1 | 0.995555 | CC(C#N)c1ccc(Cl)nc1.CNCCOC.CS(C)=O.O>>COCCN(C)c1ccc(C(C)C#N)cn1 | CC(C#N)c1ccc(Cl)nc1.CNCCOC.CS(C)=O.O>>COCCN(C)c1ccc(C(C)C#N)cn1 | US20130029961A1_0733apps | 61c2c4d1a3072716eed7925e0391d04593cf9bb17fcd8cfa374228a0 | CS(C)=O.Cl[c:7]1[cH:8][cH:9][c:10]([CH:11]([CH3:12])[C:13]#[N:14])[cH:15][n:16]1.O.[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6] | [CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]([CH3:12])[C:13]#[N:14])[cH:15][n:16]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C;D1;H3:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | d775cf39c89817610201eb77d7f2c05750999ab6870ec4bcf35a0a78 | 1 | 1 | CS(C)=O.O | 220 |
8,406 | 42,934 | 68,882 | [CH2:1]([CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(C1C=CC(O)=CC=1)CC.[O-]CC.[Na+]>[Ni].C(O)C>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)[CH2:2][CH3:3] | |f:2.3| | US04211666_ | 1,980 | CCCc1ccc(O)cc1.CCO.CC[O-].[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][C:7](=[O:8])[CH2:9][CH2:10]1.[Na+].[Ni]>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10]1 | 0.794979 | CCCC1CCC(=O)CC1.CCCc1ccc(O)cc1.CCO.CC[O-]~[Na+].[Ni]>>CCCC1CCC(O)CC1 | CCCC1CCC(=O)CC1.CCCc1ccc(O)cc1.CCO.CC[O-].[Na+].[Ni]>>CCCC1CCC(O)CC1 | US04211666_grants | bf18d5402ae326abe178a54b82011e814a31552766a977405e46a135 | CCCc1ccc(O)cc1.CCO.CC[O-].[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][C:7](=[O:8])[CH2:9][CH2:10]1.[Na+].[Ni] | [CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10]1 | ([C:1]-[CH;D3;+0:2](-[C:3])-[OH;D1;+0:4])>>([C:1]-[C;H0;D3;+0:2](-[C:3])=[O;H0;D1;+0:4]) | 0fb396942a5bc824558e6936c3618c2e342b489a89eccebed032da69 | 1 | 1 | CCCc1ccc(O)cc1.CCO.CC[O-].[Na+].[Ni] | 91 |
20,109 | 96,820 | 157,217 | [NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:5][C:2]([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])([CH3:6])[C:3]#[N:4] | null | US04652556_ | 1,987 | CCN(CC)CC.ClCCl.Cl[S:7]([CH3:8])(=[O:9])=[O:10].[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[NH2:6]>>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[NH:6][S:7]([CH3:8])(=[O:9])=[O:10] | 0.576524 | CC(C)(N)C#N.CCN(CC)CC.CS(=O)(=O)Cl.ClCCl>>CC(C)(C#N)NS(C)(=O)=O | CC(C)(N)C#N.CCN(CC)CC.CS(=O)(=O)Cl.ClCCl>>CC(C)(C#N)NS(C)(=O)=O | US04652556_grants | cfdddde8d3d675a455a9cca3511868da21b86a562726f87c43557159 | CCN(CC)CC.ClCCl.Cl[S:7]([CH3:8])(=[O:9])=[O:10].[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[NH2:6] | [CH3:1][C:2]([CH3:3])([C:4]#[N:5])[NH:6][S:7]([CH3:8])(=[O:9])=[O:10] | ([C:5]-[NH;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]-[NH2;D1;+0:6]) | dd26373922ad1a10525dbf7c5ecf698381ad4c146b9d8d0e516b94ff | 1 | 1 | CCN(CC)CC.ClCCl | 493 |
97,791 | 378,216 | 647,678 | [F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[CH3:18][CH:19]([CH3:36])[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:24]=1)=[O:21]>>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][N:33]2[CH2:34][CH2:35][CH:30]([C:25]3[CH:24]=[C:23]([NH:22][C:20](=[O:21])[CH:19]([CH3:18])[CH3:36])[CH:28]=[CH:27][C:26]=3[CH3:29])[CH2:31][CH2:32]2)=[CH:8][CH:7]=1 | null | US06727264B1_ | 2,004 | O=[CH:18][c:19]1[cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][c:27]([F:28])[c:29]([F:30])[cH:31]2)[cH:32][cH:33]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:34][CH2:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([O:23][c:24]3[cH:25][cH:26][c:27]([F:28])[c:29]([F:30])[cH:31]3)[cH:32][cH:33]2)[CH2:34][CH2:35]1 | 0.688805 | Cc1ccc(NC(=O)C(C)C)cc1C1CCNCC1.O=Cc1ccc(Oc2ccc(F)c(F)c2)cc1>>Cc1ccc(NC(=O)C(C)C)cc1C1CCN(Cc2ccc(Oc3ccc(F)c(F)c3)cc2)CC1 | Cc1ccc(NC(=O)C(C)C)cc1C1CCNCC1.O=Cc1ccc(Oc2ccc(F)c(F)c2)cc1>>Cc1ccc(NC(=O)C(C)C)cc1C1CCN(Cc2ccc(Oc3ccc(F)c(F)c3)cc2)CC1 | US06727264B1_grants | 3dc158ad15028bcc969f80de5ca65942040f4d733d4af2161aee5ffe | O=[CH:18][c:19]1[cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][c:27]([F:28])[c:29]([F:30])[cH:31]2)[cH:32][cH:33]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:34][CH2:35]1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([O:23][c:24]3[cH:25][cH:26][c:27]([F:28])[c:29]([F:30])[cH:31]3)[cH:32][cH:33]2)[CH2:34][CH2:35]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | e4209383939f49c0378a8859c2af8829f35179fef3a6302d2bd2297e | 1 | 1 | null | 567 |
165,722 | 583,108 | 969,369 | Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:12]([CH3:14])[CH3:13])[CH:6]=[CH:5]2.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=[CH2:22].C([O-])([O-])=O.[Na+].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH3:13][N:12]([CH3:14])[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:22]=[CH:21]/[C:20]3[CH:19]=[C:18]([CH3:23])[N:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]=3[CH3:15])[CH:3]=2)[CH:8]=1 | |f:2.3.4,5.6,7.8.9| | US07696227B2_0138 | 2,010 | Br[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([N:13]([CH3:14])[CH3:15])[cH:16][cH:17][c:18]2[cH:19]1.CC(=O)[O-].CC(=O)[O-].CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[CH2:6])[c:20]([CH3:21])[n:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[Cl-].[Na+].[Na+].[Pd+2]>>[CH3:1][c:2]1[cH:3][c:4](/[CH:5]=[CH:6]/[c:7]2[cH:8][cH:9][c:10]3[cH:11][c:12]([N:13]([CH3:14])[CH3:15])[cH:16][cH:17][c:18]3[cH:19]2)[c:20]([CH3:21])[n:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1 | 0.594265 | C=Cc1cc(C)n(-c2ccccc2)c1C.CC(=O)[O-]~CC(=O)[O-]~[Pd+2].CCCC[N+](CCCC)(CCCC)CCCC~[Cl-].CN(C)C=O.CN(C)c1ccc2cc(Br)ccc2c1.O=C([O-])[O-]~[Na+]~[Na+]>>Cc1cc(/C=C/c2ccc3cc(N(C)C)ccc3c2)c(C)n1-c1ccccc1 | C=Cc1cc(C)n(-c2ccccc2)c1C.CC(=O)[O-].CC(=O)[O-].CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.CN(C)c1ccc2cc(Br)ccc2c1.O=C([O-])[O-].[Cl-].[Na+].[Na+].[Pd+2]>>Cc1cc(/C=C/c2ccc3cc(N(C)C)ccc3c2)c(C)n1-c1ccccc1 | US07696227B2_0138grants | 42df206ed8c7ea37fbbc8f4e947b03ebf9b13b8625c83cf2cfcd2b10 | Br[c:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([N:13]([CH3:14])[CH3:15])[cH:16][cH:17][c:18]2[cH:19]1.CC(=O)[O-].CC(=O)[O-].CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.O=C([O-])[O-].[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[CH2:6])[c:20]([CH3:21])[n:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[Cl-].[Na+].[Na+].[Pd+2] | [CH3:1][c:2]1[cH:3][c:4](/[CH:5]=[CH:6]/[c:7]2[cH:8][cH:9][c:10]3[cH:11][c:12]([N:13]([CH3:14])[CH3:15])[cH:16][cH:17][c:18]3[cH:19]2)[c:20]([CH3:21])[n:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1 | ([C:4]=[CH;D2;+0:5]/[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]=[CH2;D1;+0:5]) | 0996d8c51008ea3b4ae6c7b138cc093a3a5afb04d5508cf0878c0251 | 0.5 | 2 | CC(=O)[O-].CC(=O)[O-].CCCC[N+](CCCC)(CCCC)CCCC.CN(C)C=O.O=C([O-])[O-].[Cl-].[Na+].[Na+].[Pd+2] | 539 |
376,774 | 876,780 | null | Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Pd]>[CH2:9]([CH:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | null | US20100119424A1_0057 | 2,010 | Br[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:20][n:19]1.[NH:6]1[CH2:7][CH2:8][CH:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1.[Pd]>>[Br:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[n:19][cH:20]1 | 0.695556 | Brc1ccc(Br)nc1.[Pd].c1ccc(CC2CCNCC2)cc1>>Brc1ccc(N2CCC(Cc3ccccc3)CC2)nc1 | Brc1ccc(Br)nc1.[Pd].c1ccc(CC2CCNCC2)cc1>>Brc1ccc(N2CCC(Cc3ccccc3)CC2)nc1 | US20100119424A1_0057apps | 7bce1992996cdb1f4f1dc953a3919617803d674cef1b6cd61ada5fbf | Br[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:20][n:19]1.[NH:6]1[CH2:7][CH2:8][CH:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18]1.[Pd] | [Br:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][CH2:18]2)[n:19][cH:20]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Br-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 276078db16d2b12b593ab106ec54f4e5950a290c90e6afbf83a4717a | 1 | 1 | [Pd] | 647 |
151,861 | 542,505 | 908,131 | [Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)C(C)C)(C)C.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1.CCOC(C)=O>CN1CCN(C)C1=O.O>[C:33]([O:32][C:30]([N:26]1[CH2:27][CH2:28][CH2:29][C@@H:24]([NH:23][C:3]2[C:2]([Cl:1])=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=2)[CH2:25]1)=[O:31])([CH3:36])([CH3:34])[CH3:35] | null | US07557127B2_1022 | 2,009 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN1CCN(C)C1=O.Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:26][c:24]1[Cl:25].O.[NH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][C@@H:11]2[CH2:12][CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]([Cl:25])[cH:26]1 | 0.334634 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.CCN(C(C)C)C(C)C.CCOC(=O)c1cnc(Cl)c(Cl)c1.CCOC(C)=O.CN1CCN(C)C1=O.O>>CCOC(=O)c1cnc(N[C@@H]2CCCN(C(=O)OC(C)(C)C)C2)c(Cl)c1 | CC(C)(C)OC(=O)N1CCC[C@@H](N)C1.CCN(C(C)C)C(C)C.CCOC(=O)c1cnc(Cl)c(Cl)c1.CCOC(C)=O.CN1CCN(C)C1=O.O>>CCOC(=O)c1cnc(N[C@@H]2CCCN(C(=O)OC(C)(C)C)C2)c(Cl)c1 | US07557127B2_1022grants | d813372f26a1eeba1176c4f102c47e9a8488e3ce608aa98f74b125e7 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN1CCN(C)C1=O.Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:26][c:24]1[Cl:25].O.[NH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][C@@H:11]2[CH2:12][CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]([Cl:25])[cH:26]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH2;D1;+0:5]) | b7dcca1715ae4f4860ce60c58aa7a841fe17b3f404fb48a132c70869 | 1 | 1 | CCN(C(C)C)C(C)C.CCOC(C)=O.CN1CCN(C)C1=O.O | 70 |
310,691 | 1,010,331 | 1,709,725 | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11](O)=[O:12])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1 | |f:1.2.3.4.5.6| | US09221790B2_0132 | 2,015 | CCOCC.O=[C:2]([OH:1])[CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | 0.637774 | CCOCC.O=C(O)Cc1c[nH]c2ccccc12.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>OCCc1c[nH]c2ccccc12 | CCOCC.O=C(O)Cc1c[nH]c2ccccc12.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>OCCc1c[nH]c2ccccc12 | US09221790B2_0132grants | a9cf8f3cac8fb8748e87db1b30a1d9302ccf3c42faa459e3aa0c9a59 | CCOCC.O=[C:2]([OH:1])[CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [OH:1][CH2:2][CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12 | ([C:2]-[CH2;D2;+0:1]-[O;D1;H1:3])>>(O=[C;H0;D3;+0:1](-[C:2])-[O;D1;H1:3]) | 19ea0b41ce34ad96a8275f097d0c11f47736ca7f973cd7c4aee5b189 | 1 | 1 | CCOCC.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 231 |
279,958 | 917,129 | 1,533,489 | C([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>CO.O>[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:4]([OH:24])=[O:3])=[CH:12][CH:11]=2)=[CH:20][CH:19]=1)[CH3:23] | |f:1.2| | US08877754B2_0454 | 2,014 | CC[O:18][C:16]([CH2:15][CH2:14][c:13]1[cH:12][cH:11][c:10]([C:9]#[C:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:22][cH:21]2)[cH:20][cH:19]1)=[O:17].CO.Cl.O.[Na+].[OH-]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16](=[O:17])[OH:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | 0.837002 | CCOC(=O)CCc1ccc(C#Cc2ccc(OCC)cc2)cc1.CO.Cl.O.[Na+]~[OH-]>>CCOc1ccc(C#Cc2ccc(CCC(=O)O)cc2)cc1 | CCOC(=O)CCc1ccc(C#Cc2ccc(OCC)cc2)cc1.CO.Cl.O.[Na+].[OH-]>>CCOc1ccc(C#Cc2ccc(CCC(=O)O)cc2)cc1 | US08877754B2_0454grants | 366a5777de8ca2ddfa6e7afcd96a87e527b6e38f1bea343df6600599 | CC[O:18][C:16]([CH2:15][CH2:14][c:13]1[cH:12][cH:11][c:10]([C:9]#[C:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:22][cH:21]2)[cH:20][cH:19]1)=[O:17].CO.Cl.O.[Na+].[OH-] | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]#[C:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][C:16](=[O:17])[OH:18])[cH:19][cH:20]2)[cH:21][cH:22]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 | CO.Cl.O.[Na+].[OH-] | 7 |
230,104 | 769,474 | 1,269,034 | [CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:9]([CH3:25])([CH3:24])[CH:8]2O)(=[O:4])=[O:3].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:9]([CH3:25])([CH3:24])[CH2:8]2)(=[O:3])=[O:4] | null | US08344137B2_0653 | 2,013 | CC[SiH](CC)CC.O=C(O)C(F)(F)F.O[CH:4]1[C:2]([CH3:1])([CH3:3])[CH:16]([c:17]2[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]2)[NH:15][c:14]2[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2>>[CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]2[NH:15][CH:16]1[c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1 | 0.543747 | CC1(C)C(O)c2cc(S(C)(=O)=O)ccc2NC1c1cccc([N+](=O)[O-])c1.CC[SiH](CC)CC.O=C(O)C(F)(F)F>>CC1(C)Cc2cc(S(C)(=O)=O)ccc2NC1c1cccc([N+](=O)[O-])c1 | CC1(C)C(O)c2cc(S(C)(=O)=O)ccc2NC1c1cccc([N+](=O)[O-])c1.CC[SiH](CC)CC.O=C(O)C(F)(F)F>>CC1(C)Cc2cc(S(C)(=O)=O)ccc2NC1c1cccc([N+](=O)[O-])c1 | US08344137B2_0653grants | cdd075a5963f6575fbe2110fae7938cbe878c5c833156ffae57de0dc | CC[SiH](CC)CC.O=C(O)C(F)(F)F.O[CH:4]1[C:2]([CH3:1])([CH3:3])[CH:16]([c:17]2[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]2)[NH:15][c:14]2[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2 | [CH3:1][C:2]1([CH3:3])[CH2:4][c:5]2[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]2[NH:15][CH:16]1[c:17]1[cH:18][cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25]1 | ([C:2]-[CH2;D2;+0:1]-[c:3])>>(O-[CH;D3;+0:1](-[C:2])-[c:3]) | 7493378c004854aefa59c0deb1b1b9ed3742681f6ca783d070ee704e | 1 | 1 | CC[SiH](CC)CC.O=C(O)C(F)(F)F | 447 |
54,875 | 235,967 | 395,918 | Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:16])[CH:11]=2)[N:4]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Cl:16][C:12]1[CH:11]=[C:10]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][O:24][C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)[N:4]=2)[CH:15]=[CH:14][N:13]=1 | |f:2.3.4,6.7| | US05710106_ | 1,998 | CCCCCC.CCOC(C)=O.CN(C)C=O.Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][c:14]2[cH:15][cH:16][n:17][c:18]([Cl:19])[cH:20]2)[n:21]1.O=C([O-])[O-].[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:22][cH:23]1.[K+].[K+]>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][n:17][c:18]([Cl:19])[cH:20]3)[n:21]2)[cH:22][cH:23]1 | 0.89455 | CCCCCC~CCOC(C)=O.CN(C)C=O.ClCc1cccc(Oc2ccnc(Cl)c2)n1.O=C([O-])[O-]~[K+]~[K+].Oc1ccc(F)cc1>>Fc1ccc(OCc2cccc(Oc3ccnc(Cl)c3)n2)cc1 | CCCCCC.CCOC(C)=O.CN(C)C=O.ClCc1cccc(Oc2ccnc(Cl)c2)n1.O=C([O-])[O-].Oc1ccc(F)cc1.[K+].[K+]>>Fc1ccc(OCc2cccc(Oc3ccnc(Cl)c3)n2)cc1 | US05710106_grants | a0c635abcd9ad625c4084ea06ef2bda5f6d1c9cfc95673b66de17ac3 | CCCCCC.CCOC(C)=O.CN(C)C=O.Cl[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][c:14]2[cH:15][cH:16][n:17][c:18]([Cl:19])[cH:20]2)[n:21]1.O=C([O-])[O-].[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:22][cH:23]1.[K+].[K+] | [F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][n:17][c:18]([Cl:19])[cH:20]3)[n:21]2)[cH:22][cH:23]1 | ([#7;a:3]:[c:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5])>>(Cl-[CH2;D2;+0:1]-[c:2]:[#7;a:3]).([OH;D1;+0:4]-[c:5]) | 8ec77fc6c3e7715b8aa945dadf6af1b3ab70a216821d885b16245b73 | 1 | 1 | CCCCCC.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 616 |
137,684 | 498,822 | 839,124 | [F:1][CH:2]([F:23])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]([OH:14])=O)=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH3:22])[CH:16]=2)[CH:4]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].Cl>>[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([NH:34][C:12]([C:11]2[CH:10]=[N:9][N:8]3[C:3]([CH:2]([F:1])[F:23])=[CH:4][C:5]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH3:22])[CH:16]=4)=[N:6][C:7]=23)=[O:14])[CH:31]=[CH:32][CH:33]=1)(=[O:26])=[O:27] | null | US07378417B2_0441 | 2,008 | Cl.O[C:15]([c:14]1[cH:13][n:12][n:11]2[c:7]([CH:8]([F:9])[F:10])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([Cl:33])[cH:31][cH:30]3)[n:29][c:28]21)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH:8]([F:9])[F:10])[n:11]3[n:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27]4)[c:28]3[n:29]2)[cH:30][cH:31][c:32]1[Cl:33] | 0.350639 | CS(=O)(=O)c1cccc(N)c1.Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.Cl>>Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)Nc4cccc(S(C)(=O)=O)c4)c3n2)ccc1Cl | CS(=O)(=O)c1cccc(N)c1.Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.Cl>>Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)Nc4cccc(S(C)(=O)=O)c4)c3n2)ccc1Cl | US07378417B2_0441grants | 200a2766206c272406e2bb096632c218fdd886cc2ea7fc7e6b9de740 | Cl.O[C:15]([c:14]1[cH:13][n:12][n:11]2[c:7]([CH:8]([F:9])[F:10])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([Cl:33])[cH:31][cH:30]3)[n:29][c:28]21)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27]1 | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH:8]([F:9])[F:10])[n:11]3[n:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]4[cH:19][cH:20][cH:21][c:22]([S:23]([CH3:24])(=[O:25])=[O:26])[cH:27]4)[c:28]3[n:29]2)[cH:30][cH:31][c:32]1[Cl:33] | ([#7;a:8]:[c:7]1:[#7;a:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:10])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6]:[c:7]:1:[#7;a:8]).([NH2;D1;+0:9]-[c:10]) | c9e57783e2f564bd27ba609d29ad503bed3a706a7758103a8e21cf39 | 1 | 1 | Cl | 969 |
7,761 | 39,951 | 63,538 | [S:1]([C:5]1[CH:6]=[C:7]([C:15]([OH:17])=O)[C:8]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:14]=1)(=[O:4])(=[O:3])[NH2:2].O1CCOCC1.[N:24]1[CH:29]=[CH:28][CH:27]=[N:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.N>O.C(N(CC)CC)C>[CH2:12]1[CH2:11][O:10][C:9]2[C:8](=[C:7]([CH:6]=[C:5]([S:1](=[O:3])(=[O:4])[NH2:2])[CH:14]=2)[C:15]([N:33]2[CH2:34][CH2:35][N:30]([C:25]3[N:24]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:31][CH2:32]2)=[O:17])[O:13]1 | null | US04186135_ | 1,980 | C1COCCO1.CCN(CC)CC.N.O.O[C:10]([c:9]1[c:8]2[c:7]([cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:24]1)[O:28][CH2:27][CH2:26][O:25]2)=[O:11].[NH:12]1[CH2:13][CH2:14][N:15]([c:16]2[n:17][cH:18][cH:19][cH:20][n:21]2)[CH2:22][CH2:23]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]2[c:8]([c:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][N:15]([c:16]4[n:17][cH:18][cH:19][cH:20][n:21]4)[CH2:22][CH2:23]3)[cH:24]1)[O:25][CH2:26][CH2:27][O:28]2 | 0.43041 | C1COCCO1.CCN(CC)CC.N.NS(=O)(=O)c1cc2c(c(C(=O)O)c1)OCCO2.O.c1cnc(N2CCNCC2)nc1>>NS(=O)(=O)c1cc2c(c(C(=O)N3CCN(c4ncccn4)CC3)c1)OCCO2 | C1COCCO1.CCN(CC)CC.N.NS(=O)(=O)c1cc2c(c(C(=O)O)c1)OCCO2.O.c1cnc(N2CCNCC2)nc1>>NS(=O)(=O)c1cc2c(c(C(=O)N3CCN(c4ncccn4)CC3)c1)OCCO2 | US04186135_grants | 7ed0c8e2fa36fac7df8b80d714dd3ee9c90bf158afbe8d05651c069b | C1COCCO1.CCN(CC)CC.N.O.O[C:10]([c:9]1[c:8]2[c:7]([cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:24]1)[O:28][CH2:27][CH2:26][O:25]2)=[O:11].[NH:12]1[CH2:13][CH2:14][N:15]([c:16]2[n:17][cH:18][cH:19][cH:20][n:21]2)[CH2:22][CH2:23]1 | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][c:7]2[c:8]([c:9]([C:10](=[O:11])[N:12]3[CH2:13][CH2:14][N:15]([c:16]4[n:17][cH:18][cH:19][cH:20][n:21]4)[CH2:22][CH2:23]3)[cH:24]1)[O:25][CH2:26][CH2:27][O:28]2 | ([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 | C1COCCO1.CCN(CC)CC.N.O | 44 |