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
|
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
223,285 | 749,239 | 1,233,550 | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][C:16]2([CH3:23])[CH3:22])=[CH:10][N:9]=1)(C)(C)C.Cl>O1CCOCC1.CO>[CH3:22][C:16]1([CH3:23])[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][N:15]1[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1 | null | US08273882B2_0625 | 2,012 | C1COCCO1.CC(C)(C)OC(=O)[NH:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17][C:14]2([CH3:15])[CH3:16])[cH:13][n:12]1.CO.Cl>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]2)[C:14]([CH3:15])([CH3:16])[CH2:17]1 | 0.712074 | C1COCCO1.CN1CCN(Cc2ccc(NC(=O)OC(C)(C)C)nc2)C(C)(C)C1.CO.Cl>>CN1CCN(Cc2ccc(N)nc2)C(C)(C)C1 | C1COCCO1.CN1CCN(Cc2ccc(NC(=O)OC(C)(C)C)nc2)C(C)(C)C1.CO.Cl>>CN1CCN(Cc2ccc(N)nc2)C(C)(C)C1 | US08273882B2_0625grants | cd98e15507568b7a36409efb918f0396d13461b1f5f81a24502b90bd | C1COCCO1.CC(C)(C)OC(=O)[NH:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:17][C:14]2([CH3:15])[CH3:16])[cH:13][n:12]1.CO.Cl | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]2)[C:14]([CH3:15])([CH3:16])[CH2:17]1 | ([#7;a:3]:[c:2]-[NH2;D1;+0:1])>>(C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]:[#7;a:3]) | 6905d248c6bbf73da0f49e65e74cc1808102d866c8a59a2c8c619681 | 1 | 1 | C1COCCO1.CO.Cl | 885 |
142,638 | 513,811 | 861,130 | [NH2:1][CH2:2][CH2:3][OH:4].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH:15]=O>>[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][NH:1][CH2:2][CH2:3][OH:4] | null | US07435815B2_0277 | 2,008 | O=[CH:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1.[OH:1][CH2:2][CH2:3][NH2:4]>>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1 | 0.991862 | NCCO.O=Cc1ccc2ccccc2n1>>OCCNCc1ccc2ccccc2n1 | NCCO.O=Cc1ccc2ccccc2n1>>OCCNCc1ccc2ccccc2n1 | US07435815B2_0277grants | 989ed4d6fe1e492db8a18976ed1d9981d871b8c661bd2fb56a1e8f7c | O=[CH:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1.[OH:1][CH2:2][CH2:3][NH2:4] | [OH:1][CH2:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1 | ([#7;a:3]:[c:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C:4])>>(O=[CH;D2;+0:1]-[c:2]:[#7;a:3]).([C:4]-[NH2;D1;+0:5]) | 9ec116ea9d524dc10e4944fdcca64b025ecd1e9172f4c5794983c2b5 | 1 | 1 | null | 775 |
275,278 | 903,114 | 1,505,649 | [CH:1]1([NH:4][CH:5]2[CH2:10][CH2:9][N:8]([C:11]3[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[N:29]1[C:33]([CH3:34])=[N:32][CH:31]=[N:30]1)[C:23](O)=[O:24]>>[CH:1]1([N:4]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]3[N:12]=[CH:13][C:14]([CH2:17][CH3:18])=[CH:15][N:16]=3)[CH2:7][CH2:6]2)[C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([N:29]3[C:33]([CH3:34])=[N:32][CH:31]=[N:30]3)=[C:20]([F:19])[CH:21]=2)[CH2:2][CH2:3]1 | null | US08822471B2_0660 | 2,014 | O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17](-[n:18]2[n:19][cH:20][n:21][c:22]2[CH3:23])[c:24]([F:25])[cH:26]1.[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([NH:11][CH:27]3[CH2:28][CH2:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([N:11]([C:12](=[O:13])[c:14]3[cH:15][cH:16][c:17](-[n:18]4[n:19][cH:20][n:21][c:22]4[CH3:23])[c:24]([F:25])[cH:26]3)[CH:27]3[CH2:28][CH2:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]1 | 0.803487 | CCc1cnc(N2CCC(NC3CC3)CC2)nc1.Cc1ncnn1-c1ccc(C(=O)O)cc1F>>CCc1cnc(N2CCC(N(C(=O)c3ccc(-n4ncnc4C)c(F)c3)C3CC3)CC2)nc1 | CCc1cnc(N2CCC(NC3CC3)CC2)nc1.Cc1ncnn1-c1ccc(C(=O)O)cc1F>>CCc1cnc(N2CCC(N(C(=O)c3ccc(-n4ncnc4C)c(F)c3)C3CC3)CC2)nc1 | US08822471B2_0660grants | f3bd0e831e937be2adb75f96fa8e068ca51a4ad99469d7e7c9f4978c | O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17](-[n:18]2[n:19][cH:20][n:21][c:22]2[CH3:23])[c:24]([F:25])[cH:26]1.[CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([NH:11][CH:27]3[CH2:28][CH2:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]1 | [CH3:1][CH2:2][c:3]1[cH:4][n:5][c:6]([N:7]2[CH2:8][CH2:9][CH:10]([N:11]([C:12](=[O:13])[c:14]3[cH:15][cH:16][c:17](-[n:18]4[n:19][cH:20][n:21][c:22]4[CH3:23])[c:24]([F:25])[cH:26]3)[CH:27]3[CH2:28][CH2:29]3)[CH2:30][CH2:31]2)[n:32][cH:33]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 | null | 44 |
435,649 | 1,878,185 | null | [N:1]1[CH:6]=[CH:5][C:4]([O:7][C@@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]([CH2:20][CH3:21])[C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.O.CO.[OH-].[Li+]>C1COCC1>[N:1]1[CH:2]=[CH:3][C:4]([O:7][C@@H:8]2[CH2:9][CH2:10][C@H:11]([CH:14]([CH2:20][CH3:21])[C:15]([OH:17])=[O:16])[CH2:12][CH2:13]2)=[CH:5][CH:6]=1 | |f:3.4| | US20160137653A1_0484 | 2,016 | C1CCOC1.CC[O:6][C:4]([CH:3]([CH2:2][CH3:1])[C@H:7]1[CH2:8][CH2:9][C@@H:10]([O:11][c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)=[O:5].CO.O.[Li+].[OH-]>>[CH3:1][CH2:2][CH:3]([C:4](=[O:5])[OH:6])[C@H:7]1[CH2:8][CH2:9][C@@H:10]([O:11][c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | 0.935907 | C1CCOC1.CCOC(=O)C(CC)[C@H]1CC[C@@H](Oc2ccncc2)CC1.CO.O.[Li+]~[OH-]>>CCC(C(=O)O)[C@H]1CC[C@@H](Oc2ccncc2)CC1 | C1CCOC1.CCOC(=O)C(CC)[C@H]1CC[C@@H](Oc2ccncc2)CC1.CO.O.[Li+].[OH-]>>CCC(C(=O)O)[C@H]1CC[C@@H](Oc2ccncc2)CC1 | US20160137653A1_0484apps | 289df057224bf328659abe7f7531ce51fbcc9c4ca852e0e0e3e9c4a0 | C1CCOC1.CC[O:6][C:4]([CH:3]([CH2:2][CH3:1])[C@H:7]1[CH2:8][CH2:9][C@@H:10]([O:11][c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)=[O:5].CO.O.[Li+].[OH-] | [CH3:1][CH2:2][CH:3]([C:4](=[O:5])[OH:6])[C@H:7]1[CH2:8][CH2:9][C@@H:10]([O:11][c:12]2[cH:13][cH:14][n:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | C1CCOC1.CO.O.[Li+].[OH-] | 7 |
416,781 | 1,728,559 | null | [C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([P:38]([CH3:41])([CH3:40])=[O:39])[CH:33]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:42][C:43]1[CH:51]=[C:50]2[C:46]([CH2:47][C:48](=[O:52])[NH:49]2)=[CH:45][CH:44]=1.Cl.CC(O)C>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:42][C:43]4[CH:51]=[C:50]5[C:46]([CH2:47][C:48](=[O:52])[NH:49]5)=[CH:45][CH:44]=4)[N:26]=3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([P:38]([CH3:41])([CH3:40])=[O:39])[CH:33]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2] | null | US20150210722A1_0385 | 2,015 | C1CCOC1.CC(C)O.Cl.Cl[c:21]1[n:20][cH:19][cH:18][c:17]([O:16][c:15]2[cH:14][cH:13][c:12]([NH:11][C:9]([NH:8][c:7]3[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:51][n:40]3-[c:41]3[cH:42][cH:43][cH:44][c:45]([P:46]([CH3:47])([CH3:48])=[O:49])[cH:50]3)=[O:10])[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)[n:33]1.[NH2:22][c:23]1[cH:24][cH:25][c:26]2[c:27]([cH:28]1)[NH:29][C:30](=[O:31])[CH2:32]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][n:20][c:21]([NH:22][c:23]4[cH:24][cH:25][c:26]5[c:27]([cH:28]4)[NH:29][C:30](=[O:31])[CH2:32]5)[n:33]3)[c:34]3[cH:35][cH:36][cH:37][cH:38][c:39]23)[n:40](-[c:41]2[cH:42][cH:43][cH:44][c:45]([P:46]([CH3:47])([CH3:48])=[O:49])[cH:50]2)[n:51]1 | 0.253694 | C1CCOC1.CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ccnc(Cl)n3)c3ccccc23)n(-c2cccc(P(C)(C)=O)c2)n1.CC(C)O.Cl.Nc1ccc2c(c1)NC(=O)C2>>CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ccnc(Nc4ccc5c(c4)NC(=O)C5)n3)c3ccccc23)n(-c2cccc(P(C)(C)=O)c2)n1 | C1CCOC1.CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ccnc(Cl)n3)c3ccccc23)n(-c2cccc(P(C)(C)=O)c2)n1.CC(C)O.Cl.Nc1ccc2c(c1)NC(=O)C2>>CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ccnc(Nc4ccc5c(c4)NC(=O)C5)n3)c3ccccc23)n(-c2cccc(P(C)(C)=O)c2)n1 | US20150210722A1_0385apps | cc5c7a18cae71a25c630b65f2b1057f7e30295cd7d9ebc1c27871d6e | C1CCOC1.CC(C)O.Cl.Cl[c:21]1[n:20][cH:19][cH:18][c:17]([O:16][c:15]2[cH:14][cH:13][c:12]([NH:11][C:9]([NH:8][c:7]3[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:51][n:40]3-[c:41]3[cH:42][cH:43][cH:44][c:45]([P:46]([CH3:47])([CH3:48])=[O:49])[cH:50]3)=[O:10])[c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)[n:33]1.[NH2:22][c:23]1[cH:24][cH:25][c:26]2[c:27]([cH:28]1)[NH:29][C:30](=[O:31])[CH2:32]2 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([NH:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][n:20][c:21]([NH:22][c:23]4[cH:24][cH:25][c:26]5[c:27]([cH:28]4)[NH:29][C:30](=[O:31])[CH2:32]5)[n:33]3)[c:34]3[cH:35][cH:36][cH:37][cH:38][c:39]23)[n:40](-[c:41]2[cH:42][cH:43][cH:44][c:45]([P:46]([CH3:47])([CH3:48])=[O:49])[cH:50]2)[n:51]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([NH2;D1;+0:4]-[c:5]) | c9384cff16d8f069182a19c69b5ea34c7f585d1701326a079e8522b5 | 1 | 1 | C1CCOC1.CC(C)O.Cl | 808 |
121,889 | 451,045 | 765,515 | Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:11]([O:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:22]=1)([CH3:14])([CH3:12])[CH3:13] | |f:2.3.4| | US07160887B1_0551 | 2,007 | CN(C)C=O.Cl[c:17]1[n:18][cH:19][cH:20][cH:21][c:22]1[N+:23](=[O:24])[O-:25].O.O=C([O-])[O-].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:26]1.[K+].[K+]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][c:17]2[n:18][cH:19][cH:20][cH:21][c:22]2[N+:23](=[O:24])[O-:25])[cH:26]1 | 0.464675 | CC(C)(C)OC(=O)NCCc1cccc(O)c1.CN(C)C=O.O.O=C([O-])[O-]~[K+]~[K+].O=[N+]([O-])c1cccnc1Cl>>CC(C)(C)OC(=O)NCCc1cccc(Oc2ncccc2[N+](=O)[O-])c1 | CC(C)(C)OC(=O)NCCc1cccc(O)c1.CN(C)C=O.O.O=C([O-])[O-].O=[N+]([O-])c1cccnc1Cl.[K+].[K+]>>CC(C)(C)OC(=O)NCCc1cccc(Oc2ncccc2[N+](=O)[O-])c1 | US07160887B1_0551grants | 56e9b402c22d885d3df8b4df07a26e40199faf5e644503d284e7ae2d | CN(C)C=O.Cl[c:17]1[n:18][cH:19][cH:20][cH:21][c:22]1[N+:23](=[O:24])[O-:25].O.O=C([O-])[O-].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([OH:16])[cH:26]1.[K+].[K+] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][c:17]2[n:18][cH:19][cH:20][cH:21][c:22]2[N+:23](=[O:24])[O-:25])[cH:26]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:4]-[c:5])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([OH;D1;+0:4]-[c:5]) | b2089f895c9c3865a4c9e6f4846c2664b59c6ecfe2c6720268cccbc1 | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 516 |
99,799 | 384,231 | 657,024 | [OH:1][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]=2[CH:23]=O)[CH2:7][CH2:6]1)=[O:4].[CH2:25]([S:27]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34](=[O:39])[CH2:33]2)(=[O:29])=[O:28])[CH3:26]>>[CH2:25]([S:27]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34](=[O:39])/[C:33]/2=[CH:23]\[C:15]1[NH:16][C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=2[C:14]=1[CH2:13][CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][OH:1])[CH2:6][CH2:7]1)(=[O:28])=[O:29])[CH3:26] | null | US06777417B2_ | 2,004 | O=[CH:13][c:14]1[nH:15][c:16]2[c:17]([c:18]1[CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][OH:29])[CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34][CH2:35]2.[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:36](=[O:37])[NH:38]2>>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)/[C:12](=[CH:13]/[c:14]1[nH:15][c:16]3[c:17]([c:18]1[CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][OH:29])[CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:36](=[O:37])[NH:38]2 | 0.551501 | CCS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1[nH]c2c(c1CCCN1CCN(C(=O)CO)CC1)CCCC2>>CCS(=O)(=O)c1ccc2c(c1)/C(=C/c1[nH]c3c(c1CCCN1CCN(C(=O)CO)CC1)CCCC3)C(=O)N2 | CCS(=O)(=O)c1ccc2c(c1)CC(=O)N2.O=Cc1[nH]c2c(c1CCCN1CCN(C(=O)CO)CC1)CCCC2>>CCS(=O)(=O)c1ccc2c(c1)/C(=C/c1[nH]c3c(c1CCCN1CCN(C(=O)CO)CC1)CCCC3)C(=O)N2 | US06777417B2_grants | bb8ae308dea3c2615efc5bbf8afb541466a68b24bbc96d661f899ce5 | O=[CH:13][c:14]1[nH:15][c:16]2[c:17]([c:18]1[CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][OH:29])[CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34][CH2:35]2.[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:36](=[O:37])[NH:38]2 | [CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)/[C:12](=[CH:13]/[c:14]1[nH:15][c:16]3[c:17]([c:18]1[CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][OH:29])[CH2:30][CH2:31]1)[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:36](=[O:37])[NH:38]2 | ([#7:4]-[C:5](=[O;D1;H0:6])/[C;H0;D3;+0:7](-[c:8])=[CH;D2;+0:1]\[c:2]:[#7;a:3])>>(O=[CH;D2;+0:1]-[c:2]:[#7;a:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8]) | d7302f1d6a8331e9093c362eeb57d62731e1c3d285efc27b5eea9ca3 | 1 | 1 | null | 911 |
208,792 | 706,572 | 1,164,433 | [O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1.II>C(OCC)(=O)C>[C:9]([O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][O:1]1)(=[O:11])[CH3:10] | null | US08133880B2_0555 | 2,012 | CC(=O)O[C:2]([CH3:1])=[O:3].CCOC(C)=O.II.[OH:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]=[CH:10][O:11]1.c1ccncc1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]=[CH:10][O:11]1 | 0.527568 | CC(=O)OC(C)=O.CCOC(C)=O.II.OCC1CCC=CO1.c1ccncc1>>CC(=O)OCC1CCC=CO1 | CC(=O)OC(C)=O.CCOC(C)=O.II.OCC1CCC=CO1.c1ccncc1>>CC(=O)OCC1CCC=CO1 | US08133880B2_0555grants | 01cd1b813e8e5ced94cf1ad267a92fd5ad3c4406178e464fbe5e49dd | CC(=O)O[C:2]([CH3:1])=[O:3].CCOC(C)=O.II.[OH:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]=[CH:10][O:11]1.c1ccncc1 | [CH3:1][C:2](=[O:3])[O:4][CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]=[CH:10][O:11]1 | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | fa0bb6d907bde4c9e3e81661aedea03d23c0173afd7eccce9c8dc79b | 1 | 1 | CCOC(C)=O.II.c1ccncc1 | 254 |
296,192 | 964,440 | 1,622,482 | CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][C:27]=1[CH3:35].Cl.[C:37]([O:41][C:42](=[O:46])[CH2:43][CH2:44][NH2:45])([CH3:40])([CH3:39])[CH3:38]>CN(C=O)C>[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:45][CH2:44][CH2:43][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:46])=[O:32])=[CH:28][C:27]=1[CH3:35] | |f:0.1,3.4| | US09045389B2_0206 | 2,015 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:5]([c:4]1[cH:3][c:2]([CH3:1])[c:19]([Br:20])[cH:18][cH:17]1)=[O:6].[NH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18][c:19]1[Br:20] | 0.439065 | CC(C)(C)OC(=O)CCN~Cl.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.Cc1cc(C(=O)O)ccc1Br>>Cc1cc(C(=O)NCCC(=O)OC(C)(C)C)ccc1Br | CC(C)(C)OC(=O)CCN.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cc1cc(C(=O)O)ccc1Br.Cl.F[P-](F)(F)(F)(F)F>>Cc1cc(C(=O)NCCC(=O)OC(C)(C)C)ccc1Br | US09045389B2_0206grants | 9bca1026921159cf0db02397ff86e858dbe6e3aa043ff3cbf45a90e8 | CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cl.F[P-](F)(F)(F)(F)F.O[C:5]([c:4]1[cH:3][c:2]([CH3:1])[c:19]([Br:20])[cH:18][cH:17]1)=[O:6].[NH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | [CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18][c:19]1[Br:20] | ([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 |
318,989 | 1,036,919 | 1,757,702 | CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Br.[O:26]=[C:27]1[C:36]2[CH2:35][CH2:34][NH:33][CH2:32][C:31]=2[NH:30][C:29]2[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([O:43][CH3:44])=[O:42])[C:28]1=2.[CH3:45][C:46]1([C:49](O)=[O:50])[CH2:48][CH2:47]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:45][C:46]1([C:49]([N:33]2[CH2:32][C:31]3[NH:30][C:29]4[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([O:43][CH3:44])=[O:42])[C:28]=4[C:27](=[O:26])[C:36]=3[CH2:35][CH2:34]2)=[O:50])[CH2:48][CH2:47]1 | |f:0.1,2.3| | US09328111B2_0328 | 2,016 | Br.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:19](=[O:20])[C:21]1([CH3:22])[CH2:23][CH2:24]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]3[c:12]([c:13](=[O:14])[c:15]12)[CH2:16][CH2:17][NH:18][CH2:25]3>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]3[c:12]([c:13](=[O:14])[c:15]12)[CH2:16][CH2:17][N:18]([C:19](=[O:20])[C:21]1([CH3:22])[CH2:23][CH2:24]1)[CH2:25]3 | 0.693244 | Br~COC(=O)c1cccc2[nH]c3c(c(=O)c12)CCNC3.CC1(C(=O)O)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)c1cccc2[nH]c3c(c(=O)c12)CCN(C(=O)C1(C)CC1)C3 | Br.CC1(C(=O)O)CC1.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.COC(=O)c1cccc2[nH]c3c(c(=O)c12)CCNC3.F[P-](F)(F)(F)(F)F>>COC(=O)c1cccc2[nH]c3c(c(=O)c12)CCN(C(=O)C1(C)CC1)C3 | US09328111B2_0328grants | 656a89272c38192668152e5e0bf9659453fed22a337f26a8fdd42180 | Br.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:19](=[O:20])[C:21]1([CH3:22])[CH2:23][CH2:24]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]3[c:12]([c:13](=[O:14])[c:15]12)[CH2:16][CH2:17][NH:18][CH2:25]3 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[nH:10][c:11]3[c:12]([c:13](=[O:14])[c:15]12)[CH2:16][CH2:17][N:18]([C:19](=[O:20])[C:21]1([CH3:22])[CH2:23][CH2:24]1)[CH2:25]3 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | Br.CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F | 146 |
444,256 | 1,934,163 | null | C(OC([N:8]1[CH2:12][CH2:11][C:10]2([CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][C:34]5[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=5)=[CH:29][CH:28]=4)=[C:21]([C:23](=[O:25])[NH2:24])[CH:22]=3)[CH2:13]2)[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[CH2:13]1[C:10]2([CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:16][CH2:15][N:14]1[C:17]1[CH:18]=[N:19][C:20]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)=[CH:31][CH:32]=2)=[C:21]([CH:22]=1)[C:23]([NH2:24])=[O:25] | null | US20160264548A1_0860 | 2,016 | C1COCCO1.CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][C:10]2([CH2:9][CH2:8][N:7]([c:6]3[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:18]([O:19][c:20]4[cH:21][cH:22][c:23]([O:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[cH:32][cH:33]4)[n:17][cH:16]3)[CH2:15]2)[CH2:14]1.Cl.ClCCl>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][C:10]3([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:15]2)[cH:16][n:17][c:18]1[O:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]2)[cH:32][cH:33]1 | 0.948887 | C1COCCO1.CC(C)(C)OC(=O)N1CCC2(CCN(c3cnc(Oc4ccc(Oc5cccc(F)c5)cc4)c(C(N)=O)c3)C2)C1.Cl.ClCCl>>NC(=O)c1cc(N2CCC3(CCNC3)C2)cnc1Oc1ccc(Oc2cccc(F)c2)cc1 | C1COCCO1.CC(C)(C)OC(=O)N1CCC2(CCN(c3cnc(Oc4ccc(Oc5cccc(F)c5)cc4)c(C(N)=O)c3)C2)C1.Cl.ClCCl>>NC(=O)c1cc(N2CCC3(CCNC3)C2)cnc1Oc1ccc(Oc2cccc(F)c2)cc1 | US20160264548A1_0860apps | c14fba547d11d98801397a5347f46911320fa0587459ade03b140662 | C1COCCO1.CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][C:10]2([CH2:9][CH2:8][N:7]([c:6]3[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:18]([O:19][c:20]4[cH:21][cH:22][c:23]([O:24][c:25]5[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]5)[cH:32][cH:33]4)[n:17][cH:16]3)[CH2:15]2)[CH2:14]1.Cl.ClCCl | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([N:7]2[CH2:8][CH2:9][C:10]3([CH2:11][CH2:12][NH:13][CH2:14]3)[CH2:15]2)[cH:16][n:17][c:18]1[O:19][c:20]1[cH:21][cH:22][c:23]([O:24][c:25]2[cH:26][cH:27][cH:28][c:29]([F:30])[cH:31]2)[cH:32][cH:33]1 | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | C1COCCO1.Cl.ClCCl | 575 |
399,342 | 1,354,038 | null | Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([NH2:10])[N:3]=1.C(O)(=O)C.[O:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1.C(=O)([O-])O.[Na+].O>C(O)CCC>[Cl:9][C:6]1[N:5]=[C:4]([NH2:10])[N:3]=[C:2]([NH:21][CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)[C:7]=1[NH2:8] | |f:1.2,3.4| | US20130089512A1_1440 | 2,013 | CC(=O)O.CCCCO.Cl[c:8]1[c:6]([NH2:7])[c:4]([Cl:5])[n:3][c:2]([NH2:1])[n:16]1.O.O=C([O-])O.[NH2:9][CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.[Na+]>>[NH2:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([NH:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]1 | 0.765331 | CC(=O)O~NC1CCOCC1.CCCCO.Nc1nc(Cl)c(N)c(Cl)n1.O.O=C([O-])O~[Na+]>>Nc1nc(Cl)c(N)c(NC2CCOCC2)n1 | CC(=O)O.CCCCO.NC1CCOCC1.Nc1nc(Cl)c(N)c(Cl)n1.O.O=C([O-])O.[Na+]>>Nc1nc(Cl)c(N)c(NC2CCOCC2)n1 | US20130089512A1_1440apps | 873a8828d00413df078106d29111e5ee2d638b6eae5c7c609850ba80 | CC(=O)O.CCCCO.Cl[c:8]1[c:6]([NH2:7])[c:4]([Cl:5])[n:3][c:2]([NH2:1])[n:16]1.O.O=C([O-])O.[NH2:9][CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.[Na+] | [NH2:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([NH:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]1 | ([C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C:7]-[NH2;D1;+0:8]) | 9ba15a7b9393a64a7fde93acd4e7b07a21f5e92fd01af7815d1917a2 | 1 | 1 | CC(=O)O.CCCCO.O.O=C([O-])O.[Na+] | 166 |
198,368 | 678,725 | 1,120,374 | Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[CH:11][N:10]=1.[Cu][C:16]#[N:17]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[N:17])=[C:3]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][N:10]=2)[CH:4]=1 | null | US08039458B2_0420 | 2,011 | Br[c:13]1[c:7](-[c:6]2[n:2]([CH3:1])[n:3][cH:4][n:5]2)[cH:8][c:9]([F:10])[cH:11][cH:12]1.CN(C)C=O.[Cu][C:14]#[N:15]>>[CH3:1][n:2]1[n:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[C:14]#[N:15] | 0.988302 | CN(C)C=O.Cn1ncnc1-c1cc(F)ccc1Br.N#C[Cu]>>Cn1ncnc1-c1cc(F)ccc1C#N | CN(C)C=O.Cn1ncnc1-c1cc(F)ccc1Br.N#C[Cu]>>Cn1ncnc1-c1cc(F)ccc1C#N | US08039458B2_0420grants | f5f777696734a30a9b68d39ea6914254dcab673f798d6f0008b059e7 | Br[c:13]1[c:7](-[c:6]2[n:2]([CH3:1])[n:3][cH:4][n:5]2)[cH:8][c:9]([F:10])[cH:11][cH:12]1.CN(C)C=O.[Cu][C:14]#[N:15] | [CH3:1][n:2]1[n:3][cH:4][n:5][c:6]1-[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[C:14]#[N:15] | ([N;D1;H0:5]#[C;H0;D2;+0:4]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([Cu]-[C;H0;D2;+0:4]#[N;D1;H0:5]) | 53a16827b236bed654c73091aed173296d6d7451549d2385a03aeea2 | 1 | 1 | CN(C)C=O | 531 |
425,526 | 1,808,479 | null | Cl.[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C:17]([NH2:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:10])(=[O:9])[N:8]=1.[N:21]1([C:30]2[CH:31]=[C:32]([CH:36]=[CH:37][N:38]=2)[C:33](O)=[O:34])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[CH:22]1>>[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C:17]([NH:20][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][N:38]=[C:30]([N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[N:23]=[CH:22]4)[CH:31]=3)([CH3:18])[CH3:19])=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:10])(=[O:9])[N:8]=1 | |f:0.1| | US20150376176A1_0202 | 2,015 | Cl.O[C:20](=[O:21])[c:22]1[cH:23][cH:24][n:25][c:26](-[n:27]2[cH:28][n:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[cH:36]1.[CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12]([NH2:13])=[N:14][S:15](=[O:16])(=[O:17])[NH:18]2)[NH2:19]>>[CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12]([NH2:13])=[N:14][S:15](=[O:16])(=[O:17])[NH:18]2)[NH:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][n:25][c:26](-[n:27]2[cH:28][n:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[cH:36]1 | 0.447272 | CC(C)(N)COc1cccc2c1C(N)=NS(=O)(=O)N2~Cl.O=C(O)c1ccnc(-n2cnc3ccccc32)c1>>CC(C)(COc1cccc2c1C(N)=NS(=O)(=O)N2)NC(=O)c1ccnc(-n2cnc3ccccc32)c1 | CC(C)(N)COc1cccc2c1C(N)=NS(=O)(=O)N2.Cl.O=C(O)c1ccnc(-n2cnc3ccccc32)c1>>CC(C)(COc1cccc2c1C(N)=NS(=O)(=O)N2)NC(=O)c1ccnc(-n2cnc3ccccc32)c1 | US20150376176A1_0202apps | 66c4800bb50f103bef10f30ba815f3ecb0e8313d4829ff1bda7ffa5f | Cl.O[C:20](=[O:21])[c:22]1[cH:23][cH:24][n:25][c:26](-[n:27]2[cH:28][n:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[cH:36]1.[CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12]([NH2:13])=[N:14][S:15](=[O:16])(=[O:17])[NH:18]2)[NH2:19] | [CH3:1][C:2]([CH3:3])([CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[C:12]([NH2:13])=[N:14][S:15](=[O:16])(=[O:17])[NH:18]2)[NH:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][n:25][c:26](-[n:27]2[cH:28][n:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[cH:36]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 | Cl | 334 |
274,449 | 900,143 | 1,501,538 | [Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([F:11])=[CH:4][N:3]=1.Cl[Sn]Cl>CCO.Cl>[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:11])=[CH:4][N:3]=1 | null | US08815877B2_0230 | 2,014 | CCO.Cl.Cl[Sn]Cl.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][n:7][c:8]1[Br:9]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][n:7][c:8]1[Br:9] | 0.999322 | CCO.Cl.Cl[Sn]Cl.O=[N+]([O-])c1cc(F)cnc1Br>>Nc1cc(F)cnc1Br | CCO.Cl.Cl[Sn]Cl.O=[N+]([O-])c1cc(F)cnc1Br>>Nc1cc(F)cnc1Br | US08815877B2_0230grants | feae1863f1bedf4a306f1f1422c5bc4da9d6fbc42a27236a24b98d64 | CCO.Cl.Cl[Sn]Cl.O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[cH:6][n:7][c:8]1[Br:9] | [NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][n:7][c:8]1[Br:9] | ([#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 | CCO.Cl.Cl[Sn]Cl | 269 |
111,259 | 418,426 | 713,116 | [CH3:1][C:2]1([CH3:27])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[C:5]2[C:19]([CH3:26])=[C:20]([OH:25])[C:21]([CH3:24])=[C:22]([CH3:23])[C:4]=2[O:3]1.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1>>[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:25][C:20]2[C:21]([CH3:24])=[C:22]([CH3:23])[C:4]3[O:3][C:2]([CH3:27])([CH3:1])[CH:6]([C:7]4[CH:8]=[CH:9][C:10]([N:13]5[CH2:14][CH2:15][O:16][CH2:17][CH2:18]5)=[CH:11][CH:12]=4)[C:5]=3[C:19]=2[CH3:26])=[CH:32][CH:31]=1 | null | US07008950B1_0408 | 2,006 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]1.[OH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][cH:30]1)[C:31]([CH3:32])([CH3:33])[O:34]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[c:10]([CH3:11])[c:12]([CH3:13])[c:14]3[c:15]([c:16]2[CH3:17])[CH:18]([c:19]2[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[cH:29][cH:30]2)[C:31]([CH3:32])([CH3:33])[O:34]3)[cH:35][cH:36]1 | 0.564599 | COc1ccc(CCl)cc1.Cc1c(C)c2c(c(C)c1O)C(c1ccc(N3CCOCC3)cc1)C(C)(C)O2>>COc1ccc(COc2c(C)c(C)c3c(c2C)C(c2ccc(N4CCOCC4)cc2)C(C)(C)O3)cc1 | COc1ccc(CCl)cc1.Cc1c(C)c2c(c(C)c1O)C(c1ccc(N3CCOCC3)cc1)C(C)(C)O2>>COc1ccc(COc2c(C)c(C)c3c(c2C)C(c2ccc(N4CCOCC4)cc2)C(C)(C)O3)cc1 | US07008950B1_0408grants | 29280dce2b3ffc54638cc3bdec7c1213df795988dfbdc4fac879ab82 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]1.[OH:8][c:9]1[c:10]([CH3:11])[c:12]([CH3:13])[c:14]2[c:15]([c:16]1[CH3:17])[CH:18]([c:19]1[cH:20][cH:21][c:22]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][cH:30]1)[C:31]([CH3:32])([CH3:33])[O:34]2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[c:10]([CH3:11])[c:12]([CH3:13])[c:14]3[c:15]([c:16]2[CH3:17])[CH:18]([c:19]2[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[cH:29][cH:30]2)[C:31]([CH3:32])([CH3:33])[O:34]3)[cH:35][cH:36]1 | ([c:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Cl-[CH2;D2;+0:1]-[c:2]).([OH;D1;+0:3]-[c:4]) | 19ecb0c449632e1a0d99fd6d4c00076fad1615ed07bc86df1499acb5 | 1 | 1 | null | 49 |
9,146 | 46,686 | 75,379 | [NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[CH:11]([O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[O:16])([CH3:13])[CH3:12]>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:27]([NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:15]([O:14][CH:11]([CH3:13])[CH3:12])=[O:16])(=[O:25])=[O:24])=[O:28])[N:7]=1 | null | US04238621_ | 1,980 | ClCCl.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27].[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27])[n:28]1 | 0.438933 | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1.ClCCl>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | CC(C)OC(=O)c1ccccc1S(=O)(=O)N=C=O.COc1nc(C)nc(N)n1.ClCCl>>COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC(C)C)n1 | US04238621_grants | e6ebccbcb5d06dd555b296de74599619132646e6ffad9f8483e76f13 | ClCCl.[C:10](=[O:11])=[N:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27].[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH2:9])[n:28]1 | [CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([NH:9][C:10](=[O:11])[NH:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[O:24][CH:25]([CH3:26])[CH3:27])[n:28]1 | ([#7;a:1]:[c:2](:[#7;a:3])-[NH;D2;+0:4]-[C;H0;D3;+0:6](=[O;D1;H0:5])-[NH;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])>>([#7;a:1]:[c:2](:[#7;a:3])-[NH2;D1;+0:4]).([O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11]) | a18bc1b7c994fb20476ce65f3895524426072709624dfefe3ec991eb | 1 | 1 | ClCCl | 566 |
172,091 | 602,896 | 999,070 | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[I:12]Cl>C(Cl)Cl>[I:12][C:7]1[CH:6]=[CH:5][C:4]([NH2:9])=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:8]=1 | null | US07763657B2_0519 | 2,010 | ClCCl.Cl[I:6].[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:7][c:8]1[C:9]([F:10])([F:11])[F:12]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([I:6])[cH:7][c:8]1[C:9]([F:10])([F:11])[F:12] | 0.327231 | ClCCl.ClI.Nc1ccccc1C(F)(F)F>>Nc1ccc(I)cc1C(F)(F)F | ClCCl.ClI.Nc1ccccc1C(F)(F)F>>Nc1ccc(I)cc1C(F)(F)F | US07763657B2_0519grants | 4081cce9b6507aceca68f4ad95e56d442a19d3a1a44c89faf6e05ef6 | ClCCl.Cl[I:6].[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:7][c:8]1[C:9]([F:10])([F:11])[F:12] | [NH2:1][c:2]1[cH:3][cH:4][c:5]([I:6])[cH:7][c:8]1[C:9]([F:10])([F:11])[F:12] | ([I;H0;D1;+0:1]-[c;H0;D3;+0:3](:[c:2]):[c:4])>>(Cl-[I;H0;D1;+0:1]).([c:2]:[cH;D2;+0:3]:[c:4]) | 5f145faf5713f662105c26da53b5a30a3e5bab54eceeaed5e19cfa50 | 1 | 1 | ClCCl | 466 |
210,531 | 711,797 | 1,172,813 | O.NN.[CH3:4][C:5]1([CH3:20])[CH2:11][CH2:10][C:9](=[O:12])[NH:8][C:7]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:6]1=2>[Pd].C(O)C>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][CH2:11][C:5]([CH3:20])([CH3:4])[C:6]=2[CH:16]=1 | |f:0.1| | US08148391B2_3326 | 2,012 | CCO.NN.O.O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]2[c:15]([cH:14]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[NH:8]2.[Pd]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]21 | 0.898492 | CC1(C)CCC(=O)Nc2ccc([N+](=O)[O-])cc21.CCO.NN~O.[Pd]>>CC1(C)CCC(=O)Nc2ccc(N)cc21 | CC1(C)CCC(=O)Nc2ccc([N+](=O)[O-])cc21.CCO.NN.O.[Pd]>>CC1(C)CCC(=O)Nc2ccc(N)cc21 | US08148391B2_3326grants | 5576780696cc65d9687d15f1efb5dcc9e4551f429c3fd3ca34a88bee | CCO.NN.O.O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]2[c:15]([cH:14]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[NH:8]2.[Pd] | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]21 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.NN.O.[Pd] | 1 |
187,630 | 647,679 | 1,071,238 | [CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:14][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1 | |f:1.2.3.4.5.6,8.9| | US07932272B2_0574 | 2,011 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1.[Na+].[OH-]>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | 0.905639 | C1CCOC1.N#Cc1ccc(NCc2ccccc2)cc1.O.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+].[Na+]~[OH-]>>NCc1ccc(NCc2ccccc2)cc1 | C1CCOC1.N#Cc1ccc(NCc2ccccc2)cc1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-]>>NCc1ccc(NCc2ccccc2)cc1 | US07932272B2_0574grants | 75a864438e8f6d52038323ce5de0700cfa79864c502123933ad9ab86 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1.[Na+].[OH-] | [NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | ([NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>([N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]) | 35e65afef8055e95e791906e7b199974efd87c632e3445dab6183229 | 1 | 1 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-] | 175 |
277,579 | 910,057 | 1,520,104 | C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[C:11]2[C:16](=[N:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:12]2)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:23][O:22][C:20]([CH:13]1[C:14](=[O:19])[NH:15][C:16]2[N:17]=[CH:18][C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])=[CH:10][C:11]=2[CH2:12]1)=[O:21] | null | US08846711B2_0560 | 2,014 | CC(C)(C)[O:14][C:12](/[CH:11]=[CH:10]/[c:9]1[cH:8][c:7]2[c:17]([n:16][cH:15]1)[NH:18][C:19](=[O:20])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)=[O:13].ClCCl.O=C(O)C(F)(F)F>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])[OH:14])[cH:15][n:16][c:17]2[NH:18][C:19]1=[O:20] | 0.97568 | COC(=O)C1Cc2cc(/C=C/C(=O)OC(C)(C)C)cnc2NC1=O.ClCCl.O=C(O)C(F)(F)F>>COC(=O)C1Cc2cc(/C=C/C(=O)O)cnc2NC1=O | COC(=O)C1Cc2cc(/C=C/C(=O)OC(C)(C)C)cnc2NC1=O.ClCCl.O=C(O)C(F)(F)F>>COC(=O)C1Cc2cc(/C=C/C(=O)O)cnc2NC1=O | US08846711B2_0560grants | a2a1dab3a0e1bc8545f7e688ff38e91315aae96ac243a1bffdba2ac7 | CC(C)(C)[O:14][C:12](/[CH:11]=[CH:10]/[c:9]1[cH:8][c:7]2[c:17]([n:16][cH:15]1)[NH:18][C:19](=[O:20])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)=[O:13].ClCCl.O=C(O)C(F)(F)F | [CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][c:9](/[CH:10]=[CH:11]/[C:12](=[O:13])[OH:14])[cH:15][n:16][c:17]2[NH:18][C:19]1=[O:20] | ([C:5]=[C:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]) | 6ff98642fe169fc36a0c3087b8c8f8683de611764f3492c499fed3e6 | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 158 |
376,830 | 877,632 | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[N:10]([C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([N:24]3[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]3[C:30]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[Cl:37])[N:16]=2)[CH:11]=[C:12]([CH3:14])[N:13]=1.CO.O.NN>[Ni].O>[NH2:21][C:20]1[C:15]([N:10]2[CH:11]=[C:12]([CH3:14])[N:13]=[C:9]2[C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])=[N:16][C:17]([N:24]2[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]2[C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=2[Cl:37])=[CH:18][CH:19]=1 | |f:2.3| | US20100120762A1_0532 | 2,010 | CO.NN.O.O.O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5](-[n:4]2[cH:3][c:2]([CH3:1])[n:35][c:26]2-[c:27]2[cH:28][c:29]([Cl:30])[cH:31][cH:32][c:33]2[Cl:34])[n:25][c:10]1-[n:11]1[cH:12][c:13]([CH3:14])[n:15][c:16]1-[c:17]1[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]1[Cl:24].[Ni]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[c:10](-[n:11]3[cH:12][c:13]([CH3:14])[n:15][c:16]3-[c:17]3[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]3[Cl:24])[n:25]2)[c:26](-[c:27]2[cH:28][c:29]([Cl:30])[cH:31][cH:32][c:33]2[Cl:34])[n:35]1 | 0.890226 | CO.Cc1cn(-c2ccc([N+](=O)[O-])c(-n3cc(C)nc3-c3cc(Cl)ccc3Cl)n2)c(-c2cc(Cl)ccc2Cl)n1.NN~O.O.[Ni]>>Cc1cn(-c2ccc(N)c(-n3cc(C)nc3-c3cc(Cl)ccc3Cl)n2)c(-c2cc(Cl)ccc2Cl)n1 | CO.Cc1cn(-c2ccc([N+](=O)[O-])c(-n3cc(C)nc3-c3cc(Cl)ccc3Cl)n2)c(-c2cc(Cl)ccc2Cl)n1.NN.O.O.[Ni]>>Cc1cn(-c2ccc(N)c(-n3cc(C)nc3-c3cc(Cl)ccc3Cl)n2)c(-c2cc(Cl)ccc2Cl)n1 | US20100120762A1_0532apps | 1eded554cf3c26a4b3f61d47d8fe20d124df82bf40f1bd1db4a87626 | CO.NN.O.O.O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5](-[n:4]2[cH:3][c:2]([CH3:1])[n:35][c:26]2-[c:27]2[cH:28][c:29]([Cl:30])[cH:31][cH:32][c:33]2[Cl:34])[n:25][c:10]1-[n:11]1[cH:12][c:13]([CH3:14])[n:15][c:16]1-[c:17]1[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]1[Cl:24].[Ni] | [CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[c:10](-[n:11]3[cH:12][c:13]([CH3:14])[n:15][c:16]3-[c:17]3[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]3[Cl:24])[n:25]2)[c:26](-[c:27]2[cH:28][c:29]([Cl:30])[cH:31][cH:32][c:33]2[Cl:34])[n:35]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 | CO.NN.O.O.[Ni] | 269 |
145,680 | 522,577 | 875,642 | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])=[O:15])[C:12](=[O:23])[NH:11][C:10]([CH3:24])=[C:9]2[C:25]([O:27][CH3:28])=[O:26])=[CH:4][CH:3]=1.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([NH2:48])[CH:43]=2)[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].Cl.CN(C)CCCN=C=NCC.C(Cl)Cl>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:43]=[C:44]([CH:45]=[CH:46][CH:47]=2)[NH:48][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][NH:16][C:14]([N:13]2[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:9]([C:25]([O:27][CH3:28])=[O:26])=[C:10]([CH3:24])[NH:11][C:12]2=[O:23])=[O:15])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:30])[CH3:31] | |f:2.3| | US07473698B2_0288 | 2,009 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl.ClCCl.O.O[C:18]([CH2:17][CH2:16][CH2:15][NH:14][C:12]([N:11]1[C:9](=[O:10])[NH:8][C:6]([CH3:7])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:40]1[c:41]1[cH:42][cH:43][c:44]([F:45])[cH:46][cH:47]1)=[O:13])=[O:19].[NH2:20][c:21]1[cH:22][cH:23][cH:24][c:25]([CH:26]2[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]2)[cH:39]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9](=[O:10])[N:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][c:25]([CH:26]3[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]3)[cH:39]2)[CH:40]1[c:41]1[cH:42][cH:43][c:44]([F:45])[cH:46][cH:47]1 | 0.350825 | CC(C)(C)OC(=O)N1CCC(c2cccc(N)c2)CC1.CCN=C=NCCCN(C)C~Cl.CN(C)C=O.CN(C)c1ccncc1.COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)O)C1c1ccc(F)cc1.ClCCl.O>>COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)Nc2cccc(C3CCN(C(=O)OC(C)(C)C)CC3)c2)C1c1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCC(c2cccc(N)c2)CC1.CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)O)C1c1ccc(F)cc1.Cl.ClCCl.O>>COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)Nc2cccc(C3CCN(C(=O)OC(C)(C)C)CC3)c2)C1c1ccc(F)cc1 | US07473698B2_0288grants | 5d665a66fd89110853e8272e718724e2d6139a65cb50645ac1441725 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl.ClCCl.O.O[C:18]([CH2:17][CH2:16][CH2:15][NH:14][C:12]([N:11]1[C:9](=[O:10])[NH:8][C:6]([CH3:7])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:40]1[c:41]1[cH:42][cH:43][c:44]([F:45])[cH:46][cH:47]1)=[O:13])=[O:19].[NH2:20][c:21]1[cH:22][cH:23][cH:24][c:25]([CH:26]2[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]2)[cH:39]1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9](=[O:10])[N:11]([C:12](=[O:13])[NH:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][c:25]([CH:26]3[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]3)[cH:39]2)[CH:40]1[c:41]1[cH:42][cH:43][c:44]([F:45])[cH:46][cH:47]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 993a80a34f6acdc22e1630fbdadc440460d93877c75dd17e7db680f0 | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl.ClCCl.O | 365 |
185,464 | 641,861 | 1,061,609 | [Cl:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([Cl:49])[CH:48]=1)[CH2:5][N:6]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[C:35]1[CH:40]=[C:39]([CH:41]([CH3:43])[CH3:42])[CH:38]=[CH:37][C:36]=1[O:44][CH3:45])[C:7]1[N:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[CH:9][N:8]=1.Cl.O1CCOCC1>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([Cl:49])[CH:48]=1)[CH2:5][N:6]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[C:35]1[CH:40]=[C:39]([CH:41]([CH3:43])[CH3:42])[CH:38]=[CH:37][C:36]=1[O:44][CH3:45])[C:7]1[N:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][N:12]=1 | |f:1.2,3.4.5| | US07906517B2_0681 | 2,011 | C1COCCO1.CC(C)(C)[O:43][C:41]([CH2:40][CH2:39][CH2:38][O:37][c:36]1[cH:35][n:34][c:33]([N:23]([CH2:22][c:21]2[c:12](-[c:11]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10]3)[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]2)[CH2:24][c:25]2[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]2)[n:45][cH:44]1)=[O:42].Cl.O.[Cl-].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10][c:11]1-[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][c:21]1[CH2:22][N:23]([CH2:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]1)[c:33]1[n:34][cH:35][c:36]([O:37][CH2:38][CH2:39][CH2:40][C:41](=[O:42])[OH:43])[cH:44][n:45]1 | 0.167401 | C1COCCO1~Cl.COc1ccc(C(C)C)cc1-c1ccc(C(F)(F)F)cc1CN(Cc1cc(Cl)cc(Cl)c1)c1ncc(OCCCC(=O)OC(C)(C)C)cn1.O~[Cl-]~[Na+]>>COc1ccc(C(C)C)cc1-c1ccc(C(F)(F)F)cc1CN(Cc1cc(Cl)cc(Cl)c1)c1ncc(OCCCC(=O)O)cn1 | C1COCCO1.COc1ccc(C(C)C)cc1-c1ccc(C(F)(F)F)cc1CN(Cc1cc(Cl)cc(Cl)c1)c1ncc(OCCCC(=O)OC(C)(C)C)cn1.Cl.O.[Cl-].[Na+]>>COc1ccc(C(C)C)cc1-c1ccc(C(F)(F)F)cc1CN(Cc1cc(Cl)cc(Cl)c1)c1ncc(OCCCC(=O)O)cn1 | US07906517B2_0681grants | b698aea3b4ea1b294461f63a238ad422603c8d8af9b21bf819f8e77b | C1COCCO1.CC(C)(C)[O:43][C:41]([CH2:40][CH2:39][CH2:38][O:37][c:36]1[cH:35][n:34][c:33]([N:23]([CH2:22][c:21]2[c:12](-[c:11]3[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10]3)[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]2)[CH2:24][c:25]2[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]2)[n:45][cH:44]1)=[O:42].Cl.O.[Cl-].[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH3:8])[CH3:9])[cH:10][c:11]1-[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][c:21]1[CH2:22][N:23]([CH2:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]1)[c:33]1[n:34][cH:35][c:36]([O:37][CH2:38][CH2:39][CH2:40][C:41](=[O:42])[OH:43])[cH:44][n:45]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | cd4c8dfb74ae00d4ec8387e8837370d2f9fd4ad5e54ff56c9878f839 | 1 | 1 | C1COCCO1.Cl.O.[Cl-].[Na+] | 278 |
442,651 | 1,923,838 | null | [Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])OC2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[F:8].ClC1N=C(NC(N2CCN3N=CC(C4C=CC(F)=CC=4)=C3C2)=O)C=CC=1F.[F:46][C:47]1[CH:52]=[C:51]([F:53])[CH:50]=[CH:49][C:48]=1[C:54]1[N:55]=[N:56][N:57]2[CH2:62][CH2:61][NH:60][CH2:59][C:58]=12.FC1C=CC(C2C=NN3CCNCC=23)=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:60]2[CH2:61][CH2:62][N:57]3[N:56]=[N:55][C:54]([C:48]4[CH:49]=[CH:50][C:51]([F:53])=[CH:52][C:47]=4[F:46])=[C:58]3[CH2:59]2)=[O:18])[CH:5]=[CH:6][C:7]=1[F:8] | null | US20160237090A1_1322 | 2,016 | Fc1ccc(-c2cnn3c2CNCC3)cc1.O=C(Nc1ccc(F)c(Cl)n1)N1CCn2ncc(-c3ccc(F)cc3)c2C1.[NH:12]1[CH2:13][CH2:14][n:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]3[F:26])[c:27]2[CH2:28]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]2)cc1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1)[N:12]1[CH2:13][CH2:14][n:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]3[F:26])[c:27]2[CH2:28]1 | 0.5503 | Fc1ccc(-c2cnn3c2CNCC3)cc1.Fc1ccc(-c2nnn3c2CNCC3)c(F)c1.O=C(Nc1ccc(F)c(Cl)c1)Oc1ccccc1.O=C(Nc1ccc(F)c(Cl)n1)N1CCn2ncc(-c3ccc(F)cc3)c2C1>>O=C(Nc1ccc(F)c(Cl)c1)N1CCn2nnc(-c3ccc(F)cc3F)c2C1 | Fc1ccc(-c2cnn3c2CNCC3)cc1.Fc1ccc(-c2nnn3c2CNCC3)c(F)c1.O=C(Nc1ccc(F)c(Cl)c1)Oc1ccccc1.O=C(Nc1ccc(F)c(Cl)n1)N1CCn2ncc(-c3ccc(F)cc3)c2C1>>O=C(Nc1ccc(F)c(Cl)c1)N1CCn2nnc(-c3ccc(F)cc3F)c2C1 | US20160237090A1_1322apps | 5785feaf64adaa720b44ce520837b8de9dc21514e91c700865d40fc3 | Fc1ccc(-c2cnn3c2CNCC3)cc1.O=C(Nc1ccc(F)c(Cl)n1)N1CCn2ncc(-c3ccc(F)cc3)c2C1.[NH:12]1[CH2:13][CH2:14][n:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]3[F:26])[c:27]2[CH2:28]1.c1ccc(O[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]2)cc1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1)[N:12]1[CH2:13][CH2:14][n:15]2[n:16][n:17][c:18](-[c:19]3[cH:20][cH:21][c:22]([F:23])[cH:24][c:25]3[F:26])[c:27]2[CH2:28]1 | ([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-c1:c:c:c:c:c:1).([C:4]-[NH;D2;+0:5]-[C:6]) | 1f2ef2bcca895e8e6b88763a230093913f4071e08542f36b112a8e55 | 1 | 1 | Fc1ccc(-c2cnn3c2CNCC3)cc1.O=C(Nc1ccc(F)c(Cl)n1)N1CCn2ncc(-c3ccc(F)cc3)c2C1 | 525 |
6,561 | 33,984 | 52,133 | [CH2:1]([C:3](=[CH:6][CH2:7][CH2:8][CH3:9])[CH:4]=[O:5])[CH3:2].C(C(CCCC)C=O)C>CCCCCCC>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2] | null | US04138588_ | 1,979 | CCCC=C(C=O)CC.CCCCCCC.[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH:8]=[O:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][OH:9] | 0.904193 | CCCC=C(C=O)CC.CCCCC(C=O)CC.CCCCCCC>>CCCCC(CC)CO | CCCC=C(C=O)CC.CCCCC(C=O)CC.CCCCCCC>>CCCCC(CC)CO | US04138588_grants | 2e508534086423cdc87518997978a85779f46bb608debd435386f770 | CCCC=C(C=O)CC.CCCCCCC.[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH:8]=[O:9] | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][OH:9] | ([C:1]-[CH2;D2;+0:2]-[OH;D1;+0:3])>>([C:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3]) | 1dd4dec9f0a6b0036351341bbee3ca89ca2d60857539d67a1cf43010 | 1 | 1 | CCCC=C(C=O)CC.CCCCCCC | 223 |
127,163 | 467,222 | 791,348 | [Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:12].[C:13](Cl)(=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1 | null | US07230020B2_0543 | 2,007 | C1CCOC1.CCN(CC)CC.Cl[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]2[s:15][c:16]([CH3:17])[n:18][c:19]2[c:20]1[Cl:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]3[s:15][c:16]([CH3:17])[n:18][c:19]3[c:20]2[Cl:21])[cH:22]1 | 0.988274 | C1CCOC1.CCN(CC)CC.COc1cccc(C(=O)Cl)c1.Cc1nc2c(Cl)c(N)ccc2s1>>COc1cccc(C(=O)Nc2ccc3sc(C)nc3c2Cl)c1 | C1CCOC1.CCN(CC)CC.COc1cccc(C(=O)Cl)c1.Cc1nc2c(Cl)c(N)ccc2s1>>COc1cccc(C(=O)Nc2ccc3sc(C)nc3c2Cl)c1 | US07230020B2_0543grants | 5e298da9002f749364eb7be5640f6cfb9f8e937834c257fc32bad038 | C1CCOC1.CCN(CC)CC.Cl[C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]2[s:15][c:16]([CH3:17])[n:18][c:19]2[c:20]1[Cl:21] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]3[s:15][c:16]([CH3:17])[n:18][c:19]3[c:20]2[Cl:21])[cH:22]1 | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 81bbe9d480d200be1437e9ca625a57474abf80dfdc397cf8e383daca | 1 | 1 | C1CCOC1.CCN(CC)CC | 11 |
368,262 | 736,131 | null | [Se](=O)=[O:2].[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[CH:14]=1)[N:11]=[C:10]([CH3:28])[CH:9]=[CH:8]2>O1CCOCC1.C(Cl)Cl>[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([N:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:19][CH2:20]3)[CH:14]=1)[N:11]=[C:10]([CH:28]=[O:2])[CH:9]=[CH:8]2 | null | US20090181950A1_0190 | 2,009 | C1COCCO1.ClCCl.O=[Se]=[O:22].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:23][c:24]23)[CH2:25][CH2:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][c:17]3[cH:18][cH:19][c:20]([CH:21]=[O:22])[n:23][c:24]23)[CH2:25][CH2:26]1 | 0.22458 | C1COCCO1.Cc1ccc2cc(Br)cc(N3CCN(C(=O)OC(C)(C)C)CC3)c2n1.ClCCl.O=[Se]=O>>CC(C)(C)OC(=O)N1CCN(c2cc(Br)cc3ccc(C=O)nc23)CC1 | C1COCCO1.Cc1ccc2cc(Br)cc(N3CCN(C(=O)OC(C)(C)C)CC3)c2n1.ClCCl.O=[Se]=O>>CC(C)(C)OC(=O)N1CCN(c2cc(Br)cc3ccc(C=O)nc23)CC1 | US20090181950A1_0190apps | d40b1343a972be67346b3f9869828a925fe60ac034568ac06e4e4682 | C1COCCO1.ClCCl.O=[Se]=[O:22].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:23][c:24]23)[CH2:25][CH2:26]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][c:14]([Br:15])[cH:16][c:17]3[cH:18][cH:19][c:20]([CH:21]=[O:22])[n:23][c:24]23)[CH2:25][CH2:26]1 | ([#7;a:2]:[c:3]-[CH;D2;+0:4]=[O;H0;D1;+0:1])>>(O=[Se]=[O;H0;D1;+0:1]).([#7;a:2]:[c:3]-[CH3;D1;+0:4]) | f41aa73691bf801ae137e1b077d80b11af5db819c062508bec53095d | 1 | 1 | C1COCCO1.ClCCl | 619 |
123,893 | 457,015 | 774,233 | C([N:8]1[CH2:13][CH2:12][C:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:14][C:11]1([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1 | |f:3.4.5| | US07186731B2_0454 | 2,007 | CCOC(C)=O.CO.[OH-].[OH-].[Pd+2].c1ccc(C[N:13]2[CH2:12][CH2:11][C:2]([CH3:1])([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:15][CH2:14]2)cc1>>[CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | 0.415865 | CC1(NC(=O)OC(C)(C)C)CCN(Cc2ccccc2)CC1.CCOC(C)=O.CO.[OH-]~[OH-]~[Pd+2]>>CC1(NC(=O)OC(C)(C)C)CCNCC1 | CC1(NC(=O)OC(C)(C)C)CCN(Cc2ccccc2)CC1.CCOC(C)=O.CO.[OH-].[OH-].[Pd+2]>>CC1(NC(=O)OC(C)(C)C)CCNCC1 | US07186731B2_0454grants | 77f7673c8e67dfbebbfc7a9261044952b72ae8b45aba0ca3e2bea468 | CCOC(C)=O.CO.[OH-].[OH-].[Pd+2].c1ccc(C[N:13]2[CH2:12][CH2:11][C:2]([CH3:1])([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:15][CH2:14]2)cc1 | [CH3:1][C:2]1([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | ([C:1]-[NH;D2;+0:2]-[C:3])>>([C:1]-[N;H0;D3;+0:2](-[C:3])-C-c1:c:c:c:c:c:1) | f58207c6c64a5b48e40756ac3ba50fe69cdf9b1d18b6063ebd95ff15 | 0.5 | 2 | CCOC(C)=O.CO.[OH-].[OH-].[Pd+2] | 84 |
128,060 | 469,666 | 794,969 | [F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1 | |f:2.3| | US07238813B2_0594 | 2,007 | Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.[CH:9]1=[CH:10][CH2:11][CH2:12][CH2:13][O:14]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:15][c:16]1[F:17].c1cc[nH+]cc1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[cH:15][c:16]1[F:17] | 0.887149 | C1=COCCC1.Cc1ccc(S(=O)(=O)[O-])cc1~c1cc[nH+]cc1.ClCCl.O=[N+]([O-])c1ccc(O)cc1F>>O=[N+]([O-])c1ccc(OC2CCCCO2)cc1F | C1=COCCC1.Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.O=[N+]([O-])c1ccc(O)cc1F.c1cc[nH+]cc1>>O=[N+]([O-])c1ccc(OC2CCCCO2)cc1F | US07238813B2_0594grants | 590f76a88a5746d1eaae34be2ed0baf4dc421f926c2dde8f53c94649 | Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.[CH:9]1=[CH:10][CH2:11][CH2:12][CH2:13][O:14]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:15][c:16]1[F:17].c1cc[nH+]cc1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14]2)[cH:15][c:16]1[F:17] | ([#8:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[C:4])-[O;H0;D2;+0:5]-[c:6])>>([#8:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[C:4]).([OH;D1;+0:5]-[c:6]) | d563940aa788639c785444cf5408665f77a2de5dbdfeb988d65a3761 | 1 | 1 | Cc1ccc(S(=O)(=O)[O-])cc1.ClCCl.c1cc[nH+]cc1 | 319 |
14,953 | 74,111 | 121,934 | [CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:13]1[CH2:14][O:15][C:5]2([CH2:4][CH2:3][C:2]([CH3:1])([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6]2)[O:8]1 | |f:2.3| | US04461902_ | 1,984 | Cc1ccc(S(=O)(=O)O)cc1.O.O.O[CH2:13][CH2:14][OH:15].[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1.c1ccccc1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2 | 0.483507 | COC(=O)C1(C)CCC(=O)CC1.Cc1ccc(S(=O)(=O)O)cc1~O.O.OCCO.c1ccccc1>>COC(=O)C1(C)CCC2(CC1)OCCO2 | COC(=O)C1(C)CCC(=O)CC1.Cc1ccc(S(=O)(=O)O)cc1.O.O.OCCO.c1ccccc1>>COC(=O)C1(C)CCC2(CC1)OCCO2 | US04461902_grants | cf91bd711948fc079b4ec790eef3330870e78a80e17e6cdc112d433e | Cc1ccc(S(=O)(=O)O)cc1.O.O.O[CH2:13][CH2:14][OH:15].[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]1.c1ccccc1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1([CH3:6])[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2 | ([C:4]-[C;H0;D4;+0:5]1(-[C:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1)>>(O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3]).([C:4]-[C;H0;D3;+0:5](-[C:6])=[O;H0;D1;+0:7]) | e4a5e247248b212ffa5f297acaa21d528da5e85cae1a0e49a41decf5 | 1 | 1 | Cc1ccc(S(=O)(=O)O)cc1.O.O.c1ccccc1 | 265 |
339,599 | 290,986 | null | Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][CH:13]1[CH2:18][NH:17][CH2:16][CH2:15][NH:14]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:12][CH:13]1[NH:14][CH2:15][CH2:16][N:17]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)[CH2:18]1 | null | US20050234046A1_0323 | 2,005 | CCN(CC)CC.Cc1ccccc1.ClCCl.Cl[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]1.[CH3:1][CH:2]1[CH2:3][NH:4][CH2:15][CH2:16][NH:17]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]2)[CH2:15][CH2:16][NH:17]1 | 0.335781 | CC1CNCCN1.CCN(CC)CC.Cc1ccccc1.ClCCl.FC(F)(F)c1ccc(Cl)nc1>>CC1CN(c2ccc(C(F)(F)F)cn2)CCN1 | CC1CNCCN1.CCN(CC)CC.Cc1ccccc1.ClCCl.FC(F)(F)c1ccc(Cl)nc1>>CC1CN(c2ccc(C(F)(F)F)cn2)CCN1 | US20050234046A1_0323apps | afb6c1563a49009db7973f669fa6941691ae996ad746a6c1ac43a78e | CCN(CC)CC.Cc1ccccc1.ClCCl.Cl[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]1.[CH3:1][CH:2]1[CH2:3][NH:4][CH2:15][CH2:16][NH:17]1 | [CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][n:14]2)[CH2:15][CH2:16][NH:17]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | d775cf39c89817610201eb77d7f2c05750999ab6870ec4bcf35a0a78 | 1 | 1 | CCN(CC)CC.Cc1ccccc1.ClCCl | 220 |
303,506 | 986,774 | 1,664,302 | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]3[C:29](=[O:30])[C:28]4[C:27]5[C:22](=[CH:23][C:24]([C:31]#[N:32])=[CH:25][CH:26]=5)[NH:21][C:20]=4[C:19]([CH3:34])([CH3:33])[C:18]=3[CH:35]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]3[C:29](=[O:30])[C:28]4[C:27]5[C:22](=[CH:23][C:24]([C:31]#[N:32])=[CH:25][CH:26]=5)[NH:21][C:20]=4[C:19]([CH3:34])([CH3:33])[C:18]=3[CH:35]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3] | null | US09126931B2_1360 | 2,015 | C1CCOC1.CO.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[c:21]2[nH:22][c:23]4[cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29][c:30]4[c:31]2[C:32]3=[O:33])[CH2:34][CH2:35]1.[Pd]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[c:21]2[nH:22][c:23]4[cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29][c:30]4[c:31]2[C:32]3=[O:33])[CH2:34][CH2:35]1 | 0.256623 | C1CCOC1.CC(C)(C)OC(=O)N1CC=C(c2ccc3c(c2)C(C)(C)c2[nH]c4cc(C#N)ccc4c2C3=O)CC1.CO.[Pd]>>CC(C)(C)OC(=O)N1CCC(c2ccc3c(c2)C(C)(C)c2[nH]c4cc(C#N)ccc4c2C3=O)CC1 | C1CCOC1.CC(C)(C)OC(=O)N1CC=C(c2ccc3c(c2)C(C)(C)c2[nH]c4cc(C#N)ccc4c2C3=O)CC1.CO.[Pd]>>CC(C)(C)OC(=O)N1CCC(c2ccc3c(c2)C(C)(C)c2[nH]c4cc(C#N)ccc4c2C3=O)CC1 | US09126931B2_1360grants | 15b942783d163a22c3aeb74300f7e277d90a29b4c0acc3208b02810e | C1CCOC1.CO.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]=[C:11]([c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[c:21]2[nH:22][c:23]4[cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29][c:30]4[c:31]2[C:32]3=[O:33])[CH2:34][CH2:35]1.[Pd] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[c:21]2[nH:22][c:23]4[cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29][c:30]4[c:31]2[C:32]3=[O:33])[CH2:34][CH2:35]1 | ([#7:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:4](-[C:5])-[c:6])>>([#7:1]-[C:2]-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C:5])-[c:6]) | 416666c28bfe999b1c534aac90c614ac7ccaf4b4b7b4d5a1960d352b | 1 | 1 | C1CCOC1.CO.[Pd] | 806 |
304,433 | 989,424 | 1,668,793 | [Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)Cl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:11][CH2:10][C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:26])=[O:25] | null | US09133187B2_0693 | 2,015 | ClCCl.Cl[S:12]([CH3:13])(=[O:14])=[O:15].O.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[c:16]1[cH:17][cH:18][c:19]([F:20])[c:21]([Cl:22])[cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[c:21]([Cl:22])[cH:23]1 | 0.22602 | CC(C)(C)OC(=O)N[C@H](CO)c1ccc(F)c(Cl)c1.CS(=O)(=O)Cl.ClCCl.O>>CC(C)(C)OC(=O)N[C@H](COS(C)(=O)=O)c1ccc(F)c(Cl)c1 | CC(C)(C)OC(=O)N[C@H](CO)c1ccc(F)c(Cl)c1.CS(=O)(=O)Cl.ClCCl.O>>CC(C)(C)OC(=O)N[C@H](COS(C)(=O)=O)c1ccc(F)c(Cl)c1 | US09133187B2_0693grants | 1dd124abb1cd46996eb44ae9d6a57d55566732f8e255a8897bb66c07 | ClCCl.Cl[S:12]([CH3:13])(=[O:14])=[O:15].O.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[c:16]1[cH:17][cH:18][c:19]([F:20])[c:21]([Cl:22])[cH:23]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15])[c:16]1[cH:17][cH:18][c:19]([F:20])[c:21]([Cl:22])[cH:23]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 | ClCCl.O | 0 |
386,322 | 1,044,411 | null | [NH2:1][C:2]1[S:3][C:4]([C:24]2[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=2)=[C:5]([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[CH:10]=[CH:11][CH:12]=2)[N:6]=1.[NH2:31][C:32]1[CH:33]=[CH:34][C:35]2[O:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=2[CH:42]=1>>[NH2:1][C:2]1[S:3][C:4]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:31][C:32]3[CH:33]=[CH:34][C:35]4[O:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=4[CH:42]=3)[N:25]=2)=[C:5]([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])[CH:10]=[CH:11][CH:12]=2)[N:6]=1 | null | US20110098296A1_0812 | 2,011 | Cl[c:27]1[n:26][cH:25][cH:24][c:23](-[c:22]2[c:4](-[c:5]3[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]4[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]4[F:20])[cH:21]3)[n:3][c:2]([NH2:1])[s:41]2)[n:40]1.[NH2:28][c:29]1[cH:30][cH:31][c:32]2[c:33]([cH:34]1)[NH:35][C:36](=[O:37])[CH2:38][O:39]2>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]3[F:20])[cH:21]2)[c:22](-[c:23]2[cH:24][cH:25][n:26][c:27]([NH:28][c:29]3[cH:30][cH:31][c:32]4[c:33]([cH:34]3)[NH:35][C:36](=[O:37])[CH2:38][O:39]4)[n:40]2)[s:41]1 | 0.890528 | Nc1ccc2c(c1)NC(=O)CO2.Nc1nc(-c2cccc(NC(=O)c3c(F)cccc3F)c2)c(-c2ccnc(Cl)n2)s1>>Nc1nc(-c2cccc(NC(=O)c3c(F)cccc3F)c2)c(-c2ccnc(Nc3ccc4c(c3)NC(=O)CO4)n2)s1 | Nc1ccc2c(c1)NC(=O)CO2.Nc1nc(-c2cccc(NC(=O)c3c(F)cccc3F)c2)c(-c2ccnc(Cl)n2)s1>>Nc1nc(-c2cccc(NC(=O)c3c(F)cccc3F)c2)c(-c2ccnc(Nc3ccc4c(c3)NC(=O)CO4)n2)s1 | US20110098296A1_0812apps | 0d82d01837f63f50f8f412ea26476539499431247c440683cee10101 | Cl[c:27]1[n:26][cH:25][cH:24][c:23](-[c:22]2[c:4](-[c:5]3[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]4[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]4[F:20])[cH:21]3)[n:3][c:2]([NH2:1])[s:41]2)[n:40]1.[NH2:28][c:29]1[cH:30][cH:31][c:32]2[c:33]([cH:34]1)[NH:35][C:36](=[O:37])[CH2:38][O:39]2 | [NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]3[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]3[F:20])[cH:21]2)[c:22](-[c:23]2[cH:24][cH:25][n:26][c:27]([NH:28][c:29]3[cH:30][cH:31][c:32]4[c:33]([cH:34]3)[NH:35][C:36](=[O:37])[CH2:38][O:39]4)[n:40]2)[s:41]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[NH;D2;+0:10]-[c:9]1:[c:8]:[c:7]:[c:6](-[#8:5]-[C:4]):[c:12]:[c:11]:1)>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[#8:5]-[c:6]1:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]:[c:12]:1) | f9caff41ce299e10017e28403dac5cd5b0fd9fcc0b6860f463c75587 | 1 | 1 | null | 907 |
434,412 | 1,867,878 | null | NC1C2C(=C(C3C([C@@H](NC(=O)CN4C5C(F)(F)CCC(F)(F)C=5C(C(F)F)=N4)CC4C=C(F)C=C(F)C=4)=NC(SC)=NC=3)C=CC=2)N(C)N=1.[F:50][CH:51]([F:67])[C:52]1[C:53]2[C@H:63]3[CH2:64][C@H:62]3[C:61]([F:66])([F:65])[C:54]=2[N:55]([CH2:57][C:58]([OH:60])=O)[N:56]=1.[NH2:68][C@H:69]([C:79]1[C:84]([C:85]2[CH:86]=[CH:87][C:88]([Cl:100])=[C:89]3[C:93]=2[N:92]([CH3:94])[N:91]=[C:90]3[NH:95][S:96]([CH3:99])(=[O:98])=[O:97])=[CH:83][C:82]([N:101]([CH3:103])[CH3:102])=[C:81]([C:104]#[C:105][C:106]([OH:109])([CH3:108])[CH3:107])[N:80]=1)[CH2:70][C:71]1[CH:76]=[C:75]([F:77])[CH:74]=[C:73]([F:78])[CH:72]=1>>[Cl:100][C:88]1[CH:87]=[CH:86][C:85]([C:84]2[C:79]([C@@H:69]([NH:68][C:58](=[O:60])[CH2:57][N:55]3[C:54]4[C:61]([F:66])([F:65])[C@@H:62]5[CH2:64][C@@H:63]5[C:53]=4[C:52]([CH:51]([F:50])[F:67])=[N:56]3)[CH2:70][C:71]3[CH:72]=[C:73]([F:78])[CH:74]=[C:75]([F:77])[CH:76]=3)=[N:80][C:81]([C:104]#[C:105][C:106]([OH:109])([CH3:107])[CH3:108])=[C:82]([N:101]([CH3:102])[CH3:103])[CH:83]=2)=[C:93]2[C:89]=1[C:90]([NH:95][S:96]([CH3:99])(=[O:98])=[O:97])=[N:91][N:92]2[CH3:94] | null | US20160108030A1_1322 | 2,016 | CSc1ncc(-c2cccc3c(N)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)CCC3(F)F)n1.O[C:35](=[O:36])[CH2:37][n:38]1[n:39][c:40]([CH:41]([F:42])[F:43])[c:44]2[c:45]1[C:46]([F:47])([F:48])[C@@H:49]1[CH2:50][C@H:51]21.[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[c:12]3[c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19][n:20]([CH3:21])[c:22]23)[c:23]([C@H:24]([CH2:25][c:26]2[cH:27][c:28]([F:29])[cH:30][c:31]([F:32])[cH:33]2)[NH2:34])[n:52][c:53]1[C:54]#[C:55][C:56]([CH3:57])([CH3:58])[OH:59]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[c:12]3[c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19][n:20]([CH3:21])[c:22]23)[c:23]([C@H:24]([CH2:25][c:26]2[cH:27][c:28]([F:29])[cH:30][c:31]([F:32])[cH:33]2)[NH:34][C:35](=[O:36])[CH2:37][n:38]2[n:39][c:40]([CH:41]([F:42])[F:43])[c:44]3[c:45]2[C:46]([F:47])([F:48])[C@@H:49]2[CH2:50][C@H:51]32)[n:52][c:53]1[C:54]#[C:55][C:56]([CH3:57])([CH3:58])[OH:59] | 0.080791 | CN(C)c1cc(-c2ccc(Cl)c3c(NS(C)(=O)=O)nn(C)c23)c([C@@H](N)Cc2cc(F)cc(F)c2)nc1C#CC(C)(C)O.CSc1ncc(-c2cccc3c(N)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)CCC3(F)F)n1.O=C(O)Cn1nc(C(F)F)c2c1C(F)(F)[C@@H]1C[C@H]21>>CN(C)c1cc(-c2ccc(Cl)c3c(NS(C)(=O)=O)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)[C@@H]2C[C@H]32)nc1C#CC(C)(C)O | CN(C)c1cc(-c2ccc(Cl)c3c(NS(C)(=O)=O)nn(C)c23)c([C@@H](N)Cc2cc(F)cc(F)c2)nc1C#CC(C)(C)O.CSc1ncc(-c2cccc3c(N)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)CCC3(F)F)n1.O=C(O)Cn1nc(C(F)F)c2c1C(F)(F)[C@@H]1C[C@H]21>>CN(C)c1cc(-c2ccc(Cl)c3c(NS(C)(=O)=O)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)[C@@H]2C[C@H]32)nc1C#CC(C)(C)O | US20160108030A1_1322apps | c4f389ef27f2480058a5ffe5e2f0cb684dfed507222c6ec33140a069 | CSc1ncc(-c2cccc3c(N)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)CCC3(F)F)n1.O[C:35](=[O:36])[CH2:37][n:38]1[n:39][c:40]([CH:41]([F:42])[F:43])[c:44]2[c:45]1[C:46]([F:47])([F:48])[C@@H:49]1[CH2:50][C@H:51]21.[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[c:12]3[c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19][n:20]([CH3:21])[c:22]23)[c:23]([C@H:24]([CH2:25][c:26]2[cH:27][c:28]([F:29])[cH:30][c:31]([F:32])[cH:33]2)[NH2:34])[n:52][c:53]1[C:54]#[C:55][C:56]([CH3:57])([CH3:58])[OH:59] | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[c:12]3[c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[n:19][n:20]([CH3:21])[c:22]23)[c:23]([C@H:24]([CH2:25][c:26]2[cH:27][c:28]([F:29])[cH:30][c:31]([F:32])[cH:33]2)[NH:34][C:35](=[O:36])[CH2:37][n:38]2[n:39][c:40]([CH:41]([F:42])[F:43])[c:44]3[c:45]2[C:46]([F:47])([F:48])[C@@H:49]2[CH2:50][C@H:51]32)[n:52][c:53]1[C:54]#[C:55][C:56]([CH3:57])([CH3:58])[OH:59] | ([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 | 1 | 1 | CSc1ncc(-c2cccc3c(N)nn(C)c23)c([C@H](Cc2cc(F)cc(F)c2)NC(=O)Cn2nc(C(F)F)c3c2C(F)(F)CCC3(F)F)n1 | 230 |
202,791 | 690,543 | 1,138,671 | Br[CH2:2][C@@H:3]([CH3:6])[CH2:4][OH:5].C([O-])([O-])=O.[K+].[K+].[CH3:13][C:14]1([CH3:28])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[O:15]1>CC#N>[CH3:6][C@H:3]([CH2:2][O:27][C:24]1[CH:23]=[CH:22][C:21]([B:16]2[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:28])([CH3:13])[O:15]2)=[CH:26][CH:25]=1)[CH2:4][OH:5] | |f:1.2.3| | US08076331B2_0208 | 2,011 | Br[CH2:5][C@@H:2]([CH3:1])[CH2:3][OH:4].CC#N.O=C([O-])[O-].[K+].[K+].[OH:6][c:7]1[cH:8][cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20][cH:21]1>>[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20][cH:21]1 | 0.312306 | CC#N.CC1(C)OB(c2ccc(O)cc2)OC1(C)C.C[C@@H](CO)CBr.O=C([O-])[O-]~[K+]~[K+]>>C[C@@H](CO)COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | CC#N.CC1(C)OB(c2ccc(O)cc2)OC1(C)C.C[C@@H](CO)CBr.O=C([O-])[O-].[K+].[K+]>>C[C@@H](CO)COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1 | US08076331B2_0208grants | 5c888e6e079c8b40b49fe09be819a1e6d28e87c27c312d2ae76e370d | Br[CH2:5][C@@H:2]([CH3:1])[CH2:3][OH:4].CC#N.O=C([O-])[O-].[K+].[K+].[OH:6][c:7]1[cH:8][cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20][cH:21]1 | [CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)[cH:20][cH:21]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 |
176,325 | 614,391 | 1,018,910 | [Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(O)C.[BH4-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH2:7][OH:8])[CH:9]=1 | |f:2.3| | US07807690B2_0532 | 2,010 | C1CCOC1.CCO.Cl.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH:9]=[O:10])[c:11]1[OH:12].[Na+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH2:9][OH:10])[c:11]1[OH:12] | 0.995643 | C1CCOC1.CCO.COc1cc(Br)cc(C=O)c1O.Cl.[BH4-]~[Na+]>>COc1cc(Br)cc(CO)c1O | C1CCOC1.CCO.COc1cc(Br)cc(C=O)c1O.Cl.[BH4-].[Na+]>>COc1cc(Br)cc(CO)c1O | US07807690B2_0532grants | 8a15535f32db57dccefb7fa249456020dba7d79b02003b4f38ccae16 | C1CCOC1.CCO.Cl.[BH4-].[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH:9]=[O:10])[c:11]1[OH:12].[Na+] | [CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([CH2:9][OH:10])[c:11]1[OH:12] | ([OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]) | 840c26c06ae3d1e03b5c3844632a3543b6d18e6db9d7ee28fbdda31c | 1 | 1 | C1CCOC1.CCO.Cl.[BH4-].[Na+] | 356 |
395,576 | 1,265,635 | null | I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([NH:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[O:18])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:28]([OH:31])[C:29]#[CH:30]>CCN(CC)CC.CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:31][CH2:28][C:29]#[C:30][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]2[CH:27]=[CH:26][C:16]([C:17]([NH:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[O:18])=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1 | |^1:52,71| | US20120225862A1_0690 | 2,012 | CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:22]1[cH:21][cH:20][c:19]([S:16]([NH:15][CH2:14][c:13]2[cH:12][cH:11][c:10]([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][n:8][cH:9]3)[cH:30][cH:29]2)(=[O:17])=[O:18])[cH:28][cH:27]1.[CH:23]#[C:24][CH2:25][OH:26].[Cu]I>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]([C:23]#[C:24][CH2:25][OH:26])[cH:27][cH:28]2)[cH:29][cH:30]1 | 0.548114 | C#CCO.CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(Nc1cccnc1)c1ccc(CNS(=O)(=O)c2ccc(I)cc2)cc1.[Cu]I>>O=C(Nc1cccnc1)c1ccc(CNS(=O)(=O)c2ccc(C#CCO)cc2)cc1 | C#CCO.CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(Nc1cccnc1)c1ccc(CNS(=O)(=O)c2ccc(I)cc2)cc1.[Cu]I>>O=C(Nc1cccnc1)c1ccc(CNS(=O)(=O)c2ccc(C#CCO)cc2)cc1 | US20120225862A1_0690apps | 50d6b3e2883b71df9c598ffbb96e8df2bd217342362a1d186e4463eb | CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.I[c:22]1[cH:21][cH:20][c:19]([S:16]([NH:15][CH2:14][c:13]2[cH:12][cH:11][c:10]([C:2](=[O:1])[NH:3][c:4]3[cH:5][cH:6][cH:7][n:8][cH:9]3)[cH:30][cH:29]2)(=[O:17])=[O:18])[cH:28][cH:27]1.[CH:23]#[C:24][CH2:25][OH:26].[Cu]I | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][c:22]([C:23]#[C:24][CH2:25][OH:26])[cH:27][cH:28]2)[cH:29][cH:30]1 | ([C:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(I-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 342ec13d6dc46f8caedd04911cf98542ef6704fb7da33fd6b60ef2c6 | 1 | 1 | CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I | 664 |
343,713 | 369,009 | null | C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CCO.[OH-].[Pd+2].[OH-]>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1 | |f:3.4.5| | US20060160853A1_0047 | 2,006 | CCO.[H][H].[OH-].[OH-].[Pd+2].c1ccc(C[N:12]2[CH2:11][CH2:10][CH:9]([CH2:8][c:7]3[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]3)[CH2:14][CH2:13]2)cc1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | 0.982512 | CCO.Fc1ccccc1CC1CCN(Cc2ccccc2)CC1.[H][H].[OH-]~[OH-]~[Pd+2]>>Fc1ccccc1CC1CCNCC1 | CCO.Fc1ccccc1CC1CCN(Cc2ccccc2)CC1.[H][H].[OH-].[OH-].[Pd+2]>>Fc1ccccc1CC1CCNCC1 | US20060160853A1_0047apps | de59fd261a1c215a22395fefff478fbc3c36fc8101d849bb3bc5fe42 | CCO.[H][H].[OH-].[OH-].[Pd+2].c1ccc(C[N:12]2[CH2:11][CH2:10][CH:9]([CH2:8][c:7]3[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]3)[CH2:14][CH2:13]2)cc1 | [F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | ([C:1]-[NH;D2;+0:2]-[C:3])>>([C:1]-[N;H0;D3;+0:2](-[C:3])-C-c1:c:c:c:c:c:1) | f58207c6c64a5b48e40756ac3ba50fe69cdf9b1d18b6063ebd95ff15 | 1 | 1 | CCO.[H][H].[OH-].[OH-].[Pd+2] | 84 |
80,241 | 324,538 | 549,998 | [CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8]CC)=[O:7].S(=O)(=O)(O)O.C(O)(=O)C>O>[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7] | null | US06369110B1_ | 2,002 | CC(=O)O.CC[O:8][C:6]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[O:7].O.O=S(=O)(O)O>>[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | 0.945144 | CC(=O)O.CCOC(=O)CCCC(C)c1ccccc1.O.O=S(=O)(O)O>>CC(CCCC(=O)O)c1ccccc1 | CC(=O)O.CCOC(=O)CCCC(C)c1ccccc1.O.O=S(=O)(O)O>>CC(CCCC(=O)O)c1ccccc1 | US06369110B1_grants | 26ccd91f3055ab4f5e8d6a40844969c2b2415f3648b346e68b9a83d7 | CC(=O)O.CC[O:8][C:6]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[O:7].O.O=S(=O)(O)O | [CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]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 | CC(=O)O.O.O=S(=O)(O)O | 7 |
207,928 | 704,221 | 1,160,473 | [CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([C:23](OC)=[O:24])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([CH2:23][OH:24])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | |f:1.2.3.4.5.6| | US08124617B2_0764 | 2,012 | C1CCOC1.CO[C:25]([c:24]1[cH:23][cH:22][c:21]2[n:20][c:19](-[c:18]3[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[cH:17]3)[nH:29][c:28]2[n:27]1)=[O:26].O.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH: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][c:18]1-[c:19]1[n:20][c:21]2[cH:22][cH:23][c:24]([CH2:25][OH:26])[n:27][c:28]2[nH:29]1 | 0.588711 | C1CCOC1.COC(=O)c1ccc2nc(-c3cc(OCc4ccccc4)ccc3OC(C)C)[nH]c2n1.O.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>CC(C)Oc1ccc(OCc2ccccc2)cc1-c1nc2ccc(CO)nc2[nH]1 | C1CCOC1.COC(=O)c1ccc2nc(-c3cc(OCc4ccccc4)ccc3OC(C)C)[nH]c2n1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>CC(C)Oc1ccc(OCc2ccccc2)cc1-c1nc2ccc(CO)nc2[nH]1 | US08124617B2_0764grants | 4614cc25dba5cc4d9a97525e6617f1cfef6275bc692876ac4c29d232 | C1CCOC1.CO[C:25]([c:24]1[cH:23][cH:22][c:21]2[n:20][c:19](-[c:18]3[c:5]([O:4][CH:2]([CH3:1])[CH3:3])[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[cH:17]3)[nH:29][c:28]2[n:27]1)=[O:26].O.[Al+3].[H-].[H-].[H-].[H-].[Li+] | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH: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][c:18]1-[c:19]1[n:20][c:21]2[cH:22][cH:23][c:24]([CH2:25][OH:26])[n:27][c:28]2[nH:29]1 | ([#7;a:4]:[c:3]-[CH2;D2;+0:1]-[OH;D1;+0:2])>>(C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]:[#7;a:4]) | 1508c5b0cc30fd12bcd85a481ecdf2409646ced61648be6cfb359dd8 | 1 | 1 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 546 |
89,671 | 353,807 | 603,302 | [C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13](/[C:16](/[CH3:36])=[CH:17]/[CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C@H:27]([O:33][CH2:34][CH3:35])[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+]>>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13](/[C:16](/[CH3:36])=[CH:17]/[CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C@H:27]([O:33][CH2:34][CH3:35])[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2] | |f:1.2| | US06555577B1_ | 2,003 | CC[O:34][C:32]([C@@H:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11]/[CH:12]=[C:13](\[CH3:14])[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1)=[O:33].[Na+].[OH-]>>[CH3:1][CH2:2][O:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11]/[CH:12]=[C:13](\[CH3:14])[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1)[C:32](=[O:33])[OH:34] | 0.93252 | CCOC(=O)[C@H](Cc1ccc(OC/C=C(\C)c2ccc(-c3cccc(C(C)=O)c3)cc2)cc1)OCC.[Na+]~[OH-]>>CCO[C@@H](Cc1ccc(OC/C=C(\C)c2ccc(-c3cccc(C(C)=O)c3)cc2)cc1)C(=O)O | CCOC(=O)[C@H](Cc1ccc(OC/C=C(\C)c2ccc(-c3cccc(C(C)=O)c3)cc2)cc1)OCC.[Na+].[OH-]>>CCO[C@@H](Cc1ccc(OC/C=C(\C)c2ccc(-c3cccc(C(C)=O)c3)cc2)cc1)C(=O)O | US06555577B1_grants | c4004d415d68d7c4d6b316678768f084d3e58d08842cdedf008d70a8 | CC[O:34][C:32]([C@@H:4]([O:3][CH2:2][CH3:1])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11]/[CH:12]=[C:13](\[CH3:14])[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1)=[O:33].[Na+].[OH-] | [CH3:1][CH2:2][O:3][C@@H:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11]/[CH:12]=[C:13](\[CH3:14])[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]([C:24]([CH3:25])=[O:26])[cH:27]3)[cH:28][cH:29]2)[cH:30][cH:31]1)[C:32](=[O:33])[OH:34] | ([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 | [Na+].[OH-] | 7 |
149,752 | 535,761 | 896,951 | C[O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([F:13])([F:14])[F:15] | null | US07528129B2_0724 | 2,009 | C[O:8][c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13].O=C(O)CC(O)(CC(=O)O)C(=O)O>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | 0.288428 | COc1ccc(C(=O)O)cc1C(F)(F)F.O=C(O)CC(O)(CC(=O)O)C(=O)O>>O=C(O)c1ccc(O)c(C(F)(F)F)c1 | COc1ccc(C(=O)O)cc1C(F)(F)F.O=C(O)CC(O)(CC(=O)O)C(=O)O>>O=C(O)c1ccc(O)c(C(F)(F)F)c1 | US07528129B2_0724grants | 3b0b26e7dce8f4eca324e76851f21046bbca4e16a4716be4d87e2cdb | C[O:8][c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13].O=C(O)CC(O)(CC(=O)O)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | O=C(O)CC(O)(CC(=O)O)C(=O)O | 48 |
324,337 | 1,053,929 | 1,788,924 | [CH3:1][C:2]1[CH:3]=[C:4]([C:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH:8]=2)[S:5][CH:6]=1.C(=O)(O)[O-].[Na+]>>[CH3:1][C:2]1[CH:3]=[C:4]([C:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH:8]=2)[S:5][CH:6]=1 | |f:1.2| | US09403798B2_1089 | 2,016 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH:7]=[C:6]([c:5]2[s:4][cH:3][c:2]([CH3:1])[cH:12]2)[CH2:11][CH2:10]1.O=C([O-])O.[Na+]>>[CH3:1][c:2]1[cH:3][s:4][c:5]([C:6]2=[CH:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12]1 | 0.982977 | Cc1csc(C2=CCN(C(=O)OC(C)(C)C)CC2)c1.O=C([O-])O~[Na+]>>Cc1csc(C2=CCNCC2)c1 | Cc1csc(C2=CCN(C(=O)OC(C)(C)C)CC2)c1.O=C([O-])O.[Na+]>>Cc1csc(C2=CCNCC2)c1 | US09403798B2_1089grants | 3be7e8e3d7cb3ebd0667c524c169f1a4ec55c0844494826a01437622 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH:7]=[C:6]([c:5]2[s:4][cH:3][c:2]([CH3:1])[cH:12]2)[CH2:11][CH2:10]1.O=C([O-])O.[Na+] | [CH3:1][c:2]1[cH:3][s:4][c:5]([C:6]2=[CH:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12]1 | ([C:2]-[NH;D2;+0:1]-[C:3]-[C:4]=[C:5])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]-[C:4]=[C:5]) | 7138a61409cd3d87bff9ab3b2cf722d6a91c1cf3d022dc68894a7a8a | 1 | 1 | O=C([O-])O.[Na+] | 800 |
155,960 | 554,102 | 926,499 | [H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]1>CN(C=O)C>[CH3:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)[CH2:16][CH2:15]1 | |f:0.1| | US07592373B2_0594 | 2,009 | CN(C)C=O.F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1.[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][OH:8])[CH2:18][CH2:19]1.[H-].[Na+]>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | 0.831017 | CC1CCN(CCO)CC1.CN(C)C=O.O=[N+]([O-])c1ccc(F)cc1.[H-]~[Na+]>>CC1CCN(CCOc2ccc([N+](=O)[O-])cc2)CC1 | CC1CCN(CCO)CC1.CN(C)C=O.O=[N+]([O-])c1ccc(F)cc1.[H-].[Na+]>>CC1CCN(CCOc2ccc([N+](=O)[O-])cc2)CC1 | US07592373B2_0594grants | 7b6206fe7d5c0b8ff00c67705d3e94171df066e7de2e0ed994a2eff8 | CN(C)C=O.F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1.[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][OH:8])[CH2:18][CH2:19]1.[H-].[Na+] | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | ([C:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[OH;D1;+0:5]) | 5e910f78c09147f95443e74bed5b26e7557d68f73dba61bcb03d2b4e | 1 | 1 | CN(C)C=O.[H-].[Na+] | 485 |
151,651 | 541,602 | 906,657 | C([O-])([O-])=O.[Cs+].[Cs+].[F:7][C:8]([F:24])([F:23])[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1)[OH:10].[NH2:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[C:28]([Cl:33])[N:27]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:33][C:28]1[CH:29]=[C:30]([O:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)[C:8]([F:7])([F:23])[F:24])[N:31]=[C:26]([NH2:25])[N:27]=1 | |f:0.1.2| | US07553840B2_0275 | 2,009 | C1CCOC1.CCOC(C)=O.Cl[c:13]1[cH:14][c:15]([Cl:16])[n:17][c:18]([NH2:19])[n:20]1.O.O=C([O-])[O-].[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]([OH:12])[C:21]([F:22])([F:23])[F:24])[cH:25][n:26]1.[Cs+].[Cs+]>>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]([O:12][c:13]2[cH:14][c:15]([Cl:16])[n:17][c:18]([NH2:19])[n:20]2)[C:21]([F:22])([F:23])[F:24])[cH:25][n:26]1 | 0.240058 | C1CCOC1.CCOC(C)=O.Cn1cc(-c2ccccc2C(O)C(F)(F)F)cn1.Nc1nc(Cl)cc(Cl)n1.O.O=C([O-])[O-]~[Cs+]~[Cs+]>>Cn1cc(-c2ccccc2C(Oc2cc(Cl)nc(N)n2)C(F)(F)F)cn1 | C1CCOC1.CCOC(C)=O.Cn1cc(-c2ccccc2C(O)C(F)(F)F)cn1.Nc1nc(Cl)cc(Cl)n1.O.O=C([O-])[O-].[Cs+].[Cs+]>>Cn1cc(-c2ccccc2C(Oc2cc(Cl)nc(N)n2)C(F)(F)F)cn1 | US07553840B2_0275grants | 3ebd04a082b5b7bc7abb1e414631c1f2999fbe371caa3b305a5b409b | C1CCOC1.CCOC(C)=O.Cl[c:13]1[cH:14][c:15]([Cl:16])[n:17][c:18]([NH2:19])[n:20]1.O.O=C([O-])[O-].[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]([OH:12])[C:21]([F:22])([F:23])[F:24])[cH:25][n:26]1.[Cs+].[Cs+] | [CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH:11]([O:12][c:13]2[cH:14][c:15]([Cl:16])[n:17][c:18]([NH2:19])[n:20]2)[C:21]([F:22])([F:23])[F:24])[cH:25][n:26]1 | ([C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C:7]-[OH;D1;+0:8]) | 5143b901619ce0acc66a8a625982dda04978c2b35cb026eacddddf7e | 1 | 1 | C1CCOC1.CCOC(C)=O.O.O=C([O-])[O-].[Cs+].[Cs+] | 653 |
396,958 | 1,301,456 | null | [CH:1]1([O:6][C:7]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=2[CH3:16])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO.[Pd]>[CH:1]1([O:6][C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=2[CH3:16])[NH2:13])[CH2:5][CH2:4][CH2:3][CH2:2]1 | |f:1.2| | US20120295903A1_1235 | 2,012 | CO.O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:7]1.[BH4-].[Na+].[Pd]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:7][c:8]1[O:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | 0.97425 | CO.Cc1ccc([N+](=O)[O-])cc1OC1CCCC1.[BH4-]~[Na+].[Pd]>>Cc1ccc(N)cc1OC1CCCC1 | CO.Cc1ccc([N+](=O)[O-])cc1OC1CCCC1.[BH4-].[Na+].[Pd]>>Cc1ccc(N)cc1OC1CCCC1 | US20120295903A1_1235apps | 7f60d7b78a5f19ebd01b91a5f064ef0ea65be542cd5b6d235e8a3870 | CO.O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:7]1.[BH4-].[Na+].[Pd] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:7][c:8]1[O:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[BH4-].[Na+].[Pd] | 1 |
76,472 | 311,252 | 527,989 | [CH3:13][C:12]([O:11][C:9](O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:10])([CH3:15])[CH3:14].Cl.Cl.[NH2:18][C:19]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1>O1CCOCC1>[CH2:25]([N:22]1[CH2:21][CH2:20][C:19]([NH:18][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:24][CH2:23]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1 | |f:1.2.3| | US06294537B1_ | 2,001 | C1COCCO1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].Cl.Cl.[NH2:8][C:9]1([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1 | 0.177354 | C1COCCO1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cl~Cl~NC1(c2ccccc2)CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)NC1(c2ccccc2)CCN(Cc2ccccc2)CC1 | C1COCCO1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cl.Cl.NC1(c2ccccc2)CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)NC1(c2ccccc2)CCN(Cc2ccccc2)CC1 | US06294537B1_grants | 503e91788fa0d9d8d1b779fe4758db1b464e08c6995d89b9db912fce | C1COCCO1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].Cl.Cl.[NH2:8][C:9]1([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1 | ([C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[c:15]:1)>>(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]).([NH2;D1;+0:8]-[C:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[c:14]:[c:15]:1) | 99fbb0070a9da6d11e987da55ba5465058f85284f4cc3723d6e3da97 | 1 | 1 | C1COCCO1.Cl.Cl | 686 |
432,735 | 1,858,018 | null | Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17](B(O)O)[CH:16]=1>>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[C:6]([CH3:14])([CH3:13])[C:7]1=[O:12] | null | US20160095844A1_0365 | 2,016 | Br[c:11]1[cH:10][cH:9][c:8]2[c:19]([cH:18]1)[N:2]([CH3:1])[C:3](=[O:4])[C:5]2([CH3:6])[CH3:7].OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][N:2]1[C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[cH:18][c:19]21 | 0.716338 | CN1C(=O)C(C)(C)c2ccc(Br)cc21.OB(O)c1cccnc1>>CN1C(=O)C(C)(C)c2ccc(-c3cccnc3)cc21 | CN1C(=O)C(C)(C)c2ccc(Br)cc21.OB(O)c1cccnc1>>CN1C(=O)C(C)(C)c2ccc(-c3cccnc3)cc21 | US20160095844A1_0365apps | 1e846a97ba9778615dd7af84db6db8df4196068f9f144efe3e1c2dd0 | Br[c:11]1[cH:10][cH:9][c:8]2[c:19]([cH:18]1)[N:2]([CH3:1])[C:3](=[O:4])[C:5]2([CH3:6])[CH3:7].OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1 | [CH3:1][N:2]1[C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[cH:18][c:19]21 | ([#7;a:7]:[c:6]:[c;H0;D3;+0:4](:[c:5])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[c;H0;D3;+0:4](:[c:5]):[c:6]:[#7;a:7]) | 999289af95239798f3333fa37b4d8ce6e1e29a507b8e980f7a6b0048 | 1 | 1 | null | 899 |
158,072 | 560,720 | 936,309 | [CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][OH:14])=[CH:7][CH:6]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:9][CH:10]=1 | null | US07612212B2_0403 | 2,009 | Cl[S:22]([CH3:23])(=[O:24])=[O:25].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][OH:21])[cH:26][cH:27]1.c1ccncc1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][O:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26][cH:27]1 | 0.231385 | COC(=O)[C@H](NC(=O)OC(C)(C)C)c1ccc(OCCO)cc1.CS(=O)(=O)Cl.c1ccncc1>>COC(=O)[C@H](NC(=O)OC(C)(C)C)c1ccc(OCCOS(C)(=O)=O)cc1 | COC(=O)[C@H](NC(=O)OC(C)(C)C)c1ccc(OCCO)cc1.CS(=O)(=O)Cl.c1ccncc1>>COC(=O)[C@H](NC(=O)OC(C)(C)C)c1ccc(OCCOS(C)(=O)=O)cc1 | US07612212B2_0403grants | 1f008a1f27f1de42706381144b382cbe96b561ea09337e0d1793391e | Cl[S:22]([CH3:23])(=[O:24])=[O:25].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][OH:21])[cH:26][cH:27]1.c1ccncc1 | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][O:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26][cH:27]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 | c1ccncc1 | 0 |
297,720 | 968,781 | 1,630,811 | [Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:19])[CH2:13][CH2:14][C:15](OC)=[O:16].[BH4-].[Na+].C(OCC)(=O)C>CO>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][OH:16] | |f:1.2| | US09062028B2_0890 | 2,015 | CCOC(C)=O.CO.CO[C:5]([CH2:4][CH2:3][C:2](=[O:1])[N:7]1[CH2:8][CH2:9][CH2:10][c:11]2[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]21)=[O:6].[BH4-].[Na+]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][OH:6])[N:7]1[CH2:8][CH2:9][CH2:10][c:11]2[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]21 | 0.799314 | CCOC(C)=O.CO.COC(=O)CCC(=O)N1CCCc2c(Br)cccc21.[BH4-]~[Na+]>>O=C(CCCO)N1CCCc2c(Br)cccc21 | CCOC(C)=O.CO.COC(=O)CCC(=O)N1CCCc2c(Br)cccc21.[BH4-].[Na+]>>O=C(CCCO)N1CCCc2c(Br)cccc21 | US09062028B2_0890grants | 9b74d1be823d85678bf0174e78f327ff2d4021336f900bde6cfa67fa | CCOC(C)=O.CO.CO[C:5]([CH2:4][CH2:3][C:2](=[O:1])[N:7]1[CH2:8][CH2:9][CH2:10][c:11]2[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]21)=[O:6].[BH4-].[Na+] | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5][OH:6])[N:7]1[CH2:8][CH2:9][CH2:10][c:11]2[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]21 | ([C:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;H0;D1;+0:3]) | ace077327b65885e2493775e77cea5434d2da2918de8308af58629a6 | 1 | 1 | CCOC(C)=O.CO.[BH4-].[Na+] | 343 |
258,705 | 855,338 | 1,423,390 | [OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][OH:15])[CH2:3]1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:3]1 | null | US08648074B2_1098 | 2,014 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:25][cH:24]1)(=[O:7])=[O:8].[OH:9][CH2:10][C@@H:11]1[CH2:12][C@@H:13]([OH:14])[CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].c1ccncc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][C@@H:11]2[CH2:12][C@@H:13]([OH:14])[CH2:15][N:16]2[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]1 | 0.182399 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1CO.Cc1ccc(S(=O)(=O)Cl)cc1.c1ccncc1>>Cc1ccc(S(=O)(=O)OC[C@@H]2C[C@@H](O)CN2C(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1CO.Cc1ccc(S(=O)(=O)Cl)cc1.c1ccncc1>>Cc1ccc(S(=O)(=O)OC[C@@H]2C[C@@H](O)CN2C(=O)OC(C)(C)C)cc1 | US08648074B2_1098grants | 7af9863d84ea12d97114ae5d7bbe57342eeeace6b1348ccb9ae6e720 | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:25][cH:24]1)(=[O:7])=[O:8].[OH:9][CH2:10][C@@H:11]1[CH2:12][C@@H:13]([OH:14])[CH2:15][N:16]1[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].c1ccncc1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][C@@H:11]2[CH2:12][C@@H:13]([OH:14])[CH2:15][N:16]2[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[OH;D1;+0:6]) | 2a680215c1c69f116045ff1696194ac3ca890d5406b0abc3856bedc8 | 1 | 1 | c1ccncc1 | 197 |
382,058 | 966,552 | null | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1 | null | US20100278733A1_0065 | 2,010 | CCO.Cl[Sn]Cl.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | 0.900105 | CCO.Cl[Sn]Cl.O=C(C=Cc1ccc(Br)cc1)c1ccc([N+](=O)[O-])cc1>>Nc1ccc(C(=O)C=Cc2ccc(Br)cc2)cc1 | CCO.Cl[Sn]Cl.O=C(C=Cc1ccc(Br)cc1)c1ccc([N+](=O)[O-])cc1>>Nc1ccc(C(=O)C=Cc2ccc(Br)cc2)cc1 | US20100278733A1_0065apps | beaf51e8adac5ec830f909768e170410ba17a8c42636e4990a016a9b | CCO.Cl[Sn]Cl.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.Cl[Sn]Cl | 1 |
112,481 | 422,920 | 720,302 | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.S(=O)(=O)(O)O.O.[NH4+].[CH3:22]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([O:14][CH3:22])=[O:13])=[CH:2]1 | |f:2.3| | US07037929B1_0678 | 2,006 | O.O=S(=O)(O)O.O[C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12.[CH3:1][OH:2].[NH4+]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | 0.703325 | CO.O=C(O)CCc1c[nH]c2ccccc12.O=S(=O)(O)O.O~[NH4+]>>COC(=O)CCc1c[nH]c2ccccc12 | CO.O.O=C(O)CCc1c[nH]c2ccccc12.O=S(=O)(O)O.[NH4+]>>COC(=O)CCc1c[nH]c2ccccc12 | US07037929B1_0678grants | 11f90f577ef669a23393c074dfcd623ec3eb6ae42c78621ca4a71fa1 | O.O=S(=O)(O)O.O[C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12.[CH3:1][OH:2].[NH4+] | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C;D1;H3:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | O.O=S(=O)(O)O.[NH4+] | 17 |
63,974 | 268,623 | 455,640 | [C:1]12([C:11]3[CH:12]=[C:13]([C:19]4([CH3:32])[C:23]5[CH:24]=[CH:25][C:26]([C:28]([O:30]C)=[O:29])=[CH:27][C:22]=5[O:21][CH2:20]4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].[OH-].[Li+]>>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4([CH3:32])[C:23]5[CH:24]=[CH:25][C:26]([C:28]([OH:30])=[O:29])=[CH:27][C:22]=5[O:21][CH2:20]4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2 | |f:1.2,3.4| | US05981776_ | 1,999 | C[O:16][C:14]([c:13]1[cH:12][c:11]2[c:19]([cH:18][cH:17]1)[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([C:22]34[CH2:23][CH:24]5[CH2:25][CH:26]([CH2:27][CH:28]([CH2:29]5)[CH2:30]3)[CH2:31]4)[cH:20]1)([CH3:8])[CH2:9][O:10]2)=[O:15].[Li+].[Na+].[OH-].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][O:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18][c:19]32)[cH:20][c:21]1[C:22]12[CH2:23][CH:24]3[CH2:25][CH:26]([CH2:27][CH:28]([CH2:29]3)[CH2:30]1)[CH2:31]2 | 0.692441 | COC(=O)c1ccc2c(c1)OCC2(C)c1ccc(OC)c(C23CC4CC(CC(C4)C2)C3)c1.[Li+]~[OH-].[Na+]~[OH-]>>COc1ccc(C2(C)COc3cc(C(=O)O)ccc32)cc1C12CC3CC(CC(C3)C1)C2 | COC(=O)c1ccc2c(c1)OCC2(C)c1ccc(OC)c(C23CC4CC(CC(C4)C2)C3)c1.[Li+].[Na+].[OH-].[OH-]>>COc1ccc(C2(C)COc3cc(C(=O)O)ccc32)cc1C12CC3CC(CC(C3)C1)C2 | US05981776_grants | 64c5beb4a2137cda9dc772ce548ebf0c0e5604b229558cf76bef9e74 | C[O:16][C:14]([c:13]1[cH:12][c:11]2[c:19]([cH:18][cH:17]1)[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([C:22]34[CH2:23][CH:24]5[CH2:25][CH:26]([CH2:27][CH:28]([CH2:29]5)[CH2:30]3)[CH2:31]4)[cH:20]1)([CH3:8])[CH2:9][O:10]2)=[O:15].[Li+].[Na+].[OH-].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2([CH3:8])[CH2:9][O:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18][c:19]32)[cH:20][c:21]1[C:22]12[CH2:23][CH:24]3[CH2:25][CH:26]([CH2:27][CH:28]([CH2:29]3)[CH2:30]1)[CH2:31]2 | ([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 | [Li+].[Na+].[OH-].[OH-] | 247 |
405,866 | 1,535,928 | null | Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1.[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1NC(=O)C=C2>CS(C)=O.O.CCOC(C)=O.[Cu]I>[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][N:33]([C:2]2[CH:3]=[CH:4][C:5]3[O:14][C:13]4[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=4[C:6]=3[CH:7]=2)[C:32](=[O:36])[CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1 | |f:2.3.4| | US20140163012A1_0533 | 2,014 | Br[c:16]1[cH:15][cH:14][c:13]2[o:12][c:11]3[c:34]([c:33]2[cH:32]1)[CH2:35][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3.CCOC(C)=O.CS(C)=O.O.O=C([O-])[O-].O=c1ccc2cccc(O)c2[nH]1.[Cu]I.[K+].[K+].[nH:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][c:30]1=[O:31]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[o:12][c:13]3[cH:14][cH:15][c:16](-[n:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29][c:30]4=[O:31])[cH:32][c:33]3[c:34]2[CH2:35]1 | 0.368784 | CC(C)(C)OC(=O)N1CCc2oc3ccc(Br)cc3c2C1.CCOC(C)=O.CS(C)=O.O.O=C([O-])[O-]~[K+]~[K+].O=c1cc(OCc2ccccc2)cc[nH]1.O=c1ccc2cccc(O)c2[nH]1.[Cu]I>>CC(C)(C)OC(=O)N1CCc2oc3ccc(-n4ccc(OCc5ccccc5)cc4=O)cc3c2C1 | CC(C)(C)OC(=O)N1CCc2oc3ccc(Br)cc3c2C1.CCOC(C)=O.CS(C)=O.O.O=C([O-])[O-].O=c1cc(OCc2ccccc2)cc[nH]1.O=c1ccc2cccc(O)c2[nH]1.[Cu]I.[K+].[K+]>>CC(C)(C)OC(=O)N1CCc2oc3ccc(-n4ccc(OCc5ccccc5)cc4=O)cc3c2C1 | US20140163012A1_0533apps | 51e56a4fb753b6699cf1978811d433441212d032794204fd8f0ca560 | Br[c:16]1[cH:15][cH:14][c:13]2[o:12][c:11]3[c:34]([c:33]2[cH:32]1)[CH2:35][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3.CCOC(C)=O.CS(C)=O.O.O=C([O-])[O-].O=c1ccc2cccc(O)c2[nH]1.[Cu]I.[K+].[K+].[nH:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][c:30]1=[O:31] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[o:12][c:13]3[cH:14][cH:15][c:16](-[n:17]4[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:29][c:30]4=[O:31])[cH:32][c:33]3[c:34]2[CH2:35]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[n;H0;D3;+0:5](:[c:4]):[c:6])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([c:4]:[nH;D2;+0:5]:[c:6]) | 3fe034cccad6980ec2d3a1de437611ce8e22696c412d2117aaa7c4a7 | 1 | 1 | CCOC(C)=O.CS(C)=O.O.O=C([O-])[O-].O=c1ccc2cccc(O)c2[nH]1.[Cu]I.[K+].[K+] | 349 |
385,776 | 1,030,450 | null | [CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]#[C:9][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].CCOCC>CO.O>[C:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1])#[CH:9] | |f:1.2.3| | US20110071150A1_0681 | 2,011 | CCOCC.CO.C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH3:9].O.O=C([O-])[O-].[K+].[K+]>>[CH:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH3:9] | 0.996571 | CCOCC.CO.Cc1ccncc1C#C[Si](C)(C)C.O.O=C([O-])[O-]~[K+]~[K+]>>C#Cc1cnccc1C | CCOCC.CO.Cc1ccncc1C#C[Si](C)(C)C.O.O=C([O-])[O-].[K+].[K+]>>C#Cc1cnccc1C | US20110071150A1_0681apps | d8fec953dc20c8d8c2be1e2bdfbd36e67d9b70069dd996c983393b8b | CCOCC.CO.C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH3:9].O.O=C([O-])[O-].[K+].[K+] | [CH:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH3:9] | ([C:2]#[CH;D1;+0:1])>>(C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]) | 369c1d52dad09f90f7281506a651d2a503963767498d914edaae47e1 | 1 | 1 | CCOCC.CO.O.O=C([O-])[O-].[K+].[K+] | 337 |
346,971 | 422,502 | null | C[O:2][C:3]1[C:12]2[O:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[C:12]2[O:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1 | null | US20070010670A1_3069 | 2,007 | BrB(Br)Br.C[O:7][c:6]1[c:5]2[c:11]([cH:10][cH:9][cH:8]1)[NH:12][C:2](=[O:1])[CH2:3][O:4]2.ClCCl.O>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]2[NH:12]1 | 0.986846 | BrB(Br)Br.COc1cccc2c1OCC(=O)N2.ClCCl.O>>O=C1COc2c(O)cccc2N1 | BrB(Br)Br.COc1cccc2c1OCC(=O)N2.ClCCl.O>>O=C1COc2c(O)cccc2N1 | US20070010670A1_3069apps | 981df4669a19b842d2a18ff2345a8a100df7a290679ed2b8a3a77ff4 | BrB(Br)Br.C[O:7][c:6]1[c:5]2[c:11]([cH:10][cH:9][cH:8]1)[NH:12][C:2](=[O:1])[CH2:3][O:4]2.ClCCl.O | [O:1]=[C:2]1[CH2:3][O:4][c:5]2[c:6]([OH:7])[cH:8][cH:9][cH:10][c:11]2[NH:12]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCl.O | 48 |
414,663 | 1,702,055 | null | [F:1][C:2]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=2)=[O:35])=[CH:29][C:3]=1[C:4]([C:6]1[CH:15]=[C:14]2[C:9]([N:10]=[CH:11][C:12]([N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[N:13]2)=[CH:8][CH:7]=1)=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=2)=[O:35])=[CH:29][C:3]=1[C:4]([C:6]1[CH:15]=[C:14]2[C:9](=[CH:8][CH:7]=1)[N:10]=[CH:11][C:12]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[N:13]2)=[O:5] | null | US20150158826A1_1074 | 2,015 | CC(C)(C)OC(=O)[N:33]1[CH2:32][CH2:31][N:30]([c:29]2[cH:28][n:27][c:26]3[cH:25][cH:24][c:23]([C:21]([c:20]4[c:18]([F:19])[cH:17][cH:16][c:15]([NH:14][C:2](=[O:1])[NH:3][c:4]5[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]5)[cH:39]4)=[O:22])[cH:38][c:37]3[n:36]2)[CH2:35][CH2:34]1.ClCCl.O=C(O)C(F)(F)F>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1)[NH:14][c:15]1[cH:16][cH:17][c:18]([F:19])[c:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][c:26]3[n:27][cH:28][c:29]([N:30]4[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)[n:36][c:37]3[cH:38]2)[cH:39]1 | 0.244757 | CC(C)(C)OC(=O)N1CCN(c2cnc3ccc(C(=O)c4cc(NC(=O)Nc5cccc(C(F)(F)F)c5)ccc4F)cc3n2)CC1.ClCCl.O=C(O)C(F)(F)F>>O=C(Nc1cccc(C(F)(F)F)c1)Nc1ccc(F)c(C(=O)c2ccc3ncc(N4CCNCC4)nc3c2)c1 | CC(C)(C)OC(=O)N1CCN(c2cnc3ccc(C(=O)c4cc(NC(=O)Nc5cccc(C(F)(F)F)c5)ccc4F)cc3n2)CC1.ClCCl.O=C(O)C(F)(F)F>>O=C(Nc1cccc(C(F)(F)F)c1)Nc1ccc(F)c(C(=O)c2ccc3ncc(N4CCNCC4)nc3c2)c1 | US20150158826A1_1074apps | 7b624c363c3ba344bb12e250c6961efc9413e60cf8da71965c3cdf55 | CC(C)(C)OC(=O)[N:33]1[CH2:32][CH2:31][N:30]([c:29]2[cH:28][n:27][c:26]3[cH:25][cH:24][c:23]([C:21]([c:20]4[c:18]([F:19])[cH:17][cH:16][c:15]([NH:14][C:2](=[O:1])[NH:3][c:4]5[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]5)[cH:39]4)=[O:22])[cH:38][c:37]3[n:36]2)[CH2:35][CH2:34]1.ClCCl.O=C(O)C(F)(F)F | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1)[NH:14][c:15]1[cH:16][cH:17][c:18]([F:19])[c:20]([C:21](=[O:22])[c:23]2[cH:24][cH:25][c:26]3[n:27][cH:28][c:29]([N:30]4[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)[n:36][c:37]3[cH:38]2)[cH:39]1 | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 575 |
304,181 | 988,531 | 1,667,499 | [Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]=O)=[CH:4][CH:3]=1.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.ClCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:4][CH:3]=1 | |f:3.4| | US09133148B2_0721 | 2,015 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O.O=[CH:9][c:8]1[c:2]([CH3:1])[n:3][c:4]([Br:5])[cH:6][cH:7]1.[NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.[Na+]>>[CH3:1][c:2]1[n:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1 | 0.545273 | CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].CC(C)(C)OC(=O)N1CCNCC1.Cc1nc(Br)ccc1C=O.ClCCl.O>>Cc1nc(Br)ccc1CN1CCN(C(=O)OC(C)(C)C)CC1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)(C)OC(=O)N1CCNCC1.Cc1nc(Br)ccc1C=O.ClCCl.O.[Na+]>>Cc1nc(Br)ccc1CN1CCN(C(=O)OC(C)(C)C)CC1 | US09133148B2_0721grants | 27f47996718c5daa8c7b19cb8d34d42a2fa2a8f158a5504fc6346746 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O.O=[CH:9][c:8]1[c:2]([CH3:1])[n:3][c:4]([Br:5])[cH:6][cH:7]1.[NH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.[Na+] | [CH3:1][c:2]1[n:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1 | ([#7;a:4]:[c:3]:[c:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(O=[CH;D2;+0:1]-[c:2]:[c:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | ad8e1685b34ea7ff5cabcb2980537504eae542f2850fd76af8af8fda | 1 | 1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCl.O.[Na+] | 757 |
258,014 | 853,540 | 1,420,087 | [Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:35])=[N:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[CH:23][CH:22]=3)[N:20]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][C:51](Cl)=[O:52])=[CH:46][CH:45]=1)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37].O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([NH:35][C:51](=[O:52])[CH2:50][C:47]3[CH:46]=[CH:45][C:44]([O:43][Si:36]([C:39]([CH3:41])([CH3:40])[CH3:42])([CH3:37])[CH3:38])=[CH:49][CH:48]=3)=[N:17][CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:29])[CH3:30])=[CH:25][CH:26]=3)[N:20]=2)=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2] | null | US08642281B2_0376 | 2,014 | CN(C)c1ccncc1.Cl[C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:52][cH:51]1)=[O:15].O.[NH2:16][c:17]1[n:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]2)[n:35][c:36]1-[c:37]1[cH:38][cH:39][c:40]([O:41][Si:42]([CH3:43])([CH3:44])[C:45]([CH3:46])([CH3:47])[CH3:48])[cH:49][cH:50]1.c1ccncc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14](=[O:15])[NH:16][c:17]2[n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]3)[n:35][c:36]2-[c:37]2[cH:38][cH:39][c:40]([O:41][Si:42]([CH3:43])([CH3:44])[C:45]([CH3:46])([CH3:47])[CH3:48])[cH:49][cH:50]2)[cH:51][cH:52]1 | 0.009853 | CC(C)(C)[Si](C)(C)Oc1ccc(-c2cnc(N)c(-c3ccc(O[Si](C)(C)C(C)(C)C)cc3)n2)cc1.CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Cl)cc1.CN(C)c1ccncc1.O.c1ccncc1>>CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Nc2ncc(-c3ccc(O[Si](C)(C)C(C)(C)C)cc3)nc2-c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1 | CC(C)(C)[Si](C)(C)Oc1ccc(-c2cnc(N)c(-c3ccc(O[Si](C)(C)C(C)(C)C)cc3)n2)cc1.CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Cl)cc1.CN(C)c1ccncc1.O.c1ccncc1>>CC(C)(C)[Si](C)(C)Oc1ccc(CC(=O)Nc2ncc(-c3ccc(O[Si](C)(C)C(C)(C)C)cc3)nc2-c2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1 | US08642281B2_0376grants | cbc2552ce185c0ae45b01862ca3b26885e56cb4a79d73cdbc9e2c786 | CN(C)c1ccncc1.Cl[C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:52][cH:51]1)=[O:15].O.[NH2:16][c:17]1[n:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]2)[n:35][c:36]1-[c:37]1[cH:38][cH:39][c:40]([O:41][Si:42]([CH3:43])([CH3:44])[C:45]([CH3:46])([CH3:47])[CH3:48])[cH:49][cH:50]1.c1ccncc1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14](=[O:15])[NH:16][c:17]2[n:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([O:25][Si:26]([CH3:27])([CH3:28])[C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]3)[n:35][c:36]2-[c:37]2[cH:38][cH:39][c:40]([O:41][Si:42]([CH3:43])([CH3:44])[C:45]([CH3:46])([CH3:47])[CH3:48])[cH:49][cH:50]2)[cH:51][cH:52]1 | ([#7;a:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]):[c:7]:[#7;a:8])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7;a:4]:[c:5](-[NH2;D1;+0:6]):[c:7]:[#7;a:8]) | cb9db0a1cdd21f8e25587d6a44dbb05a31e9e28426dcde5b168d5f64 | 1 | 1 | CN(C)c1ccncc1.O.c1ccncc1 | 399 |
285,636 | 932,723 | 1,563,907 | [Si]([O:8][CH2:9][C:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:30]=[CH:31][C:32](=[O:36])[N:33]([CH3:35])[CH:34]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][CH2:9][C:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:30]=[CH:31][C:32](=[O:36])[N:33]([CH3:35])[CH:34]=5)=[CH:25][CH:24]=4)[CH2:21][CH2:22]3)=[N:18][N:19]=[C:12]2[CH2:11]1 | null | US08927536B2_0575 | 2,015 | CC(C)(C)[Si](C)(C)[O:21][CH2:20][C:18]1([CH3:19])[S:17][CH2:16][CH2:15][n:14]2[c:10]([C:9]3([c:8]4[cH:7][cH:6][c:5](-[c:4]5[cH:3][n:2]([CH3:1])[c:29](=[O:30])[cH:28][cH:27]5)[cH:26][cH:25]4)[CH2:23][CH2:24]3)[n:11][n:12][c:13]2[CH2:22]1.CO.Cl>>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3([c:10]4[n:11][n:12][c:13]5[n:14]4[CH2:15][CH2:16][S:17][C:18]([CH3:19])([CH2:20][OH:21])[CH2:22]5)[CH2:23][CH2:24]3)[cH:25][cH:26]2)[cH:27][cH:28][c:29]1=[O:30] | 0.870236 | CO.Cl.Cn1cc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO[Si](C)(C)C(C)(C)C)C5)CC3)cc2)ccc1=O>>Cn1cc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO)C5)CC3)cc2)ccc1=O | CO.Cl.Cn1cc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO[Si](C)(C)C(C)(C)C)C5)CC3)cc2)ccc1=O>>Cn1cc(-c2ccc(C3(c4nnc5n4CCSC(C)(CO)C5)CC3)cc2)ccc1=O | US08927536B2_0575grants | f044c4de7e4e39211a9ce7730f31375ea72545db9134ed5df55bc836 | CC(C)(C)[Si](C)(C)[O:21][CH2:20][C:18]1([CH3:19])[S:17][CH2:16][CH2:15][n:14]2[c:10]([C:9]3([c:8]4[cH:7][cH:6][c:5](-[c:4]5[cH:3][n:2]([CH3:1])[c:29](=[O:30])[cH:28][cH:27]5)[cH:26][cH:25]4)[CH2:23][CH2:24]3)[n:11][n:12][c:13]2[CH2:22]1.CO.Cl | [CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]3([c:10]4[n:11][n:12][c:13]5[n:14]4[CH2:15][CH2:16][S:17][C:18]([CH3:19])([CH2:20][OH:21])[CH2:22]5)[CH2:23][CH2:24]3)[cH:25][cH:26]2)[cH:27][cH:28][c:29]1=[O:30] | ([C:2]-[OH;D1;+0:1])>>(C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]) | 368b3f927702b41932c1075690d6eeba50254e115711ea09825c0c9c | 1 | 1 | CO.Cl | 708 |
103,971 | 397,470 | 679,577 | [OH:1][C@@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25][NH2:26])=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9].C(N(CC)CC)C.[C:36](O[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>>[OH:1][C@@H:2]([CH3:28])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25][NH:26][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:12][C:11]=2[N:10]([CH3:27])[C:8]1=[O:9] | null | US06878715B1_00256 | 2,005 | CC(C)(C)OC(=O)O[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].CCN(CC)CC.[CH3:1][C@H:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9](=[O:10])[c:11]2[c:12]([n:13][c:14]([CH2:15][NH2:16])[n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32]([CH3:33])[c:34]1=[O:35]>>[CH3:1][C@H:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9](=[O:10])[c:11]2[c:12]([n:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32]([CH3:33])[c:34]1=[O:35] | 0.29722 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.C[C@H](O)CCCCn1c(=O)c2c(nc(CN)n2Cc2ccccc2)n(C)c1=O>>C[C@H](O)CCCCn1c(=O)c2c(nc(CNC(=O)OC(C)(C)C)n2Cc2ccccc2)n(C)c1=O | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.C[C@H](O)CCCCn1c(=O)c2c(nc(CN)n2Cc2ccccc2)n(C)c1=O>>C[C@H](O)CCCCn1c(=O)c2c(nc(CNC(=O)OC(C)(C)C)n2Cc2ccccc2)n(C)c1=O | US06878715B1_00256grants | c5d8f2c566b5dced9997f8030b2c4c5231a3a6b9d376d07abe881e18 | CC(C)(C)OC(=O)O[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].CCN(CC)CC.[CH3:1][C@H:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9](=[O:10])[c:11]2[c:12]([n:13][c:14]([CH2:15][NH2:16])[n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32]([CH3:33])[c:34]1=[O:35] | [CH3:1][C@H:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][n:8]1[c:9](=[O:10])[c:11]2[c:12]([n:13][c:14]([CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24]2[CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32]([CH3:33])[c:34]1=[O:35] | ([C:8]-[NH;D2;+0:9]-[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]-[NH2;D1;+0:9]) | e21cbc5dc2263b0652396beb92f05fda37bb9f2c606e45a3619c49bf | 1 | 1 | CCN(CC)CC | 631 |
365,663 | 690,245 | null | [Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+].[N:35]1C=CC=CC=1>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:35])=[O:5] | |f:2.3| | US20090099184A1_0151 | 2,009 | CC#N.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C([O-])O.O[C:9]([c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:14][c:12]1[Cl:13])=[O:11].[NH4+:10].c1ccncc1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([Cl:13])[cH:14]1 | 0.408836 | CC#N.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CS(=O)(=O)c1ccc(C(=O)O)c(Cl)c1.O=C([O-])O~[NH4+].c1ccncc1>>CS(=O)(=O)c1ccc(C(N)=O)c(Cl)c1 | CC#N.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CS(=O)(=O)c1ccc(C(=O)O)c(Cl)c1.O=C([O-])O.[NH4+].c1ccncc1>>CS(=O)(=O)c1ccc(C(N)=O)c(Cl)c1 | US20090099184A1_0151apps | e2f1f5cead30ee17ee15f7df3b65cd800d8a21a460b5e3f2a4708488 | CC#N.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C([O-])O.O[C:9]([c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:14][c:12]1[Cl:13])=[O:11].[NH4+:10].c1ccncc1 | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([Cl:13])[cH:14]1 | ([NH2;D1;+0:4]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH4+;D0:4]) | c421fff6c68457e5a1b10b45c638efef86b6256b0ea7f128ff2943ad | 1 | 1 | CC#N.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=C([O-])O.c1ccncc1 | 358 |
255,610 | 846,749 | 1,409,214 | [C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=2)[N:25]=[CH:24][N:23]=1.Cl.O1CCOCC1>CCOC(C)=O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:22]3[C:31]4[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=4)[N:25]=[CH:24][N:23]=3)[CH:15]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3] | null | US08618289B2_0806 | 2,013 | C1COCCO1.CCOC(C)=O.Cl.Cl[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:31]2[n:30][cH:29][n:28]1.[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[NH:17][c:18]2[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[o:25][n:26]2)[cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([O:8][c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[NH:17][c:18]4[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[o:25][n:26]4)[cH:27]3)[n:28][cH:29][n:30][c:31]2[cH:32]1 | 0.429105 | C1COCCO1.CC(C)(C)c1cc(NC(=O)Nc2cccc(O)c2)no1.CCOC(C)=O.COc1ccc2c(Cl)ncnc2c1.Cl>>COc1ccc2c(Oc3cccc(NC(=O)Nc4cc(C(C)(C)C)on4)c3)ncnc2c1 | C1COCCO1.CC(C)(C)c1cc(NC(=O)Nc2cccc(O)c2)no1.CCOC(C)=O.COc1ccc2c(Cl)ncnc2c1.Cl>>COc1ccc2c(Oc3cccc(NC(=O)Nc4cc(C(C)(C)C)on4)c3)ncnc2c1 | US08618289B2_0806grants | 32f89a5a132b23fdc110759cbc4a34d7f71e38d7df5552574977bf56 | C1COCCO1.CCOC(C)=O.Cl.Cl[c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][c:31]2[n:30][cH:29][n:28]1.[OH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[NH:17][c:18]2[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[o:25][n:26]2)[cH:27]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([O:8][c:9]3[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[NH:17][c:18]4[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[o:25][n:26]4)[cH:27]3)[n:28][cH:29][n:30][c:31]2[cH:32]1 | ([c:8]-[O;H0;D2;+0:7]-[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).([OH;D1;+0:7]-[c:8]) | 040e0ed2e2cb4b0b62ba03ad3cfe1c87063db3df80ae4aba792d8767 | 1 | 1 | C1COCCO1.CCOC(C)=O.Cl | 668 |
155,047 | 551,381 | 922,316 | [CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[S:21][C:20]3[CH:22]=[C:23]([C:26](O)=[O:27])[CH:24]=[CH:25][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].C(Cl)CCl.Cl.[CH3:38][NH:39][CH3:40]>>[CH3:38][N:39]([CH3:40])[C:26]([C:23]1[CH:24]=[CH:25][C:19]2[CH:18]=[C:17]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:30])[C:2]([CH3:32])([CH3:31])[CH3:1])=[C:7]([CH3:29])[CH:8]=3)([CH2:15][CH3:16])[CH2:13][CH3:14])[S:21][C:20]=2[CH:22]=1)=[O:27] | |f:2.3| | US07582775B2_2417 | 2,009 | Cl.ClCCCl.O[C:27]([c:26]1[cH:25][cH:24][c:23]2[cH:22][c:21]([C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[c:6]3[cH:7][cH:8][c:9]([O:10][CH2:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[cH:20]3)[s:34][c:33]2[cH:32]1)=[O:28].[NH:29]([CH3:30])[CH3:31]>>[CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[cH:20]1)[c:21]1[cH:22][c:23]2[cH:24][cH:25][c:26]([C:27](=[O:28])[N:29]([CH3:30])[CH3:31])[cH:32][c:33]2[s:34]1 | 0.301984 | CCC(CC)(c1ccc(OCC(=O)C(C)(C)C)c(C)c1)c1cc2ccc(C(=O)O)cc2s1.CNC~Cl.ClCCCl>>CCC(CC)(c1ccc(OCC(=O)C(C)(C)C)c(C)c1)c1cc2ccc(C(=O)N(C)C)cc2s1 | CCC(CC)(c1ccc(OCC(=O)C(C)(C)C)c(C)c1)c1cc2ccc(C(=O)O)cc2s1.CNC.Cl.ClCCCl>>CCC(CC)(c1ccc(OCC(=O)C(C)(C)C)c(C)c1)c1cc2ccc(C(=O)N(C)C)cc2s1 | US07582775B2_2417grants | 245202f0c26ca0c1abd03271b2556ca10ecebc71d114a0b650d242be | Cl.ClCCCl.O[C:27]([c:26]1[cH:25][cH:24][c:23]2[cH:22][c:21]([C:3]([CH2:2][CH3:1])([CH2:4][CH3:5])[c:6]3[cH:7][cH:8][c:9]([O:10][CH2:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[cH:20]3)[s:34][c:33]2[cH:32]1)=[O:28].[NH:29]([CH3:30])[CH3:31] | [CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[c:18]([CH3:19])[cH:20]1)[c:21]1[cH:22][c:23]2[cH:24][cH:25][c:26]([C:27](=[O:28])[N:29]([CH3:30])[CH3:31])[cH:32][c:33]2[s:34]1 | ([C;D1;H3:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | 11438d3fa968bbd8c4f3372ffee303c561281eed4a1be36b1ce3c5b0 | 1 | 1 | Cl.ClCCCl | 44 |
197,764 | 676,943 | 1,118,143 | [F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1)[N:10]([CH3:26])[N:9]=[CH:8]2>[Pd].C1COCC1>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:13]=2[C:14]2[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH:18]=2)[N:10]([CH3:26])[N:9]=[CH:8]3)=[C:2]([F:1])[CH:30]=1 | null | US08030302B2_0134 | 2,011 | C1CCOC1.O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][c:7]2[cH:6][c:5]3[cH:4][n:3][n:2]([CH3:1])[c:31]3[cH:30][c:17]2-[c:18]2[cH:19][n:20][n:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29]2)[c:15]([F:16])[cH:14]1.[Pd]>>[CH3:1][n:2]1[n:3][cH:4][c:5]2[cH:6][c:7]([O:8][c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]3[F:16])[c:17](-[c:18]3[cH:19][n:20][n:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29]3)[cH:30][c:31]12 | 0.403641 | C1CCOC1.Cn1ncc2cc(Oc3ccc([N+](=O)[O-])cc3F)c(-c3cnn(C(=O)OC(C)(C)C)c3)cc21.[Pd]>>Cn1ncc2cc(Oc3ccc(N)cc3F)c(-c3cnn(C(=O)OC(C)(C)C)c3)cc21 | C1CCOC1.Cn1ncc2cc(Oc3ccc([N+](=O)[O-])cc3F)c(-c3cnn(C(=O)OC(C)(C)C)c3)cc21.[Pd]>>Cn1ncc2cc(Oc3ccc(N)cc3F)c(-c3cnn(C(=O)OC(C)(C)C)c3)cc21 | US08030302B2_0134grants | 784f734018edd56960e65b126c0c721613a07aea5614331f2745c06a | C1CCOC1.O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][c:7]2[cH:6][c:5]3[cH:4][n:3][n:2]([CH3:1])[c:31]3[cH:30][c:17]2-[c:18]2[cH:19][n:20][n:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29]2)[c:15]([F:16])[cH:14]1.[Pd] | [CH3:1][n:2]1[n:3][cH:4][c:5]2[cH:6][c:7]([O:8][c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]3[F:16])[c:17](-[c:18]3[cH:19][n:20][n:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29]3)[cH:30][c:31]12 | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[#8:6]-[c:7]):[c:8]:[c:9]:1) | 29ce6f8549b3eb39f0ff459e6dcee2e695f06f6055034d715c31e38e | 1 | 1 | C1CCOC1.[Pd] | 335 |
68,240 | 284,067 | 481,566 | [CH3:1][O:2][CH2:3][C@@H:4]([NH:6][C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:15])[CH3:5].[Cl:16][CH2:17][C:18](Cl)=[O:19]>>[Cl:16][CH2:17][C:18]([N:6]([C:7]1[C:12]([CH2:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:15])[C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])=[O:19] | null | US06107521_ | 2,000 | Cl[C:11](=[O:12])[CH2:13][Cl:14].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[NH:10][C@@H:15]([CH3:16])[CH2:17][O:18][CH3:19]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[N:10]([C:11](=[O:12])[CH2:13][Cl:14])[C@@H:15]([CH3:16])[CH2:17][O:18][CH3:19] | 0.987988 | CCc1cccc(C)c1N[C@@H](C)COC.O=C(Cl)CCl>>CCc1cccc(C)c1N(C(=O)CCl)[C@@H](C)COC | CCc1cccc(C)c1N[C@@H](C)COC.O=C(Cl)CCl>>CCc1cccc(C)c1N(C(=O)CCl)[C@@H](C)COC | US06107521_grants | b887e21020c6740d4079778f65eda2f787f3ef895d58d92f06ac9c62 | Cl[C:11](=[O:12])[CH2:13][Cl:14].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[NH:10][C@@H:15]([CH3:16])[CH2:17][O:18][CH3:19] | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[c:9]1[N:10]([C:11](=[O:12])[CH2:13][Cl:14])[C@@H:15]([CH3:16])[CH2:17][O:18][CH3:19] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[c:6])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[c:6]) | 243d4d70ed956e3ba4e5bc0d489e1112d3a0eba27892f1d71f3a13af | 1 | 1 | null | 160 |
360,239 | 624,723 | null | C([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[CH:24]=[C:23]([N:25]2[C:33]3[CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30][C:29](=[O:36])[C:28]=3[C:27]([CH3:37])=[N:26]2)[CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19])C1C=CC=CC=1>CO.[Pd]>[OH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[CH:24]=[C:23]([N:25]2[C:33]3[CH2:32][C:31]([CH3:34])([CH3:35])[CH2:30][C:29](=[O:36])[C:28]=3[C:27]([CH3:37])=[N:26]2)[CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19] | null | US20080269193A1_0601 | 2,008 | CO.[Pd].c1ccc(C[O:20][C@@H:19]2[C@@H:14]([NH:13][c:12]3[c:8]([C:9]([NH2:10])=[O:11])[cH:7][cH:6][c:5](-[n:4]4[n:3][c:2]([CH3:1])[c:23]5[c:22]4[CH2:30][C:27]([CH3:28])([CH3:29])[CH2:26][C:24]5=[O:25])[cH:21]3)[CH2:15][CH2:16][CH2:17][CH2:18]2)cc1>>[CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([NH:13][C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]3[OH:20])[cH:21]2)[c:22]2[c:23]1[C:24](=[O:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2 | 0.743862 | CO.Cc1nn(-c2ccc(C(N)=O)c(N[C@H]3CCCC[C@@H]3OCc3ccccc3)c2)c2c1C(=O)CC(C)(C)C2.[Pd]>>Cc1nn(-c2ccc(C(N)=O)c(N[C@H]3CCCC[C@@H]3O)c2)c2c1C(=O)CC(C)(C)C2 | CO.Cc1nn(-c2ccc(C(N)=O)c(N[C@H]3CCCC[C@@H]3OCc3ccccc3)c2)c2c1C(=O)CC(C)(C)C2.[Pd]>>Cc1nn(-c2ccc(C(N)=O)c(N[C@H]3CCCC[C@@H]3O)c2)c2c1C(=O)CC(C)(C)C2 | US20080269193A1_0601apps | 72047cc04da5c0fbf4bb21d76f226cb700a1701d1bb04ebb68988bb4 | CO.[Pd].c1ccc(C[O:20][C@@H:19]2[C@@H:14]([NH:13][c:12]3[c:8]([C:9]([NH2:10])=[O:11])[cH:7][cH:6][c:5](-[n:4]4[n:3][c:2]([CH3:1])[c:23]5[c:22]4[CH2:30][C:27]([CH3:28])([CH3:29])[CH2:26][C:24]5=[O:25])[cH:21]3)[CH2:15][CH2:16][CH2:17][CH2:18]2)cc1 | [CH3:1][c:2]1[n:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([NH2:10])=[O:11])[c:12]([NH:13][C@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]3[OH:20])[cH:21]2)[c:22]2[c:23]1[C:24](=[O:25])[CH2:26][C:27]([CH3:28])([CH3:29])[CH2:30]2 | ([C:1]-[OH;D1;+0:2])>>([C:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | b09baddfd5988158c3a819435de5f508e6fb5e1babae0fd337ba07ac | 1 | 1 | CO.[Pd] | 178 |
418,957 | 1,748,987 | null | [CH3:1][C:2]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]2[CH2:19][CH2:18][CH2:17][O:16]2)[C:3]=1[O:4][CH2:5][C:6](OC)=[O:7].[NH2:20][NH2:21]>CCO>[CH3:1][C:2]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]2[CH2:19][CH2:18][CH2:17][O:16]2)[C:3]=1[O:4][CH2:5][C:6]([NH:20][NH2:21])=[O:7] | null | US20150252030A1_0441 | 2,015 | CCO.CO[C:9]([CH2:8][O:7][c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:19][c:13]1[CH:14]1[CH2:15][CH2:16][CH2:17][O:18]1)=[O:10].[NH2:11][NH2:12]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([O:7][CH2:8][C:9](=[O:10])[NH:11][NH2:12])[c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][O:18]2)[cH:19]1 | 0.746296 | CCO.COC(=O)COc1c(C)cc(C)cc1C1CCCO1.NN>>Cc1cc(C)c(OCC(=O)NN)c(C2CCCO2)c1 | CCO.COC(=O)COc1c(C)cc(C)cc1C1CCCO1.NN>>Cc1cc(C)c(OCC(=O)NN)c(C2CCCO2)c1 | US20150252030A1_0441apps | 51cb6d95315e942116d885075f310b96905767d53c176e76f063601f | CCO.CO[C:9]([CH2:8][O:7][c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:19][c:13]1[CH:14]1[CH2:15][CH2:16][CH2:17][O:18]1)=[O:10].[NH2:11][NH2:12] | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([O:7][CH2:8][C:9](=[O:10])[NH:11][NH2:12])[c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][O:18]2)[cH:19]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[N;D1;H2:4])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([N;D1;H2:4]-[NH2;D1;+0:5]) | 4a4cc8c8415e11cba150e15e821b1c18f8effbaac08580c6d66871d8 | 1 | 1 | CCO | 130 |
1,020 | 5,301 | 5,982 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]1([CH:18]2[CH2:24][C:23](=O)[NH:22][C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[S:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:12]1([CH:18]2[CH2:24][CH2:23][NH:22][C:21]3[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=3[S:19]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1 | |f:0.1.2.3.4.5,8.9| | US03953469_ | 1,976 | C1CCOC1.O.O=[C:7]1[CH2:6][CH:5]([c:4]2[cH:3][cH:2][cH:1][cH:17][cH:16]2)[S:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[NH:8]1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-]>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][NH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[S:15]2)[cH:16][cH:17]1 | 0.753983 | C1CCOC1.O.O=C1CC(c2ccccc2)Sc2ccccc2N1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+].[Na+]~[OH-]>>c1ccc(C2CCNc3ccccc3S2)cc1 | C1CCOC1.O.O=C1CC(c2ccccc2)Sc2ccccc2N1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-]>>c1ccc(C2CCNc3ccccc3S2)cc1 | US03953469_grants | da3404629531551265d1dce0c1d2ec8c623871f86c0800cee74c8eb8 | C1CCOC1.O.O=[C:7]1[CH2:6][CH:5]([c:4]2[cH:3][cH:2][cH:1][cH:17][cH:16]2)[S:15][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[NH:8]1.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-] | [cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][NH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[S:15]2)[cH:16][cH:17]1 | ([#7:2]-[CH2;D2;+0:1]-[C:3])>>(O=[C;H0;D3;+0:1](-[#7:2])-[C:3]) | 164bcd5926595fb14a6a9bdfa6263711f1e81657ce47f1a9ea439ccb | 1 | 1 | C1CCOC1.O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+].[OH-] | 112 |
408,983 | 1,602,923 | null | C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[CH:20]=[C:21]4[C:36]([CH3:38])([CH3:37])[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:22]4=[CH:23][C:24]=3[C:25]([CH3:29])([CH3:28])[C:26]=2[CH:27]=1.[CH3:39][C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[C:41]=1[NH2:48].CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:37][C:36]1([CH3:38])[C:21]2[C:22](=[CH:23][C:24]3[C:25]([CH3:29])([CH3:28])[C:26]4[CH:27]=[C:15]([NH:48][C:41]5[C:42]([CH3:47])=[CH:43][C:44]([CH3:46])=[CH:45][C:40]=5[CH3:39])[CH:16]=[CH:17][C:18]=4[C:19]=3[CH:20]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2 | |f:3.4,5.6.7| | US20140316134A1_0146 | 2,014 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[c:17]1[cH:18][c:19]3[c:20]([cH:21][c:22]1-2)[C:23]([CH3:24])([CH3:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1-3.CC(=O)[O-].CC(=O)[O-].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].Cc1ccccc1.O.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH2:7])[c:32]([CH3:33])[cH:34]1.[Na+].[Pd+2]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]([CH3:15])([CH3:16])[c:17]2[cH:18][c:19]4[c:20]([cH:21][c:22]2-3)[C:23]([CH3:24])([CH3:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2-4)[c:32]([CH3:33])[cH:34]1 | 0.380118 | CC(=O)[O-]~CC(=O)[O-]~[Pd+2].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-]~[Na+].CC1(C)c2ccccc2-c2cc3c(cc21)-c1ccc(Br)cc1C3(C)C.Cc1cc(C)c(N)c(C)c1.Cc1ccccc1.O>>Cc1cc(C)c(Nc2ccc3c(c2)C(C)(C)c2cc4c(cc2-3)C(C)(C)c2ccccc2-4)c(C)c1 | CC(=O)[O-].CC(=O)[O-].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].CC1(C)c2ccccc2-c2cc3c(cc21)-c1ccc(Br)cc1C3(C)C.Cc1cc(C)c(N)c(C)c1.Cc1ccccc1.O.[Na+].[Pd+2]>>Cc1cc(C)c(Nc2ccc3c(c2)C(C)(C)c2cc4c(cc2-3)C(C)(C)c2ccccc2-4)c(C)c1 | US20140316134A1_0146apps | a46b41a52b8f035559913c64eaf670ea481614fca21aa7c23aeb84f4 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[c:17]1[cH:18][c:19]3[c:20]([cH:21][c:22]1-2)[C:23]([CH3:24])([CH3:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1-3.CC(=O)[O-].CC(=O)[O-].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].Cc1ccccc1.O.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH2:7])[c:32]([CH3:33])[cH:34]1.[Na+].[Pd+2] | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([NH:7][c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[C:14]([CH3:15])([CH3:16])[c:17]2[cH:18][c:19]4[c:20]([cH:21][c:22]2-3)[C:23]([CH3:24])([CH3:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2-4)[c:32]([CH3:33])[cH:34]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[NH;D2;+0:4]-[c:5])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([NH2;D1;+0:4]-[c:5]) | c4f108b12719c39b2aa28b4489e5c7c15d1240c9e8fd5aefb447933a | 0.5 | 2 | CC(=O)[O-].CC(=O)[O-].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].Cc1ccccc1.O.[Na+].[Pd+2] | 405 |
225,545 | 756,119 | 1,245,980 | C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[N:19][CH:20]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([C:15]1[CH:20]=[N:19][CH:18]=[C:17]([CH:16]=1)[CH:21]=[O:22])([CH3:14])([CH3:12])[CH3:13] | null | US08299267B2_0690 | 2,012 | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][c:9]([CH2:10][OH:11])[cH:12]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][c:9]([CH:10]=[O:11])[cH:12]1 | 0.552446 | CC(C)(C)c1cncc(CO)c1.CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CC(C)(C)c1cncc(C=O)c1 | CC(C)(C)c1cncc(CO)c1.CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CC(C)(C)c1cncc(C=O)c1 | US08299267B2_0690grants | 8be9d11262cacd68d43c2ac65fc9cdf5938598e453b5048227b355fe | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][c:9]([CH2:10][OH:11])[cH:12]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][cH:8][c:9]([CH:10]=[O:11])[cH:12]1 | ([#7;a:1]:[c:2]:[c:3]-[CH;D2;+0:4]=[O;H0;D1;+0:5])>>([#7;a:1]:[c:2]:[c:3]-[CH2;D2;+0:4]-[OH;D1;+0:5]) | cfe281a75d1b2b2acde2ac44b3a8433d97f5dddc83d112a905a74a4c | 1 | 1 | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl | 520 |
163,954 | 577,444 | 961,573 | [CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[Cl:13][C:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[N:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][N:17]1[CH:18]=[C:14]([Cl:13])[C:15]([C:19]([F:22])([F:21])[F:20])=[N:16]1 | |f:2.3.4| | US07674807B2_0509 | 2,010 | CCOC(C)=O.CN(C)C=O.Cl[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:18]([N+:19](=[O:20])[O-:21])[cH:17][cH:16]1.O=C([O-])[O-].[K+].[K+].[nH:6]1[cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[n:15]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][n:6]2[cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[n:15]2)[cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21] | 0.246774 | CCOC(C)=O.CN(C)C=O.Cc1cc(CCl)ccc1[N+](=O)[O-].FC(F)(F)c1n[nH]cc1Cl.O=C([O-])[O-]~[K+]~[K+]>>Cc1cc(Cn2cc(Cl)c(C(F)(F)F)n2)ccc1[N+](=O)[O-] | CCOC(C)=O.CN(C)C=O.Cc1cc(CCl)ccc1[N+](=O)[O-].FC(F)(F)c1n[nH]cc1Cl.O=C([O-])[O-].[K+].[K+]>>Cc1cc(Cn2cc(Cl)c(C(F)(F)F)n2)ccc1[N+](=O)[O-] | US07674807B2_0509grants | a7ac03163b9365a3c2d2eced6ed067b9b0250b4f0f0a1a0d81708338 | CCOC(C)=O.CN(C)C=O.Cl[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:18]([N+:19](=[O:20])[O-:21])[cH:17][cH:16]1.O=C([O-])[O-].[K+].[K+].[nH:6]1[cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[n:15]1 | [CH3:1][c:2]1[cH:3][c:4]([CH2:5][n:6]2[cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[n:15]2)[cH:16][cH:17][c:18]1[N+:19](=[O:20])[O-:21] | ([#7;a:3]:[n;H0;D3;+0:4](:[c:5])-[CH2;D2;+0:1]-[c:2])>>(Cl-[CH2;D2;+0:1]-[c:2]).([#7;a:3]:[nH;D2;+0:4]:[c:5]) | a760a5bd8c67d2961dcc9e72b4802d315357aa2b870b0c35a7da3fc8 | 1 | 1 | CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 842 |
347,635 | 434,069 | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:14])[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:6][CH:7]=1 | |f:1.2.3.4.5.6,7.8| | US20070043104A1_0267 | 2,007 | C1CCOC1.O=C([O-])O.[Al+3].[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.[H-].[H-].[H-].[H-].[Li+].[Na+]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]([OH:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | 0.855738 | C1CCOC1.CN(C)CCC(=O)c1ccc(Cl)cc1.O=C([O-])O~[Na+].[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>CN(C)CCC(O)c1ccc(Cl)cc1 | C1CCOC1.CN(C)CCC(=O)c1ccc(Cl)cc1.O=C([O-])O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+]>>CN(C)CCC(O)c1ccc(Cl)cc1 | US20070043104A1_0267apps | 6af109aacc93adc116eb07a79c574a7fdf3b7f3f68c36478ee6af64a | C1CCOC1.O=C([O-])O.[Al+3].[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.[H-].[H-].[H-].[H-].[Li+].[Na+] | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]([OH:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | ([C:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4])>>([C:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]) | e79b9f0e956cb38254670cbba4f53d0c22148efe9b15465e130440fe | 1 | 1 | C1CCOC1.O=C([O-])O.[Al+3].[H-].[H-].[H-].[H-].[Li+].[Na+] | 24 |
118,166 | 440,595 | 749,407 | [CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[C:9]([Cl:20])[S:8][C:7]=1[NH:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])=[O:5])[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[C:9]([Cl:20])[S:8][C:7]=1[NH:21][C:22](=[O:26])[CH2:23][C:24]#[N:25])=[O:5])[CH3:2] | |f:1.2| | US07119205B2_0669 | 2,006 | CCO.O.O=[N+:22]([O-])[c:21]1[cH:20][cH:19][c:18](-[c:17]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]#[N:13])[s:14][c:15]2[Cl:16])[cH:24][cH:23]1.[Cl-].[Fe].[NH4+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]#[N:13])[s:14][c:15]([Cl:16])[c:17]1-[c:18]1[cH:19][cH:20][c:21]([NH2:22])[cH:23][cH:24]1 | 0.958204 | CCO.CCOC(=O)c1c(NC(=O)CC#N)sc(Cl)c1-c1ccc([N+](=O)[O-])cc1.O.[Cl-]~[NH4+].[Fe]>>CCOC(=O)c1c(NC(=O)CC#N)sc(Cl)c1-c1ccc(N)cc1 | CCO.CCOC(=O)c1c(NC(=O)CC#N)sc(Cl)c1-c1ccc([N+](=O)[O-])cc1.O.[Cl-].[Fe].[NH4+]>>CCOC(=O)c1c(NC(=O)CC#N)sc(Cl)c1-c1ccc(N)cc1 | US07119205B2_0669grants | bfb8f2b20f5a762d1142fea6f9e4887e0865895d6920169129bfd290 | CCO.O.O=[N+:22]([O-])[c:21]1[cH:20][cH:19][c:18](-[c:17]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]#[N:13])[s:14][c:15]2[Cl:16])[cH:24][cH:23]1.[Cl-].[Fe].[NH4+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][C:9](=[O:10])[CH2:11][C:12]#[N:13])[s:14][c:15]([Cl:16])[c:17]1-[c:18]1[cH:19][cH:20][c:21]([NH2:22])[cH:23][cH:24]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.O.[Cl-].[Fe].[NH4+] | 1 |
114,689 | 429,682 | 732,485 | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][CH2:17][CH2:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)=[O:20]>>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][C:19]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23][CH2:22]2)=[O:20])[CH2:11][CH2:10]1 | |f:0.1| | US07074796B2_0152 | 2,006 | Cl.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.[NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2:18]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2:18]1)[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21 | 0.873413 | Cl~Clc1ccccc1N1CCNCC1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2ccccc2Cl)CC1)N1CCc2ccccc21 | Cl.Clc1ccccc1N1CCNCC1.O=C(CCCCl)N1CCc2ccccc21>>O=C(CCCN1CCN(c2ccccc2Cl)CC1)N1CCc2ccccc21 | US07074796B2_0152grants | b8f98aaf2ee7897fa1d8c0856cd9561a0a7b913c2ef374f1908d2b7c | Cl.Cl[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21.[NH:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2:18]1 | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[CH2:17][CH2:18]1)[N:19]1[CH2:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]21 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(Cl-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | c38df6bb72f417e54d2346e687e032ed86554f208af48effa9422912 | 0.5 | 2 | Cl | 138 |
347,950 | 440,937 | null | C(N(CC)C(C)C)(C)C.[N+:10]([C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].Cl[CH2:21][O:22][CH3:23]>ClCCl>[CH3:21][O:22][CH2:23][O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1 | null | US20070060607A1_0803 | 2,007 | CCN(C(C)C)C(C)C.ClCCl.Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | 0.965379 | CCN(C(C)C)C(C)C.COCCl.ClCCl.O=[N+]([O-])c1cccc(O)c1>>COCOc1cccc([N+](=O)[O-])c1 | CCN(C(C)C)C(C)C.COCCl.ClCCl.O=[N+]([O-])c1cccc(O)c1>>COCOc1cccc([N+](=O)[O-])c1 | US20070060607A1_0803apps | fbfece8eac3d20db59e4ccf8df8e269943f1ab1ea4c6b1e511e8d542 | CCN(C(C)C)C(C)C.ClCCl.Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | ([#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Cl-[CH2;D2;+0:1]-[#8:2]).([OH;D1;+0:3]-[c:4]) | fc6fab65fb339dbd7dfcd04c121911749ca2392ca0b8fedb59c018a1 | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 375 |
143,195 | 514,691 | 862,232 | CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:29])[CH:20]=[C:21]([F:22])[C:15]=3[O:14]2)(=O)=O)=CC=1.[CH3:30][NH2:31]>>[F:22][C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH:31][CH3:30])[CH2:17][C:16]=2[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:20]=1 | null | US07435837B2_1472 | 2,008 | Cc1ccc(S(=O)(=O)O[CH2:3][CH:4]2[CH2:5][c:6]3[cH:7][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[Cl:15])[cH:16][c:17]([F:18])[c:19]3[O:20]2)cc1.[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][CH:4]1[CH2:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[Cl:15])[cH:16][c:17]([F:18])[c:19]2[O:20]1 | 0.991743 | CN.Cc1ccc(S(=O)(=O)OCC2Cc3cc(-c4ccccc4Cl)cc(F)c3O2)cc1>>CNCC1Cc2cc(-c3ccccc3Cl)cc(F)c2O1 | CN.Cc1ccc(S(=O)(=O)OCC2Cc3cc(-c4ccccc4Cl)cc(F)c3O2)cc1>>CNCC1Cc2cc(-c3ccccc3Cl)cc(F)c2O1 | US07435837B2_1472grants | 0b0b1f02b67b4865a3362464b6549d133d1d64e302e1c44f8d1f8832 | Cc1ccc(S(=O)(=O)O[CH2:3][CH:4]2[CH2:5][c:6]3[cH:7][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[Cl:15])[cH:16][c:17]([F:18])[c:19]3[O:20]2)cc1.[CH3:1][NH2:2] | [CH3:1][NH:2][CH2:3][CH:4]1[CH2:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[Cl:15])[cH:16][c:17]([F:18])[c:19]2[O:20]1 | ([#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4])>>(C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#8:3]):c:c:1).([C;D1;H3:4]-[NH2;D1;+0:5]) | 70f9819301f99f8fb836528f3cc2016a5d4556185871b73f3dd414d2 | 1 | 1 | null | 853 |
438,392 | 1,896,668 | null | [NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C1COCC1.CCOC(C)=O>[Cl:21][CH2:22][C:23]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:24] | null | US20160176916A1_0702 | 2,016 | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.Cl[C:12](=[O:13])[CH2:14][Cl:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH2:14][Cl:15] | 0.401135 | C1CCOC1.CC(C)(C)OC(=O)NCCN.CCN(C(C)C)C(C)C.CCOC(C)=O.O=C(Cl)CCl>>CC(C)(C)OC(=O)NCCNC(=O)CCl | C1CCOC1.CC(C)(C)OC(=O)NCCN.CCN(C(C)C)C(C)C.CCOC(C)=O.O=C(Cl)CCl>>CC(C)(C)OC(=O)NCCNC(=O)CCl | US20160176916A1_0702apps | a01eeb9834c4e2c6eb69bc525187b4f671509b631a208d62ed3a9964 | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.Cl[C:12](=[O:13])[CH2:14][Cl:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH2:14][Cl:15] | ([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 | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O | 45 |
302,993 | 985,354 | 1,661,612 | [CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:3][CH2:2]1 | |f:1.2.3| | US09120777B2_0419 | 2,015 | Cc1ccccc1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[c:16]([CH:17]2[CH2:18][CH2:19]2)[cH:20][c:21]1[CH2:22][OH:23].[Mn+4].[O-2].[O-2]>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[c:16]([CH:17]2[CH2:18][CH2:19]2)[cH:20][c:21]1[CH:22]=[O:23] | 0.818846 | CC(C)Oc1cc(-c2ccc(F)cc2F)c(C2CC2)cc1CO.Cc1ccccc1.[Mn+4]~[O-2]~[O-2]>>CC(C)Oc1cc(-c2ccc(F)cc2F)c(C2CC2)cc1C=O | CC(C)Oc1cc(-c2ccc(F)cc2F)c(C2CC2)cc1CO.Cc1ccccc1.[Mn+4].[O-2].[O-2]>>CC(C)Oc1cc(-c2ccc(F)cc2F)c(C2CC2)cc1C=O | US09120777B2_0419grants | 1b1b15e69959a1f64a09e2e83f20d16b41cd4f44b9124d4403ecf59e | Cc1ccccc1.[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[c:16]([CH:17]2[CH2:18][CH2:19]2)[cH:20][c:21]1[CH2:22][OH:23].[Mn+4].[O-2].[O-2] | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[c:16]([CH:17]2[CH2:18][CH2:19]2)[cH:20][c:21]1[CH:22]=[O:23] | ([O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3])>>([OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]) | 6f544a9b286c4786b46429a74b4a72e536e22ba10273cfcd1d3d737e | 1 | 1 | Cc1ccccc1.[Mn+4].[O-2].[O-2] | 179 |
341,025 | 324,771 | null | [CH2:1]([C:3]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH2:29]([O:31][C:32](=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br)[CH3:30]>>[CH2:29]([O:31][C:32](=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:3]([CH2:4][CH3:5])([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]([CH2:15][CH3:16])([OH:17])[CH2:18][CH3:19])=[C:8]([CH3:20])[CH:7]=2)[CH2:1][CH3:2])=[CH:22][C:23]=1[CH3:28])[CH3:30] | null | US20060025474A1_1214 | 2,006 | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:11][c:12]1[cH:13][cH:14][c:15]([C:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[c:21]2[cH:22][cH:23][c:24]([C:25]#[C:26][C:27]([OH:28])([CH2:29][CH3:30])[CH2:31][CH3:32])[c:33]([CH3:34])[cH:35]2)[cH:36][c:37]1[CH3:38]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([C:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[c:21]2[cH:22][cH:23][c:24]([C:25]#[C:26][C:27]([OH:28])([CH2:29][CH3:30])[CH2:31][CH3:32])[c:33]([CH3:34])[cH:35]2)[cH:36][c:37]1[CH3:38] | 0.526856 | CCC(O)(C#Cc1ccc(C(CC)(CC)c2ccc(O)c(C)c2)cc1C)CC.CCOC(=O)CCCCCBr>>CCOC(=O)CCCCCOc1ccc(C(CC)(CC)c2ccc(C#CC(O)(CC)CC)c(C)c2)cc1C | CCC(O)(C#Cc1ccc(C(CC)(CC)c2ccc(O)c(C)c2)cc1C)CC.CCOC(=O)CCCCCBr>>CCOC(=O)CCCCCOc1ccc(C(CC)(CC)c2ccc(C#CC(O)(CC)CC)c(C)c2)cc1C | US20060025474A1_1214apps | c151e8291e335e44b9ba9492b1ca27c1d0094105a2d8259a6bae06d3 | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:11][c:12]1[cH:13][cH:14][c:15]([C:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[c:21]2[cH:22][cH:23][c:24]([C:25]#[C:26][C:27]([OH:28])([CH2:29][CH3:30])[CH2:31][CH3:32])[c:33]([CH3:34])[cH:35]2)[cH:36][c:37]1[CH3:38] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([C:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[c:21]2[cH:22][cH:23][c:24]([C:25]#[C:26][C:27]([OH:28])([CH2:29][CH3:30])[CH2:31][CH3:32])[c:33]([CH3:34])[cH:35]2)[cH:36][c:37]1[CH3:38] | ([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 | null | 75 |
215,651 | 726,048 | 1,196,096 | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10] | null | US08188113B2_0541 | 2,012 | O=S(=O)(O)O.O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:11][cH:12][c:13]1[Cl:14]>>[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Cl:14] | 0.807284 | O=C(O)Cc1ccccc1Cl.O=S(=O)(O)O.O=[N+]([O-])O>>O=C(O)Cc1cc([N+](=O)[O-])ccc1Cl | O=C(O)Cc1ccccc1Cl.O=S(=O)(O)O.O=[N+]([O-])O>>O=C(O)Cc1cc([N+](=O)[O-])ccc1Cl | US08188113B2_0541grants | 4101b47ac662db6e71c1e6f2e3cbf52fb6c036deb2a5d7539f69a16f | O=S(=O)(O)O.O[N+:8](=[O:9])[O-:10].[O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][cH:7][cH:11][cH:12][c:13]1[Cl:14] | [O:1]=[C:2]([OH:3])[CH2:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12][c:13]1[Cl:14] | ([O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]).([c:4]:[cH;D2;+0:5]:[c:6]) | c25d51e5af868cef93abbb502e1d42ba1564ccc8abe5e0e442b85ea3 | 1 | 1 | O=S(=O)(O)O | 21 |
262,092 | 864,518 | 1,439,544 | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][NH2:30])[CH2:24][CH2:23]1>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:30][CH2:29][CH2:28][N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18] | null | US08680139B2_0219 | 2,014 | O[C:9](=[O:10])[c:11]1[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([S:18][c:19]2[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]2[Cl:26])[s:27]1.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][NH2:8])[CH2:28][CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([S:18][c:19]3[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]3[Cl:26])[s:27]2)[CH2:28][CH2:29]1 | 0.711421 | CN1CCN(CCN)CC1.O=C(O)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1>>CN1CCN(CCNC(=O)c2cc([N+](=O)[O-])c(Sc3c(Cl)cncc3Cl)s2)CC1 | CN1CCN(CCN)CC1.O=C(O)c1cc([N+](=O)[O-])c(Sc2c(Cl)cncc2Cl)s1>>CN1CCN(CCNC(=O)c2cc([N+](=O)[O-])c(Sc3c(Cl)cncc3Cl)s2)CC1 | US08680139B2_0219grants | ece701fc04ee2cb06ad53184c274d673243a5fb4f3b577eb6762c980 | O[C:9](=[O:10])[c:11]1[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([S:18][c:19]2[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]2[Cl:26])[s:27]1.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][NH2:8])[CH2:28][CH2:29]1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]([S:18][c:19]3[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]3[Cl:26])[s:27]2)[CH2:28][CH2:29]1 | ([#16;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]:[#16;a:4]).([C:5]-[NH2;D1;+0:6]) | 5bb56310c7e4f3afa8eb9f308cf2a936bbefe860ff713537ff3aa57d | 1 | 1 | null | 736 |
249,988 | 829,370 | 1,375,223 | [CH2:1]([S:3][C:4]1[C:9]([C:10]([O:12]C)=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:5]=1)[CH3:2].CO.C1COCC1.[Li+].[OH-].Cl>CCOC(C)=O>[CH2:1]([S:3][C:4]1[C:9]([C:10]([OH:12])=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=[C:6]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[N:5]=1)[CH3:2] | |f:1.2,3.4| | US08552200B2_1146 | 2,013 | C1CCOC1.CCOC(C)=O.CO.C[O:22][C:20]([c:19]1[c:4]([S:3][CH2:2][CH3:1])[n:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18])=[O:21].Cl.[Li+].[OH-]>>[CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[c:19]1[C:20](=[O:21])[OH:22] | 0.322008 | C1CCOC1~CO.CCOC(C)=O.CCSc1nc(N2CCOCC2)cc(C(F)(F)F)c1C(=O)OC.Cl.[Li+]~[OH-]>>CCSc1nc(N2CCOCC2)cc(C(F)(F)F)c1C(=O)O | C1CCOC1.CCOC(C)=O.CCSc1nc(N2CCOCC2)cc(C(F)(F)F)c1C(=O)OC.CO.Cl.[Li+].[OH-]>>CCSc1nc(N2CCOCC2)cc(C(F)(F)F)c1C(=O)O | US08552200B2_1146grants | b40fc9af2d8ca0042d4f6b43fc96c480fa87463bc009b123362debe6 | C1CCOC1.CCOC(C)=O.CO.C[O:22][C:20]([c:19]1[c:4]([S:3][CH2:2][CH3:1])[n:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18])=[O:21].Cl.[Li+].[OH-] | [CH3:1][CH2:2][S:3][c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[c:19]1[C:20](=[O:21])[OH:22] | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b499e0b68ab8cc89df665c73ba592c6e17427fbd5b75a0a04b8fb5db | 1 | 1 | C1CCOC1.CCOC(C)=O.CO.Cl.[Li+].[OH-] | 152 |
22,089 | 105,294 | 170,160 | C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Br.O>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][N:10]=2)=[CH:7][CH:8]=1 | null | US04723018_ | 1,988 | Br.CC(=O)O.C[O:17][c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:21][n:20]2)[cH:19][cH:18]1.O>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]2)[n:20][cH:21]1 | 0.917362 | Br.CC(=O)O.CCCCCCCCc1ccc(-c2ccc(OC)cc2)nc1.O>>CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1 | Br.CC(=O)O.CCCCCCCCc1ccc(-c2ccc(OC)cc2)nc1.O>>CCCCCCCCc1ccc(-c2ccc(O)cc2)nc1 | US04723018_grants | 9ec880d553e72d9a0e7a56c5c15c472af9348cce0cc9db8c4b1ce96f | Br.CC(=O)O.C[O:17][c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:21][n:20]2)[cH:19][cH:18]1.O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]2)[n:20][cH:21]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | Br.CC(=O)O.O | 48 |
325,837 | 1,058,313 | 1,797,293 | [C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[N:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.O.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]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=3)=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[N:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2] | |f:2.3.4,8.9.10.11.12| | US09422281B2_2284 | 2,016 | Br[c:11]1[c:7]([N+:8](=[O:9])[O-:10])[cH:6][c:5]2[c:23]([cH:22]1)[N:24]([C:25](=[O:26])[O:27][CH:28]([CH3:29])[CH3:30])[CH2:31][C@H:32]([CH3:33])[N:4]2[C:2]([CH3:1])=[O:3].C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21]2)OC1(C)C.O.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]>>[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21]3)[cH:22][c:23]2[N:24]([C:25](=[O:26])[O:27][CH:28]([CH3:29])[CH3:30])[CH2:31][C@@H:32]1[CH3:33] | 0.427474 | C1COCCO1.CC(=O)N1c2cc([N+](=O)[O-])c(Br)cc2N(C(=O)OC(C)C)C[C@@H]1C.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB(c2ccc(S(C)(=O)=O)cc2)OC1(C)C.O.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+]>>CC(=O)N1c2cc([N+](=O)[O-])c(-c3ccc(S(C)(=O)=O)cc3)cc2N(C(=O)OC(C)C)C[C@@H]1C | C1COCCO1.CC(=O)N1c2cc([N+](=O)[O-])c(Br)cc2N(C(=O)OC(C)C)C[C@@H]1C.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB(c2ccc(S(C)(=O)=O)cc2)OC1(C)C.O.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]>>CC(=O)N1c2cc([N+](=O)[O-])c(-c3ccc(S(C)(=O)=O)cc3)cc2N(C(=O)OC(C)C)C[C@@H]1C | US09422281B2_2284grants | 683ab0606ea73ca3baade20f1f97aa1bc82cb0274825aec22b94c609 | Br[c:11]1[c:7]([N+:8](=[O:9])[O-:10])[cH:6][c:5]2[c:23]([cH:22]1)[N:24]([C:25](=[O:26])[O:27][CH:28]([CH3:29])[CH3:30])[CH2:31][C@H:32]([CH3:33])[N:4]2[C:2]([CH3:1])=[O:3].C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21]2)OC1(C)C.O.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] | [CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11](-[c:12]3[cH:13][cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20][cH:21]3)[cH:22][c:23]2[N:24]([C:25](=[O:26])[O:27][CH:28]([CH3:29])[CH3:30])[CH2:31][C@@H:32]1[CH3:33] | ([c:5]:[c;H0;D3;+0:4](:[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C1(-C)-O-B(-[c;H0;D3;+0:4](:[c:5]):[c:6])-O-C-1(-C)-C) | 9070cdd4fb6f1677ab91185ae4f4e0309f05412abddf79c11415d35f | 0.5 | 2 | C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O.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] | 933 |
47,609 | 208,404 | 336,622 | [NH2:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:9]([CH2:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2.CO.O.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>>[NH2:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([O:18][CH3:27])=[O:17])=[C:9]([CH2:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2 | |f:2.3| | US05525602_ | 1,996 | Cc1ccc(S(=O)(=O)O)cc1.O.O[C:17]([CH2:16][CH2:15]/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([CH2:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[NH2:9])[C:21](=[O:22])[O:23][CH2:24]2)[CH3:14])=[O:18].[OH:19][CH3:20]>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([NH2:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH2:15][CH2:16][C:17](=[O:18])[O:19][CH3:20])[C:21](=[O:22])[O:23][CH2:24]2 | 0.80274 | CCc1c(C)c2c(c(N)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.CO.Cc1ccc(S(=O)(=O)O)cc1~O>>CCc1c(C)c2c(c(N)c1C/C=C(\C)CCC(=O)OC)C(=O)OC2 | CCc1c(C)c2c(c(N)c1C/C=C(\C)CCC(=O)O)C(=O)OC2.CO.Cc1ccc(S(=O)(=O)O)cc1.O>>CCc1c(C)c2c(c(N)c1C/C=C(\C)CCC(=O)OC)C(=O)OC2 | US05525602_grants | 3591e30b2fbef31e1802f06b86291e70fe153252dbf4dacaf4123044 | Cc1ccc(S(=O)(=O)O)cc1.O.O[C:17]([CH2:16][CH2:15]/[C:13](=[CH:12]/[CH2:11][c:10]1[c:3]([CH2:2][CH3:1])[c:4]([CH3:5])[c:6]2[c:7]([c:8]1[NH2:9])[C:21](=[O:22])[O:23][CH2:24]2)[CH3:14])=[O:18].[OH:19][CH3:20] | [CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[c:6]2[c:7]([c:8]([NH2:9])[c:10]1[CH2:11]/[CH:12]=[C:13](\[CH3:14])[CH2:15][CH2:16][C:17](=[O:18])[O:19][CH3:20])[C:21](=[O:22])[O:23][CH2:24]2 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C;D1;H3:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | Cc1ccc(S(=O)(=O)O)cc1.O | 17 |
414,943 | 1,707,169 | null | [CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:10]([NH2:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][C:28]([O:31][C:32](O[C:32]([O:31][C:28]([CH3:30])([CH3:29])[CH3:27])=[O:33])=[O:33])([CH3:30])[CH3:29]>C1COCC1>[C:28]([O:31][C:32](=[O:33])[NH:19][C@H:10]1[C@H:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)([CH3:30])([CH3:29])[CH3:27] | null | US20150166564A1_0490 | 2,015 | C1CCOC1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CCN(CC)CC.[NH2:8][C@@H:9]1[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C@H:20]1[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C@H:20]1[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | 0.215809 | C1CCOC1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.N[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1>>CC(C)(C)OC(=O)N[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1 | C1CCOC1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCN(CC)CC.N[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1>>CC(C)(C)OC(=O)N[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1 | US20150166564A1_0490apps | 9d0d3284cc8135f2392a5f5056050df5c17349c9bcc0e8a8fa582621 | C1CCOC1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].CCN(CC)CC.[NH2:8][C@@H:9]1[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C@H:20]1[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C@H:20]1[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1 | ([C:8]-[NH;D2;+0:9]-[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]-[NH2;D1;+0:9]) | e21cbc5dc2263b0652396beb92f05fda37bb9f2c606e45a3619c49bf | 1 | 1 | C1CCOC1.CCN(CC)CC | 631 |
416,416 | 1,725,590 | null | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[OH:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:25][C:26](C)([O-])C.[K+].C(I)C>CN(C)C=O>[CH2:25]([O:18][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=1)[CH3:26] | |f:1.2| | US20150210641A1_0222 | 2,015 | CC(C)(C)[O-].CN(C)C=O.I[CH2:2][CH3:1].[K+].[OH:3][CH:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]2)[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][CH:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]2)[cH:25][cH:26]1 | 0.870902 | CC(C)(C)[O-]~[K+].CCI.CN(C)C=O.COc1ccc(-c2ccc(C(O)c3ccncc3)cc2)cc1OC>>CCOC(c1ccncc1)c1ccc(-c2ccc(OC)c(OC)c2)cc1 | CC(C)(C)[O-].CCI.CN(C)C=O.COc1ccc(-c2ccc(C(O)c3ccncc3)cc2)cc1OC.[K+]>>CCOC(c1ccncc1)c1ccc(-c2ccc(OC)c(OC)c2)cc1 | US20150210641A1_0222apps | 5ae4e2f4322d32216c0a0b2523f10f6c0da49542e89d1bfd7bdc3308 | CC(C)(C)[O-].CN(C)C=O.I[CH2:2][CH3:1].[K+].[OH:3][CH:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]2)[cH:25][cH:26]1 | [CH3:1][CH2:2][O:3][CH:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24]2)[cH:25][cH:26]1 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[C;D1;H3:2])>>(I-[CH2;D2;+0:1]-[C;D1;H3:2]).([C:3]-[OH;D1;+0:4]) | 8c903ede93ede218ea763d890a28b2d4fa4d188f223a3117cf5050e7 | 1 | 1 | CC(C)(C)[O-].CN(C)C=O.[K+] | 307 |
381,404 | 951,936 | null | C([O:3][C:4](=[O:23])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:7]1=2)C.O[Li].O.Cl>CO>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:7]=2[CH:6]([CH2:5][C:4]([OH:23])=[O:3])[O:10]1 | |f:1.2| | US20100256092A1_0784 | 2,010 | CC[O:3][C:2](=[O:1])[CH2:4][CH:5]1[O:6][B:7]([OH:8])[c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]21.CO.Cl.O.[Li]O>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[O:6][B:7]([OH:8])[c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]21 | 0.798277 | CCOC(=O)CC1OB(O)c2cc(Oc3ccccc3)ccc21.CO.Cl.O~[Li]O>>O=C(O)CC1OB(O)c2cc(Oc3ccccc3)ccc21 | CCOC(=O)CC1OB(O)c2cc(Oc3ccccc3)ccc21.CO.Cl.O.[Li]O>>O=C(O)CC1OB(O)c2cc(Oc3ccccc3)ccc21 | US20100256092A1_0784apps | a395206ee2550562b14fb1183cfcdd65cd328f066c2f00d618a9d32b | CC[O:3][C:2](=[O:1])[CH2:4][CH:5]1[O:6][B:7]([OH:8])[c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]21.CO.Cl.O.[Li]O | [O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[O:6][B:7]([OH:8])[c:9]2[cH:10][c:11]([O:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]21 | ([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.[Li]O | 7 |
273,119 | 895,775 | 1,493,364 | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17](Cl)=[N:16][CH:15]=[CH:14][N:13]=1)(=[O:10])=[O:9].[C:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([OH:21])=[O:20]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17]([C:25]2[CH:26]=[CH:27][C:22]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=2)=[N:16][CH:15]=[CH:14][N:13]=1)(=[O:10])=[O:9] | null | US08796280B2_0221 | 2,014 | Cl[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[NH:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Cl:24].OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:26][cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[NH:14][S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[Cl:24])[cH:25][cH:26]1 | 0.734651 | O=C(O)c1ccc(B(O)O)cc1.O=S(=O)(Nc1nccnc1Cl)c1ccccc1Cl>>O=C(O)c1ccc(-c2nccnc2NS(=O)(=O)c2ccccc2Cl)cc1 | O=C(O)c1ccc(B(O)O)cc1.O=S(=O)(Nc1nccnc1Cl)c1ccccc1Cl>>O=C(O)c1ccc(-c2nccnc2NS(=O)(=O)c2ccccc2Cl)cc1 | US08796280B2_0221grants | 1da772b975e95ee913c5113b83909be7ab8695f3bf8122bb1a9ffd48 | Cl[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[NH:14][S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Cl:24].OB(O)[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:26][cH:25]1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[NH:14][S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[Cl:24])[cH:25][cH:26]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[#7;a:2])-[c;H0;D3;+0:5](:[c:6]):[c:7])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[#7;a:4]).(O-B(-O)-[c;H0;D3;+0:5](:[c:6]):[c:7]) | dcb2f4ca6a7134ddb59f59d454708c97a344949fdb3ba90016c3197b | 1 | 1 | null | 875 |
265,345 | 873,499 | 1,454,153 | [CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2.[O:16]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34]O)[CH2:30][CH2:29]3)=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1>[O:16]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34][O:14][C:13]([C:7]4[CH:8]=[N:9][C:10]5[C:5]([CH:6]=4)=[N:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=5)=[O:15])[CH2:30][CH2:29]3)=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1 | |f:2.3| | US08716280B2_0359 | 2,014 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl.O[C:10]([c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:34][c:33]2[cH:32]1)=[O:11].[OH:12][CH2:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([NH:18][CH2:19][c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH2:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH:18][CH2:19][c:20]4[cH:21][cH:22][c:23]5[c:24]([cH:25]4)[O:26][CH2:27][CH2:28][O:29]5)[CH2:30][CH2:31]3)[cH:32][c:33]2[n:34]1 | 0.92486 | CCN=C=NCCCN(C)C~Cl.CN(C)C=O.CN(C)c1ccncc1.COc1ccc2ncc(C(=O)O)cc2n1.OC[C@@H]1CC[C@@H](NCc2ccc3c(c2)OCCO3)CC1>>COc1ccc2ncc(C(=O)OC[C@@H]3CC[C@@H](NCc4ccc5c(c4)OCCO5)CC3)cc2n1 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.COc1ccc2ncc(C(=O)O)cc2n1.Cl.OC[C@@H]1CC[C@@H](NCc2ccc3c(c2)OCCO3)CC1>>COc1ccc2ncc(C(=O)OC[C@@H]3CC[C@@H](NCc4ccc5c(c4)OCCO5)CC3)cc2n1 | US08716280B2_0359grants | ea569915940761da13ae97225bde586eee735fe689b53cb25112dbeb | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl.O[C:10]([c:9]1[cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:34][c:33]2[cH:32]1)=[O:11].[OH:12][CH2:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([NH:18][CH2:19][c:20]2[cH:21][cH:22][c:23]3[c:24]([cH:25]2)[O:26][CH2:27][CH2:28][O:29]3)[CH2:30][CH2:31]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH2:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH:18][CH2:19][c:20]4[cH:21][cH:22][c:23]5[c:24]([cH:25]4)[O:26][CH2:27][CH2:28][O:29]5)[CH2:30][CH2:31]3)[cH:32][c:33]2[n:34]1 | ([#7;a:5]:[c:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[c:4]:[#7;a:5]).([C:6]-[OH;D1;+0:7]) | e4befd517abfaa6c24ee2bed88d2c492e451e1d0e951022f66b9b97f | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)C=O.CN(C)c1ccncc1.Cl | 521 |
39,490 | 176,857 | 283,980 | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.Cl>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[CH:8][CH:9]=1 | null | US05262509_ | 1,993 | CCO.Cl.O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=O)[O-])[cH:13][cH:14]2)[cH:15][cH:16]1.[Fe]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | 0.512444 | CCO.Cl.O.O=[N+]([O-])c1ccc(C=Cc2ccc([N+](=O)[O-])cc2)cc1.[Fe]>>Nc1ccc(C=Cc2ccc(N)cc2)cc1 | CCO.Cl.O.O=[N+]([O-])c1ccc(C=Cc2ccc([N+](=O)[O-])cc2)cc1.[Fe]>>Nc1ccc(C=Cc2ccc(N)cc2)cc1 | US05262509_grants | 0d220c7ce72b0d43ac30d2d541a382464a8ece8ed26429029a65852c | CCO.Cl.O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=O)[O-])[cH:13][cH:14]2)[cH:15][cH:16]1.[Fe] | [NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[CH:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | ([NH2;D1;+0:1]-[c:2].[NH2;D1;+0:3]-[c:4])>>(O=[N+;H0;D3:1](-[O-])-[c:2].O=[N+;H0;D3:3](-[O-])-[c:4]) | b52918586402c60354cd21a5a3d4340b19906d8e64b7776a6c1f9378 | 0 | 1 | CCO.Cl.O.[Fe] | 204 |
440,635 | 1,910,813 | null | [F:1][CH2:2][CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]([C:17](Cl)=[O:18])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][C:9]=2[O:20][CH3:21].[CH2:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23].Cl.C(Cl)Cl.O.C(Cl)Cl>ClCCl>[CH2:25]([N:24]([CH2:22][CH3:23])[C:17]([CH:12]1[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[O:20][CH3:21])[N:4]([CH2:3][CH2:2][F:1])[C:16]=2[CH2:15][CH2:14][CH2:13]1)=[O:18])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1 | |f:2.3,4.5| | US20160214936A1_0112 | 2,016 | Cl.ClCCl.ClCCl.ClCCl.Cl[C:11](=[O:12])[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[c:19]1[c:20]([O:21][CH3:22])[cH:23][cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][F:30].O.[CH3:1][CH2:2][NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][CH2:2][N:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[c:19]1[c:20]([O:21][CH3:22])[cH:23][cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][F:30] | 0.907969 | CCNCc1ccccc1.COc1cccc2c1c1c(n2CCF)CCCC1C(=O)Cl.ClCCl.ClCCl~O.Cl~ClCCl>>CCN(Cc1ccccc1)C(=O)C1CCCc2c1c1c(OC)cccc1n2CCF | CCNCc1ccccc1.COc1cccc2c1c1c(n2CCF)CCCC1C(=O)Cl.Cl.ClCCl.ClCCl.ClCCl.O>>CCN(Cc1ccccc1)C(=O)C1CCCc2c1c1c(OC)cccc1n2CCF | US20160214936A1_0112apps | abb1cb731f910b9561d22d2f4eb9457ca2f5546d5952dcdacf4a3cfd | Cl.ClCCl.ClCCl.ClCCl.Cl[C:11](=[O:12])[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[c:19]1[c:20]([O:21][CH3:22])[cH:23][cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][F:30].O.[CH3:1][CH2:2][NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | [CH3:1][CH2:2][N:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11](=[O:12])[CH:13]1[CH2:14][CH2:15][CH2:16][c:17]2[c:18]1[c:19]1[c:20]([O:21][CH3:22])[cH:23][cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][F:30] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[c:12]:1)>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[c:12]:1) | 29188a5b9c9c971c360ca7cbac1e55ff643207b99ae54454a152b303 | 1 | 1 | Cl.ClCCl.ClCCl.ClCCl.O | 240 |
367,186 | 716,266 | null | [NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[H-].[Na+].Br[CH2:18][CH2:19][O:20][CH3:21].O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([CH2:18][CH2:19][O:20][CH3:21])[C:6](=[O:12])[C:5]2([CH3:14])[CH3:13] | |f:1.2| | US20090143375A1_0254 | 2,009 | Br[CH2:4][CH2:3][O:2][CH3:1].CN(C)C=O.O.[H-].[NH:5]1[C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][c:13]([NH2:14])[c:15]([NH2:16])[cH:17][c:18]21.[Na+]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][c:13]([NH2:14])[c:15]([NH2:16])[cH:17][c:18]21 | 0.723809 | CC1(C)C(=O)Nc2cc(N)c(N)cc21.CN(C)C=O.COCCBr.O.[H-]~[Na+]>>COCCN1C(=O)C(C)(C)c2cc(N)c(N)cc21 | CC1(C)C(=O)Nc2cc(N)c(N)cc21.CN(C)C=O.COCCBr.O.[H-].[Na+]>>COCCN1C(=O)C(C)(C)c2cc(N)c(N)cc21 | US20090143375A1_0254apps | 3736a00f3c71624aafc1f681c02c5aa4edf0e6b0105959cdd3e62379 | Br[CH2:4][CH2:3][O:2][CH3:1].CN(C)C=O.O.[H-].[NH:5]1[C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][c:13]([NH2:14])[c:15]([NH2:16])[cH:17][c:18]21.[Na+] | [CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[c:11]2[cH:12][c:13]([NH2:14])[c:15]([NH2:16])[cH:17][c:18]21 | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[c:7])-[C:4](-[C:3])=[O;D1;H0:5])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]) | b53a00627033c015a02275a68480e22f4e46f9df18b7c92df7b6ba0d | 1 | 1 | CN(C)C=O.O.[H-].[Na+] | 367 |
372,938 | 814,763 | null | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.CCN(C(C)C)C(C)C.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]Br)[CH:24]=1>C1COCC1.CCOC(C)=O>[Br:22][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][CH:28]=1)[CH2:29][N:10]1[CH2:9][CH2:8][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1 | null | US20090325964A1_0168 | 2,009 | Br[CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([Br:1])[cH:20]1.C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[CH2:18][CH2:19]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][n:17]3)[CH2:18][CH2:19]2)[cH:20]1 | 0.85484 | BrCc1cccc(Br)c1.C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.c1ccc(N2CCNCC2)nc1>>Brc1cccc(CN2CCN(c3ccccn3)CC2)c1 | BrCc1cccc(Br)c1.C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.c1ccc(N2CCNCC2)nc1>>Brc1cccc(CN2CCN(c3ccccn3)CC2)c1 | US20090325964A1_0168apps | d39bcde4bf76d6d35286fb364ca049d50b5d1d680d64978290142d81 | Br[CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([Br:1])[cH:20]1.C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.[NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[CH2:18][CH2:19]1 | [Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][n:17]3)[CH2:18][CH2:19]2)[cH:20]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 83224be0473e190f3e9801b4a42490bc28eb62b70434bda042317a86 | 1 | 1 | C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O | 248 |
315,977 | 1,026,605 | 1,738,298 | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]3=[CH:7][C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[F:29]>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)=[CH:22][C:21]=1[F:29] | null | US09284321B2_1053 | 2,016 | Br[c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:16][c:15]2[c:14]1[n:19]1[c:18]([cH:17]2)[C:24](=[O:25])[NH:23][CH2:22][CH2:21][CH2:20]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([F:12])[cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[c:11]([F:12])[cH:13]2)[c:14]2[c:15]([cH:16]1)[cH:17][c:18]1[n:19]2[CH2:20][CH2:21][CH2:22][NH:23][C:24]1=[O:25] | 0.99223 | N#Cc1cc(Br)c2c(c1)cc1n2CCCNC1=O.OB(O)c1ccc(Cl)c(F)c1>>N#Cc1cc(-c2ccc(Cl)c(F)c2)c2c(c1)cc1n2CCCNC1=O | N#Cc1cc(Br)c2c(c1)cc1n2CCCNC1=O.OB(O)c1ccc(Cl)c(F)c1>>N#Cc1cc(-c2ccc(Cl)c(F)c2)c2c(c1)cc1n2CCCNC1=O | US09284321B2_1053grants | 749deda4cdfc2ba245ab12fe7d655b9b61008d76c99ef4f1fe4b3498 | Br[c:5]1[cH:4][c:3]([C:2]#[N:1])[cH:16][c:15]2[c:14]1[n:19]1[c:18]([cH:17]2)[C:24](=[O:25])[NH:23][CH2:22][CH2:21][CH2:20]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([F:12])[cH:13]1 | [N:1]#[C:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[c:11]([F:12])[cH:13]2)[c:14]2[c:15]([cH:16]1)[cH:17][c:18]1[n:19]2[CH2:20][CH2:21][CH2:22][NH:23][C:24]1=[O:25] | ([#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 | null | 833 |
359,839 | 619,193 | null | Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>CCO>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1 | |f:2.3| | US20080255155A1_0750 | 2,008 | CCO.Cl[c:4]1[cH:3][c:2]([Cl:1])[n:14][cH:13][n:12]1.O=C([O-])O.[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[Na+]>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][cH:13][n:14]1 | 0.570935 | CCO.Clc1cc(Cl)ncn1.Nc1ccccc1.O=C([O-])O~[Na+]>>Clc1cc(Nc2ccccc2)ncn1 | CCO.Clc1cc(Cl)ncn1.Nc1ccccc1.O=C([O-])O.[Na+]>>Clc1cc(Nc2ccccc2)ncn1 | US20080255155A1_0750apps | e4c1ee9383d5cbd4707e35f09e84659a2fd84944e35c5107c908ae54 | CCO.Cl[c:4]1[cH:3][c:2]([Cl:1])[n:14][cH:13][n:12]1.O=C([O-])O.[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[Na+] | [Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][cH:13][n:14]1 | ([c:8]-[NH;D2;+0:7]-[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).([NH2;D1;+0:7]-[c:8]) | db1d2c86680d6406cfc43d406a7d37a82476d5b9bb83e186c7450e56 | 1 | 1 | CCO.O=C([O-])O.[Na+] | 161 |