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
|
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
61,373 | 259,176 | 438,694 | [NH2:1][C@H:2]([C:7]([C@@H:9]1[C@@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]([CH2:17][OH:18])[O:11][C@@:10]1([NH2:53])[N:19]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:20](=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[C:54]([O:58][C:59]([NH:61][CH2:62][C:63]([NH:65][CH2:66][C:67](O)=[O:68])=[O:64])=[O:60])([CH3:57])([CH3:56])[CH3:55]>O1CCCC1>[C:54]([O:58][C:59]([NH:61][CH2:62][C:63]([NH:65][CH2:66][C:67]([NH:1][C@H:2]([C:7]([C@@H:9]1[C@@H:14]([OH:15])[C@H:13]([OH:16])[C@@H:12]([CH2:17][OH:18])[O:11][C@@:10]1([NH2:53])[N:19]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:20](=[O:38])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:68])=[O:64])=[O:60])([CH3:57])([CH3:56])[CH3:55] | null | US05905071_ | 1,999 | C1CCOC1.O[C:54](=[O:55])[CH2:56][NH:57][C:58](=[O:59])[CH2:60][NH:61][C:62](=[O:63])[O:64][C:65]([CH3:66])([CH3:67])[CH3:68].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@:35]1([NH2:36])[O:37][C@H:38]([CH2:39][OH:40])[C@@H:41]([OH:42])[C@H:43]([OH:44])[C@H:45]1[C:46](=[O:47])[C@H:48]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH2:53]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@:35]1([NH2:36])[O:37][C@H:38]([CH2:39][OH:40])[C@@H:41]([OH:42])[C@H:43]([OH:44])[C@H:45]1[C:46](=[O:47])[C@H:48]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH:53][C:54](=[O:55])[CH2:56][NH:57][C:58](=[O:59])[CH2:60][NH:61][C:62](=[O:63])[O:64][C:65]([CH3:66])([CH3:67])[CH3:68] | 0.206004 | C1CCOC1.CC(C)(C)OC(=O)NCC(=O)NCC(=O)O.CCCCCCCC/C=C\CCCCCCCC(=O)N(CCCCCCCCCCCCCC)[C@]1(N)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1C(=O)[C@@H](N)CC(C)C>>CCCCCCCC/C=C\CCCCCCCC(=O)N(CCCCCCCCCCCCCC)[C@]1(N)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1C(=O)[C@H](CC(C)C)NC(=O)CNC(=O)CNC(=O)OC(C)(C)C | C1CCOC1.CC(C)(C)OC(=O)NCC(=O)NCC(=O)O.CCCCCCCC/C=C\CCCCCCCC(=O)N(CCCCCCCCCCCCCC)[C@]1(N)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1C(=O)[C@@H](N)CC(C)C>>CCCCCCCC/C=C\CCCCCCCC(=O)N(CCCCCCCCCCCCCC)[C@]1(N)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1C(=O)[C@H](CC(C)C)NC(=O)CNC(=O)CNC(=O)OC(C)(C)C | US05905071_grants | ff51ade0acfd3852fd549ca59b2ecded490fb16c5b3b2e6c38cc0a8a | C1CCOC1.O[C:54](=[O:55])[CH2:56][NH:57][C:58](=[O:59])[CH2:60][NH:61][C:62](=[O:63])[O:64][C:65]([CH3:66])([CH3:67])[CH3:68].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@:35]1([NH2:36])[O:37][C@H:38]([CH2:39][OH:40])[C@@H:41]([OH:42])[C@H:43]([OH:44])[C@H:45]1[C:46](=[O:47])[C@H:48]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH2:53] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@:35]1([NH2:36])[O:37][C@H:38]([CH2:39][OH:40])[C@@H:41]([OH:42])[C@H:43]([OH:44])[C@H:45]1[C:46](=[O:47])[C@H:48]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH:53][C:54](=[O:55])[CH2:56][NH:57][C:58](=[O:59])[CH2:60][NH:61][C:62](=[O:63])[O:64][C:65]([CH3:66])([CH3:67])[CH3:68] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[C:6]=[O;D1;H0:7])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5]-[C:6]=[O;D1;H0:7]) | 32d50fe4831ebbd433ee349cc5a3db8146a7ececfeb444c611894dca | 0.5 | 2 | C1CCOC1 | 645 |
135,235 | 490,854 | 826,959 | C([O:8][C:9]1[CH:41]=[CH:40][C:12]2[C:13]3[N:14]([CH2:25][C:26]4[CH:39]=[CH:38][C:29]([O:30][CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:28][CH:27]=4)[C:15]4[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=4[C:21]=3[O:22][C:11]=2[CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[CH2:36]([N:33]([CH2:34][CH3:35])[CH2:32][CH2:31][O:30][C:29]1[CH:38]=[CH:39][C:26]([CH2:25][N:14]2[C:15]3[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=3[C:21]3[O:22][C:11]4[CH:10]=[C:9]([OH:8])[CH:41]=[CH:40][C:12]=4[C:13]2=3)=[CH:27][CH:28]=1)[CH3:37] | null | US07338973B2_0694 | 2,008 | CCO.[Pd].c1ccc(C[O:28][c:27]2[cH:26][c:25]3[o:24][c:23]4[c:22]5[c:15]([n:14]([CH2:13][c:12]6[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:34][cH:33]6)[c:32]4[c:31]3[cH:30][cH:29]2)[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21]5)cc1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][n:14]2[c:15]3[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][c:22]3[c:23]3[o:24][c:25]4[cH:26][c:27]([OH:28])[cH:29][cH:30][c:31]4[c:32]23)[cH:33][cH:34]1 | 0.838328 | CCN(CC)CCOc1ccc(Cn2c3ccc(OC)cc3c3oc4cc(OCc5ccccc5)ccc4c32)cc1.CCO.[Pd]>>CCN(CC)CCOc1ccc(Cn2c3ccc(OC)cc3c3oc4cc(O)ccc4c32)cc1 | CCN(CC)CCOc1ccc(Cn2c3ccc(OC)cc3c3oc4cc(OCc5ccccc5)ccc4c32)cc1.CCO.[Pd]>>CCN(CC)CCOc1ccc(Cn2c3ccc(OC)cc3c3oc4cc(O)ccc4c32)cc1 | US07338973B2_0694grants | c4418d4827a7c8d62ab45f1ee0de79edd2da5b30b2750c4772ef18ce | CCO.[Pd].c1ccc(C[O:28][c:27]2[cH:26][c:25]3[o:24][c:23]4[c:22]5[c:15]([n:14]([CH2:13][c:12]6[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:34][cH:33]6)[c:32]4[c:31]3[cH:30][cH:29]2)[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21]5)cc1 | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][n:14]2[c:15]3[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][c:22]3[c:23]3[o:24][c:25]4[cH:26][c:27]([OH:28])[cH:29][cH:30][c:31]4[c:32]23)[cH:33][cH:34]1 | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | CCO.[Pd] | 23 |
434,023 | 1,865,944 | null | [C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:21]([NH:23][C@@H:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@H:27]([O:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:41]([N:44]5[C@H:49]([CH3:50])[CH2:48][CH2:47][CH2:46][C@@H:45]5[CH3:51])=[N:42][N:43]=4)[CH:40]=3)[CH2:26][CH2:25]2)=[O:22])[N:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([O:16][CH2:17][CH2:18][OH:19])[CH:15]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:52][S:53](Cl)(=[O:55])=[O:54].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:21]([NH:23][C@@H:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@H:27]([O:34][C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:41]([N:44]5[C@H:49]([CH3:50])[CH2:48][CH2:47][CH2:46][C@@H:45]5[CH3:51])=[N:42][N:43]=4)[CH:40]=3)[CH2:26][CH2:25]2)=[O:22])[N:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][O:19][S:53]([CH3:52])(=[O:55])=[O:54])[CH:13]=[N:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3] | null | US20160108040A1_0249 | 2,016 | CCN(C(C)C)C(C)C.ClCCl.Cl[S:43]([CH3:44])(=[O:45])=[O:46].[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][C@@H:17]3[CH2:18][CH2:19][C@H:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][cH:37][c:38]([O:39][CH2:40][CH2:41][OH:42])[cH:47]4)[c:48]4[cH:49][cH:50][cH:51][cH:52][c:53]43)[cH:54][n:55]12>>[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][C@@H:17]3[CH2:18][CH2:19][C@H:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][cH:37][c:38]([O:39][CH2:40][CH2:41][O:42][S:43]([CH3:44])(=[O:45])=[O:46])[cH:47]4)[c:48]4[cH:49][cH:50][cH:51][cH:52][c:53]43)[cH:54][n:55]12 | 0.263768 | CCN(C(C)C)C(C)C.CS(=O)(=O)Cl.C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cncc(OCCO)c4)c4ccccc43)cn12.ClCCl>>C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cncc(OCCOS(C)(=O)=O)c4)c4ccccc43)cn12 | CCN(C(C)C)C(C)C.CS(=O)(=O)Cl.C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cncc(OCCO)c4)c4ccccc43)cn12.ClCCl>>C[C@@H]1CCC[C@H](C)N1c1nnc2ccc(O[C@@H]3CC[C@H](NC(=O)Nc4cc(C(C)(C)C)nn4-c4cncc(OCCOS(C)(=O)=O)c4)c4ccccc43)cn12 | US20160108040A1_0249apps | cdc5d39dd3e5b3b88c4a6aecaa7ff810231fba3f5568d052d919b03a | CCN(C(C)C)C(C)C.ClCCl.Cl[S:43]([CH3:44])(=[O:45])=[O:46].[CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][C@@H:17]3[CH2:18][CH2:19][C@H:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][cH:37][c:38]([O:39][CH2:40][CH2:41][OH:42])[cH:47]4)[c:48]4[cH:49][cH:50][cH:51][cH:52][c:53]43)[cH:54][n:55]12 | [CH3:1][C@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH3:7])[N:8]1[c:9]1[n:10][n:11][c:12]2[cH:13][cH:14][c:15]([O:16][C@@H:17]3[CH2:18][CH2:19][C@H:20]([NH:21][C:22](=[O:23])[NH:24][c:25]4[cH:26][c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[n:32][n:33]4-[c:34]4[cH:35][n:36][cH:37][c:38]([O:39][CH2:40][CH2:41][O:42][S:43]([CH3:44])(=[O:45])=[O:46])[cH:47]4)[c:48]4[cH:49][cH:50][cH:51][cH:52][c:53]43)[cH:54][n:55]12 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 0 |
188,234 | 649,481 | 1,073,863 | [O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C@H:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:9]([OH:11])=O)[CH2:3]1.C(Cl)(=O)C(Cl)=O.[C:28]([Si:32]([CH3:43])([CH3:42])[O:33][CH2:34][CH2:35][N:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1)([CH3:31])([CH3:30])[CH3:29].N1C(C)=CC=CC=1C>C(Cl)Cl>[C:28]([Si:32]([CH3:43])([CH3:42])[O:33][CH2:34][CH2:35][N:36]1[CH:40]=[CH:39][C:38]([NH:41][C:9](=[O:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH2:7][C@H:4]2[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]2)=[N:37]1)([CH3:31])([CH3:30])[CH3:29] | null | US07935699B2_0590 | 2,011 | Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl.O[C:16](=[O:17])[C@H:18]([CH2:19][C@H:20]1[CH2:21][CH2:22][C:23](=[O:24])[CH2:25]1)[c:26]1[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]([NH2:15])[n:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[C@H:18]([CH2:19][C@H:20]2[CH2:21][CH2:22][C:23](=[O:24])[CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]2)[n:36]1 | 0.069397 | CC(C)(C)[Si](C)(C)OCCn1ccc(N)n1.Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl.O=C1CC[C@H](C[C@@H](C(=O)O)c2cccc(C(F)(F)F)c2)C1>>CC(C)(C)[Si](C)(C)OCCn1ccc(NC(=O)[C@H](C[C@H]2CCC(=O)C2)c2cccc(C(F)(F)F)c2)n1 | CC(C)(C)[Si](C)(C)OCCn1ccc(N)n1.Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl.O=C1CC[C@H](C[C@@H](C(=O)O)c2cccc(C(F)(F)F)c2)C1>>CC(C)(C)[Si](C)(C)OCCn1ccc(NC(=O)[C@H](C[C@H]2CCC(=O)C2)c2cccc(C(F)(F)F)c2)n1 | US07935699B2_0590grants | b5b503f591493844ca3756822e641c5d4e1536c8d5303373f9557ca1 | Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl.O[C:16](=[O:17])[C@H:18]([CH2:19][C@H:20]1[CH2:21][CH2:22][C:23](=[O:24])[CH2:25]1)[c:26]1[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]1.[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]([NH2:15])[n:36]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][n:11]1[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[C@H:18]([CH2:19][C@H:20]2[CH2:21][CH2:22][C:23](=[O:24])[CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]2)[n:36]1 | ([#7;a:4]:[#7;a:5]:[c:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7;a:4]:[#7;a:5]:[c:6]-[NH2;D1;+0:7]) | ac6bdb904c3bb8bbc59a5a6dd19b3afc2fd26ad6ace0ef77a514568f | 1 | 1 | Cc1cccc(C)n1.ClCCl.O=C(Cl)C(=O)Cl | 795 |
406,062 | 1,538,764 | null | [Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:13])[CH:3]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>CO.CCOC(C)=O>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([Cl:13])[CH:3]=1 | |f:2.3| | US20140171315A1_1044 | 2,014 | CCOC(C)=O.C[Si](C)(C)C=[N+]=[N-].O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]([Br:11])[cH:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]([Br:11])[cH:12][c:13]1[Cl:14] | 0.742649 | CCOC(C)=O~CO.COc1cc(C(=O)O)c(Cl)cc1Br.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)c1cc(OC)c(Br)cc1Cl | CCOC(C)=O.CO.COc1cc(C(=O)O)c(Cl)cc1Br.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)c1cc(OC)c(Br)cc1Cl | US20140171315A1_1044apps | 09d253038f042bd2cfeffe62ec5a451d1098a2ed1772ffa6f199e748 | CCOC(C)=O.C[Si](C)(C)C=[N+]=[N-].O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]([Br:11])[cH:12][c:13]1[Cl:14] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]([Br:11])[cH:12][c:13]1[Cl:14] | ([CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3]=[O;D1;H0:2])>>(O-[CH3;D1;+0:1]).([O;D1;H0:2]=[C:3]-[OH;D1;+0:4]) | e189425e090fce77131c907ebf1468461240dd27d4457a40d701e43e | 1 | 1 | CCOC(C)=O.C[Si](C)(C)C=[N+]=[N-] | 195 |
174,448 | 609,726 | 1,011,066 | [CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH2:34][C:35]([O:37]C)=[O:36])=[CH:13][CH:12]=1.Cl>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:15][CH:16]=1 | |f:3.4| | US07790715B2_0301 | 2,010 | C1COCCO1.C[O:39][C:37]([CH2:36][CH2:35][c:34]1[c:29]([O:28][CH2:27][CH2:26][O:25][CH:24]2[CH:19]([c:18]3[cH:17][cH:16][c:15]([O:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][c:8]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]4)[cH:41][cH:40]3)[CH2:20][CH2:21][NH:22][CH2:23]2)[cH:30][cH:31][cH:32][cH:33]1)=[O:38].Cl.[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][O:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH:24]2[O:25][CH2:26][CH2:27][O:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[CH2:35][CH2:36][C:37](=[O:38])[OH:39])[cH:40][cH:41]1 | 0.870341 | C1COCCO1.COC(=O)CCc1ccccc1OCCOC1CNCCC1c1ccc(OCCCOCc2ccccc2OC)cc1.Cl.[Na+]~[OH-]>>COc1ccccc1COCCCOc1ccc(C2CCNCC2OCCOc2ccccc2CCC(=O)O)cc1 | C1COCCO1.COC(=O)CCc1ccccc1OCCOC1CNCCC1c1ccc(OCCCOCc2ccccc2OC)cc1.Cl.[Na+].[OH-]>>COc1ccccc1COCCCOc1ccc(C2CCNCC2OCCOc2ccccc2CCC(=O)O)cc1 | US07790715B2_0301grants | 8d54f51d47349b7ee687f7fe960674025f649ecc35c3fc1bef8a4f54 | C1COCCO1.C[O:39][C:37]([CH2:36][CH2:35][c:34]1[c:29]([O:28][CH2:27][CH2:26][O:25][CH:24]2[CH:19]([c:18]3[cH:17][cH:16][c:15]([O:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][c:8]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]4)[cH:41][cH:40]3)[CH2:20][CH2:21][NH:22][CH2:23]2)[cH:30][cH:31][cH:32][cH:33]1)=[O:38].Cl.[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][O:10][CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH:24]2[O:25][CH2:26][CH2:27][O:28][c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[CH2:35][CH2:36][C:37](=[O:38])[OH:39])[cH:40][cH:41]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | C1COCCO1.Cl.[Na+].[OH-] | 88 |
223,361 | 749,458 | 1,233,800 | [CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][C:3]=1[C:10]1[N:14]([CH3:15])[N:13]=[CH:12][C:11]=1[CH2:16][CH2:17][CH3:18].[NH2:19][C@@H:20]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([F:43])([F:42])[F:41])[CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl>[O:31]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:32])[N:22]1[CH2:21][C@@H:20]([NH:19][C:7]([C:5]1[S:6][C:2]([CH3:1])=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[CH:12][C:11]=2[CH2:16][CH2:17][CH3:18])[CH:4]=1)=[O:9])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([F:42])([F:41])[F:43] | |f:3.4| | US08273782B2_1263 | 2,012 | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[P-](F)(F)(F)(F)F.O[C:13]([c:12]1[cH:11][c:10](-[c:9]2[c:4]([CH2:3][CH2:2][CH3:1])[cH:5][n:6][n:7]2[CH3:8])[c:41]([CH3:42])[s:40]1)=[O:14].[NH2:15][C@@H:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24]([F:25])([F:26])[F:27])[CH2:28][N:29]1[C:30](=[O:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]2[C:38]1=[O:39]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][n:6][n:7]([CH3:8])[c:9]1-[c:10]1[cH:11][c:12]([C:13](=[O:14])[NH:15][C@@H:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]([F:25])([F:26])[F:27])[CH2:28][N:29]2[C:30](=[O:31])[c:32]3[cH:33][cH:34][cH:35][cH:36][c:37]3[C:38]2=[O:39])[s:40][c:41]1[CH3:42] | 0.251561 | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1~F[P-](F)(F)(F)(F)F.CCCc1cnn(C)c1-c1cc(C(=O)O)sc1C.CCN(C(C)C)C(C)C.ClCCl.N[C@@H](Cc1ccccc1C(F)(F)F)CN1C(=O)c2ccccc2C1=O>>CCCc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2ccccc2C(F)(F)F)CN2C(=O)c3ccccc3C2=O)sc1C | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCCc1cnn(C)c1-c1cc(C(=O)O)sc1C.CCN(C(C)C)C(C)C.ClCCl.F[P-](F)(F)(F)(F)F.N[C@@H](Cc1ccccc1C(F)(F)F)CN1C(=O)c2ccccc2C1=O>>CCCc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2ccccc2C(F)(F)F)CN2C(=O)c3ccccc3C2=O)sc1C | US08273782B2_1263grants | 6adbfedee014ef0d122181be96d5b92cad7052729e20f7591f924ae2 | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[P-](F)(F)(F)(F)F.O[C:13]([c:12]1[cH:11][c:10](-[c:9]2[c:4]([CH2:3][CH2:2][CH3:1])[cH:5][n:6][n:7]2[CH3:8])[c:41]([CH3:42])[s:40]1)=[O:14].[NH2:15][C@@H:16]([CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24]([F:25])([F:26])[F:27])[CH2:28][N:29]1[C:30](=[O:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][c:37]2[C:38]1=[O:39] | [CH3:1][CH2:2][CH2:3][c:4]1[cH:5][n:6][n:7]([CH3:8])[c:9]1-[c:10]1[cH:11][c:12]([C:13](=[O:14])[NH:15][C@@H:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]([F:25])([F:26])[F:27])[CH2:28][N:29]2[C:30](=[O:31])[c:32]3[cH:33][cH:34][cH:35][cH:36][c:37]3[C:38]2=[O:39])[s:40][c:41]1[CH3:42] | ([#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 | Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[P-](F)(F)(F)(F)F | 736 |
80,256 | 324,625 | 550,159 | S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:25]([OH:27])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.[CH2:28]=[C:29]([CH3:31])[CH3:30]>O.C1(C)C=CC=CC=1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:25]([O:27][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1 | |f:0.1| | US06369266B1_ | 2,002 | Cc1ccccc1.O.O=S(=O)(O)O.O=S(=O)([O-])[O-].[C:15](=[CH2:16])([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12](=[O:13])[OH:14])[cH:19][cH:20]1.[Mg+2]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1 | 0.515618 | C=C(C)C.Cc1ccc(-c2ccccc2C(=O)O)cc1.Cc1ccccc1.O.O=S(=O)(O)O.O=S(=O)([O-])[O-]~[Mg+2]>>Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1 | C=C(C)C.Cc1ccc(-c2ccccc2C(=O)O)cc1.Cc1ccccc1.O.O=S(=O)(O)O.O=S(=O)([O-])[O-].[Mg+2]>>Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1 | US06369266B1_grants | 082a390a51fd34aa269d70bfac77add0b7e90d35f0a2a0431f829f29 | Cc1ccccc1.O.O=S(=O)(O)O.O=S(=O)([O-])[O-].[C:15](=[CH2:16])([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12](=[O:13])[OH:14])[cH:19][cH:20]1.[Mg+2] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1 | ([C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[O;H0;D2;+0:7]-[C:6]=[O;D1;H0:5])>>([C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH2;D1;+0:4]).([O;D1;H0:5]=[C:6]-[OH;D1;+0:7]) | 18ecf55fc019f98b847fd4b786d74332020de9e86518836cf73db86b | 1 | 1 | Cc1ccccc1.O.O=S(=O)(O)O.O=S(=O)([O-])[O-].[Mg+2] | 511 |
100,997 | 388,129 | 663,530 | [CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])=[O:25])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH2:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[F:35][C:36]([F:47])([F:46])[C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40](Cl)=[O:41]>>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=2[Cl:32])=[O:25])=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][NH:15][C:40]([C:39]2[CH:43]=[CH:44][CH:45]=[C:37]([C:36]([F:35])([F:46])[F:47])[CH:38]=2)=[O:41])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:7] | null | US06806365B2_ | 2,004 | Cl[C:31](=[O:32])[c:33]1[cH:34][cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]2[Cl:21])[cH:22][cH:23]1)[NH:24][C:25](=[O:26])[C:27]1([CH2:28][CH2:29][NH2:30])[CH2:43][CH2:44][CH2:45][CH2:46]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]2[Cl:21])[cH:22][cH:23]1)[NH:24][C:25](=[O:26])[C:27]1([CH2:28][CH2:29][NH:30][C:31](=[O:32])[c:33]2[cH:34][cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]2)[CH2:43][CH2:44][CH2:45][CH2:46]1 | 0.227388 | COC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cccc2Cl)cc1)NC(=O)C1(CCN)CCCC1.O=C(Cl)c1cccc(C(F)(F)F)c1>>COC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cccc2Cl)cc1)NC(=O)C1(CCNC(=O)c2cccc(C(F)(F)F)c2)CCCC1 | COC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cccc2Cl)cc1)NC(=O)C1(CCN)CCCC1.O=C(Cl)c1cccc(C(F)(F)F)c1>>COC(=O)[C@H](Cc1ccc(NC(=O)c2c(Cl)cccc2Cl)cc1)NC(=O)C1(CCNC(=O)c2cccc(C(F)(F)F)c2)CCCC1 | US06806365B2_grants | c261092d9a3c7a8ba1bb05501f6ee0f36a305ad184b0697740462689 | Cl[C:31](=[O:32])[c:33]1[cH:34][cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]2[Cl:21])[cH:22][cH:23]1)[NH:24][C:25](=[O:26])[C:27]1([CH2:28][CH2:29][NH2:30])[CH2:43][CH2:44][CH2:45][CH2:46]1 | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[c:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]2[Cl:21])[cH:22][cH:23]1)[NH:24][C:25](=[O:26])[C:27]1([CH2:28][CH2:29][NH:30][C:31](=[O:32])[c:33]2[cH:34][cH:35][cH:36][c:37]([C:38]([F:39])([F:40])[F:41])[cH:42]2)[CH2:43][CH2:44][CH2:45][CH2:46]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 04f622b60f06614bfdc3f8c27947d26b216da996402159ccfe3a0fc7 | 1 | 1 | null | 271 |
46,978 | 205,906 | 332,783 | [CH2:1]([O:8][C:9]([N:11]1[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:31])[CH2:21][S:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:46])C=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:31])[CH2:21][S:22]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[O:46])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | null | US05506256_ | 1,996 | ClCCl.O=C(O[OH:8])c1cccc(Cl)c1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7][CH2:9][CH:10]([OH:11])[C@@H:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][CH2:22][N:23]2[C:24](=[O:25])[O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])[CH2:9][CH:10]([OH:11])[C@@H:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][CH2:22][N:23]2[C:24](=[O:25])[O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1 | 0.551671 | COc1ccc(SCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OCc2ccccc2)cc1.ClCCl.O=C(OO)c1cccc(Cl)c1>>COc1ccc(S(=O)CC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OCc2ccccc2)cc1 | COc1ccc(SCC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OCc2ccccc2)cc1.ClCCl.O=C(OO)c1cccc(Cl)c1>>COc1ccc(S(=O)CC(O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)OCc2ccccc2)cc1 | US05506256_grants | eeabc7de76d97e224f7552dbad15927ed8b376a9048a07d400b84cb3 | ClCCl.O=C(O[OH:8])c1cccc(Cl)c1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7][CH2:9][CH:10]([OH:11])[C@@H:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][CH2:22][N:23]2[C:24](=[O:25])[O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])[CH2:9][CH:10]([OH:11])[C@@H:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][CH2:22][N:23]2[C:24](=[O:25])[O:26][CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1 | ([C:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4])>>(Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1).([C:2]-[S;H0;D2;+0:3]-[c:4]) | 3eca0f9955a304f24f0e70d3d79ae37309609db264458c56921bc8cd | 1 | 1 | ClCCl | 500 |
106,640 | 405,573 | 692,654 | [F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10][CH:9]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:26]=1[O:33][CH3:34])=[O:7]>CO.[C].[Pd]>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:37]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:26]=1[O:33][CH3:34])=[O:7] | |f:2.3| | US06924278B2_0543 | 2,005 | CO.O=C(OCc1ccccc1)[N:11]1[CH2:10][CH:9]([CH2:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]2[O:32][CH3:33])[N:14]([C:15](=[O:16])[c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[CH2:13][CH2:12]1.[C].[Pd]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH:9]2[CH2:10][NH:11][CH2:12][CH2:13][N:14]2[C:15](=[O:16])[c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[c:31]1[O:32][CH3:33] | 0.094784 | CO.COc1cccc(CC2CN(C(=O)OCc3ccccc3)CCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1OC.[C]~[Pd]>>COc1cccc(CC2CNCCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1OC | CO.COc1cccc(CC2CN(C(=O)OCc3ccccc3)CCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1OC.[C].[Pd]>>COc1cccc(CC2CNCCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c1OC | US06924278B2_0543grants | 486c09d38f6a515da600f12743932e66186e3672699798f6757727d6 | CO.O=C(OCc1ccccc1)[N:11]1[CH2:10][CH:9]([CH2:8][c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]2[O:32][CH3:33])[N:14]([C:15](=[O:16])[c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[CH2:13][CH2:12]1.[C].[Pd] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][CH:9]2[CH2:10][NH:11][CH2:12][CH2:13][N:14]2[C:15](=[O:16])[c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[c:31]1[O:32][CH3:33] | ([C:2]-[NH;D2;+0:1]-[C:3])>>(O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 5a4b471314a9d16582c772175d4da637e8cc4c358126acefcc826e38 | 1 | 1 | CO.[C].[Pd] | 428 |
362,219 | 647,550 | null | [NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7](Br)[C:6]=2[N:5]=[C:4]2[CH2:13][N:14]([CH2:17][CH2:18][CH3:19])[C:15](=[O:16])[C:3]=12.[Cl:20][C:21]1[C:26](B(O)O)=[CH:25][CH:24]=[C:23]([CH3:30])[N:22]=1>>[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:26]3[C:21]([Cl:20])=[N:22][C:23]([CH3:30])=[CH:24][CH:25]=3)[C:6]=2[N:5]=[C:4]2[CH2:13][N:14]([CH2:17][CH2:18][CH3:19])[C:15](=[O:16])[C:3]=12 | null | US20080318943A1_0941 | 2,008 | Br[c:9]1[c:8]2[n:7][c:6]3[c:24]([c:22]([NH2:23])[c:21]2[cH:20][cH:19][cH:18]1)[C:25](=[O:26])[N:4]([CH2:3][CH2:2][CH3:1])[CH2:5]3.OB(O)[c:10]1[cH:11][cH:12][c:13]([CH3:14])[n:15][c:16]1[Cl:17]>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][c:6]2[n:7][c:8]3[c:9](-[c:10]4[cH:11][cH:12][c:13]([CH3:14])[n:15][c:16]4[Cl:17])[cH:18][cH:19][cH:20][c:21]3[c:22]([NH2:23])[c:24]2[C:25]1=[O:26] | 0.991845 | CCCN1Cc2nc3c(Br)cccc3c(N)c2C1=O.Cc1ccc(B(O)O)c(Cl)n1>>CCCN1Cc2nc3c(-c4ccc(C)nc4Cl)cccc3c(N)c2C1=O | CCCN1Cc2nc3c(Br)cccc3c(N)c2C1=O.Cc1ccc(B(O)O)c(Cl)n1>>CCCN1Cc2nc3c(-c4ccc(C)nc4Cl)cccc3c(N)c2C1=O | US20080318943A1_0941apps | fd6e3b2f07fcb745faf28f4c2244e3c038245ac64985f2d076551586 | Br[c:9]1[c:8]2[n:7][c:6]3[c:24]([c:22]([NH2:23])[c:21]2[cH:20][cH:19][cH:18]1)[C:25](=[O:26])[N:4]([CH2:3][CH2:2][CH3:1])[CH2:5]3.OB(O)[c:10]1[cH:11][cH:12][c:13]([CH3:14])[n:15][c:16]1[Cl:17] | [CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][c:6]2[n:7][c:8]3[c:9](-[c:10]4[cH:11][cH:12][c:13]([CH3:14])[n:15][c:16]4[Cl:17])[cH:18][cH:19][cH:20][c:21]3[c:22]([NH2:23])[c:24]2[C:25]1=[O:26] | ([#7;a:8]:[c:7]:[c;H0;D3;+0:5](:[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4])>>(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]:[#7;a:8]) | 70150d81f52513da33dee3f20d0f6a7e22a26764b7344cc59fad14a1 | 0.5 | 2 | null | 883 |
120,472 | 447,012 | 759,358 | CS(O[CH2:6][CH2:7][CH2:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)(=O)=O.[CH2:29]1[CH:33]2[CH2:34][NH:35][CH2:36][CH:32]2[CH2:31][N:30]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:8][CH2:7][CH2:6][N:35]2[CH2:34][CH:33]3[CH2:29][N:30]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH:32]3[CH2:36]2)=[CH:26][CH:25]=1)#[N:28] | |f:2.3.4| | US07144914B2_0452 | 2,006 | CC#N.CS(=O)(=O)O[CH2:11][CH2:10][CH2:9][CH:8]([O:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35]1)[c:27]1[cH:28][cH:29][c:30]([C:31]#[N:32])[cH:33][cH:34]1.O=C([O-])[O-].[Cs+].[Cs+].[NH:12]1[CH2:13][CH:14]2[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH:25]2[CH2:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH:14]3[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH:25]3[CH2:26]2)[c:27]2[cH:28][cH:29][c:30]([C:31]#[N:32])[cH:33][cH:34]2)[cH:35][c:36]1[O:37][CH3:38] | 0.335248 | CC#N.CC(C)(C)OC(=O)N1CC2CNCC2C1.COc1ccc(OC(CCCOS(C)(=O)=O)c2ccc(C#N)cc2)cc1OC.O=C([O-])[O-]~[Cs+]~[Cs+]>>COc1ccc(OC(CCCN2CC3CN(C(=O)OC(C)(C)C)CC3C2)c2ccc(C#N)cc2)cc1OC | CC#N.CC(C)(C)OC(=O)N1CC2CNCC2C1.COc1ccc(OC(CCCOS(C)(=O)=O)c2ccc(C#N)cc2)cc1OC.O=C([O-])[O-].[Cs+].[Cs+]>>COc1ccc(OC(CCCN2CC3CN(C(=O)OC(C)(C)C)CC3C2)c2ccc(C#N)cc2)cc1OC | US07144914B2_0452grants | e167e792dda8917cf2274aeb0350e7d7bcc61f4dfe4cddaad73f8c71 | CC#N.CS(=O)(=O)O[CH2:11][CH2:10][CH2:9][CH:8]([O:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35]1)[c:27]1[cH:28][cH:29][c:30]([C:31]#[N:32])[cH:33][cH:34]1.O=C([O-])[O-].[Cs+].[Cs+].[NH:12]1[CH2:13][CH:14]2[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH:25]2[CH2:26]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH:14]3[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH:25]3[CH2:26]2)[c:27]2[cH:28][cH:29][c:30]([C:31]#[N:32])[cH:33][cH:34]2)[cH:35][c:36]1[O:37][CH3:38] | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | a320ddb3757b01284fda83a0e3c578c5f2f64f0ce6fab4668551b443 | 0.333333 | 3 | CC#N.O=C([O-])[O-].[Cs+].[Cs+] | 496 |
286,230 | 934,694 | 1,567,759 | [C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3Br)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:22]1(B(O)O)[CH2:24][CH2:23]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].F[B-](F)(F)F.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3[CH:22]3[CH2:24][CH2:23]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2 | |f:2.3.4.5,6.7,10.11.12| | US08933236B2_0415 | 2,015 | Br[c:19]1[c:6]([O:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]4)[CH2:17]2)[CH2:18]3)[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:23]1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)[O-].CC(=O)[O-].Cc1ccccc1.F[B-](F)(F)F.O.O=P([O-])([O-])[O-].OB(O)[CH:20]1[CH2:21][CH2:22]1.[K+].[K+].[K+].[Pd+2]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]4)[CH2:17]2)[CH2:18]3)[c:19]([CH:20]2[CH2:21][CH2:22]2)[cH:23]1 | 0.647146 | C1CCC(P(C2CCCCC2)C2CCCCC2)CC1~F[B-](F)(F)F.CC(=O)[O-]~CC(=O)[O-]~[Pd+2].Cc1ccccc1.N#Cc1ccc(OCC23CC4CC(CC(C4)C2)C3)c(Br)c1.O.O=P([O-])([O-])[O-]~[K+]~[K+]~[K+].OB(O)C1CC1>>N#Cc1ccc(OCC23CC4CC(CC(C4)C2)C3)c(C2CC2)c1 | C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)[O-].CC(=O)[O-].Cc1ccccc1.F[B-](F)(F)F.N#Cc1ccc(OCC23CC4CC(CC(C4)C2)C3)c(Br)c1.O.O=P([O-])([O-])[O-].OB(O)C1CC1.[K+].[K+].[K+].[Pd+2]>>N#Cc1ccc(OCC23CC4CC(CC(C4)C2)C3)c(C2CC2)c1 | US08933236B2_0415grants | db52141692f756e3f1f9cacd8f04cc05216fdac42e51034919c84289 | Br[c:19]1[c:6]([O:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]4)[CH2:17]2)[CH2:18]3)[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:23]1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)[O-].CC(=O)[O-].Cc1ccccc1.F[B-](F)(F)F.O.O=P([O-])([O-])[O-].OB(O)[CH:20]1[CH2:21][CH2:22]1.[K+].[K+].[K+].[Pd+2] | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][C:9]23[CH2:10][CH:11]4[CH2:12][CH:13]([CH2:14][CH:15]([CH2:16]4)[CH2:17]2)[CH2:18]3)[c:19]([CH:20]2[CH2:21][CH2:22]2)[cH:23]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[CH;D3;+0:4]1-[C:5]-[C:6]-1)>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(O-B(-O)-[CH;D3;+0:4]1-[C:5]-[C:6]-1) | 300393a05cebcddeb7b7db9ac083064f2b3fc6d33cbdda0f3e35aac8 | 1 | 1 | C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)[O-].CC(=O)[O-].Cc1ccccc1.F[B-](F)(F)F.O.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd+2] | 956 |
382,417 | 971,378 | null | [C:1]([C:5]1[CH:6]=[C:7]([C:17]2[S:18][CH:19]=[C:20]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:21]=2)[CH:8]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[N:28]1([CH2:33][C:34](O)=[O:35])[CH:32]=[CH:31][N:30]=[CH:29]1>>[C:13]([C:9]1[CH:8]=[C:7]([C:17]2[S:18][CH:19]=[C:20]([CH:22]3[CH2:27][CH2:26][N:25]([C:34](=[O:35])[CH2:33][N:28]4[CH:32]=[CH:31][N:30]=[CH:29]4)[CH2:24][CH2:23]3)[N:21]=2)[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[O:11][CH3:12])([CH3:16])([CH3:15])[CH3:14] | null | US20100286191A1_0563 | 2,010 | O[C:18](=[O:19])[CH2:20][n:21]1[cH:22][cH:23][n:24][cH:25]1.[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10](-[c:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:26][CH2:27]3)[cH:28][s:29]2)[cH:30][c:31]1[C:32]([CH3:33])([CH3:34])[CH3:35]>>[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10](-[c:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:18](=[O:19])[CH2:20][n:21]4[cH:22][cH:23][n:24][cH:25]4)[CH2:26][CH2:27]3)[cH:28][s:29]2)[cH:30][c:31]1[C:32]([CH3:33])([CH3:34])[CH3:35] | 0.155161 | COc1c(C(C)(C)C)cc(-c2nc(C3CCNCC3)cs2)cc1C(C)(C)C.O=C(O)Cn1ccnc1>>COc1c(C(C)(C)C)cc(-c2nc(C3CCN(C(=O)Cn4ccnc4)CC3)cs2)cc1C(C)(C)C | COc1c(C(C)(C)C)cc(-c2nc(C3CCNCC3)cs2)cc1C(C)(C)C.O=C(O)Cn1ccnc1>>COc1c(C(C)(C)C)cc(-c2nc(C3CCN(C(=O)Cn4ccnc4)CC3)cs2)cc1C(C)(C)C | US20100286191A1_0563apps | 7c4ac072d4bd48c37e4ea92d7e4f2354325270fa00dbdeae5df1b4ca | O[C:18](=[O:19])[CH2:20][n:21]1[cH:22][cH:23][n:24][cH:25]1.[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10](-[c:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][NH:17][CH2:26][CH2:27]3)[cH:28][s:29]2)[cH:30][c:31]1[C:32]([CH3:33])([CH3:34])[CH3:35] | [CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10](-[c:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:18](=[O:19])[CH2:20][n:21]4[cH:22][cH:23][n:24][cH:25]4)[CH2:26][CH2:27]3)[cH:28][s:29]2)[cH:30][c:31]1[C:32]([CH3:33])([CH3:34])[CH3:35] | ([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 | null | 146 |
144,555 | 518,823 | 869,698 | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19](I)[CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1.[CH2:26]([N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:27]#[CH:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:28]#[C:27][CH2:26][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1 | null | US07459448B2_1722 | 2,008 | I[c:13]1[cH:12][cH:11][cH:10][c:9]([NH:8][c:7]2[n:6][cH:5][c:4]3[c:24]([n:23]2)-[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][c:31]2[NH:32][C:2](=[O:1])[CH2:3]3)[cH:22]1.[CH:14]#[C:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1>>[O:1]=[C:2]1[CH2:3][c:4]2[cH:5][n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[C:15][CH2:16][N:17]4[CH2:18][CH2:19][CH2:20][CH2:21]4)[cH:22]3)[n:23][c:24]2-[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][c:31]2[NH:32]1 | 0.944451 | C#CCN1CCCC1.O=C1Cc2cnc(Nc3cccc(I)c3)nc2-c2ccc(Cl)cc2N1>>O=C1Cc2cnc(Nc3cccc(C#CCN4CCCC4)c3)nc2-c2ccc(Cl)cc2N1 | C#CCN1CCCC1.O=C1Cc2cnc(Nc3cccc(I)c3)nc2-c2ccc(Cl)cc2N1>>O=C1Cc2cnc(Nc3cccc(C#CCN4CCCC4)c3)nc2-c2ccc(Cl)cc2N1 | US07459448B2_1722grants | b701d62fe87b2724cab9de7ce2a6f899ae3ffa29d71061a4193a6948 | I[c:13]1[cH:12][cH:11][cH:10][c:9]([NH:8][c:7]2[n:6][cH:5][c:4]3[c:24]([n:23]2)-[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][c:31]2[NH:32][C:2](=[O:1])[CH2:3]3)[cH:22]1.[CH:14]#[C:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1 | [O:1]=[C:2]1[CH2:3][c:4]2[cH:5][n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([C:14]#[C:15][CH2:16][N:17]4[CH2:18][CH2:19][CH2:20][CH2:21]4)[cH:22]3)[n:23][c:24]2-[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][c:31]2[NH:32]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 | null | 664 |
57,220 | 244,647 | 412,260 | [C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:19]1(C)[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1P([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1C)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1C.[Br:41][C:42]1[CH:54]=[CH:53][C:52]2C3C(=CC(Br)=CC=3)[C:45]([CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:44]=2[CH:43]=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].C1(C)C=CC=CC=1>[C:8]1([N:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:1]2[CH:2]=[CH:3][C:4]3[C:52]4[C:44](=[CH:43][C:42]([Br:41])=[CH:54][CH:53]=4)[C:45]([CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:5]=3[CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1 | |f:4.5.6| | US05770737_ | 1,998 | Br[c:32]1[cH:31][cH:30][c:29]2[c:47]([cH:46]1)[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[c:22]1[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]1-2.Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li]CCCC.[NH:33]([c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1)[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.[Pd]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[c:22]2[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]2-[c:29]2[cH:30][cH:31][c:32]([N:33]([c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[cH:46][c:47]21 | 0.287815 | CCCCCCCCCCC1(CCCCCCCCCC)c2cc(Br)ccc2-c2ccc(Br)cc21.Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~O=C(/C=C/c1ccccc1)/C=C/c1ccccc1~[Pd].[Li]CCCC.c1ccc(Nc2ccccc2)cc1>>CCCCCCCCCCC1(CCCCCCCCCC)c2cc(Br)ccc2-c2ccc(N(c3ccccc3)c3ccccc3)cc21 | CCCCCCCCCCC1(CCCCCCCCCC)c2cc(Br)ccc2-c2ccc(Br)cc21.Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li]CCCC.[Pd].c1ccc(Nc2ccccc2)cc1>>CCCCCCCCCCC1(CCCCCCCCCC)c2cc(Br)ccc2-c2ccc(N(c3ccccc3)c3ccccc3)cc21 | US05770737_grants | 03793569765c05e5e91e712c2cfc39be6debe1ce3527e4abb2c0ab7e | Br[c:32]1[cH:31][cH:30][c:29]2[c:47]([cH:46]1)[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[c:22]1[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]1-2.Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li]CCCC.[NH:33]([c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1)[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.[Pd] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[c:22]2[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]2-[c:29]2[cH:30][cH:31][c:32]([N:33]([c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[cH:46][c:47]21 | ([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]) | 88813d288b411e9dcd9953025bdcbcaf2f937182f82d770443cabf1d | 0.5 | 2 | Cc1ccccc1.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li]CCCC.[Pd] | 894 |
210,650 | 712,012 | 1,173,028 | [CH3:1][S:2]([CH2:5][CH2:6][N:7]1[CH2:13][CH2:12][C:11]2[CH:14]=[C:15]([NH2:20])[C:16]([O:18][CH3:19])=[CH:17][C:10]=2[CH2:9][CH2:8]1)(=[O:4])=[O:3].Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[CH:31][C:30]=2[O:42][CH3:43])[C:25]([Cl:44])=[CH:24][N:23]=1>>[Cl:44][C:25]1[C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[CH:31][C:30]=2[O:42][CH3:43])=[N:27][C:22]([NH:20][C:15]2[C:16]([O:18][CH3:19])=[CH:17][C:10]3[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:13][CH2:12][C:11]=3[CH:14]=2)=[N:23][CH:24]=1 | null | US08148391B2_3777 | 2,012 | Cl[c:10]1[n:11][cH:12][c:13]([Cl:14])[c:15]([NH:16][c:17]2[cH:18][cH:19][c:20]([N:21]3[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]3)[cH:28][c:29]2[O:30][CH3:31])[n:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH2:9])[CH2:33][CH2:34][N:35]([CH2:36][CH2:37][S:38]([CH3:39])(=[O:40])=[O:41])[CH2:42][CH2:43]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH:9][c:10]1[n:11][cH:12][c:13]([Cl:14])[c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([N:21]4[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]4)[cH:28][c:29]3[O:30][CH3:31])[n:32]1)[CH2:33][CH2:34][N:35]([CH2:36][CH2:37][S:38]([CH3:39])(=[O:40])=[O:41])[CH2:42][CH2:43]2 | 0.648507 | COc1cc(N2CCN(C)CC2)ccc1Nc1nc(Cl)ncc1Cl.COc1cc2c(cc1N)CCN(CCS(C)(=O)=O)CC2>>COc1cc2c(cc1Nc1ncc(Cl)c(Nc3ccc(N4CCN(C)CC4)cc3OC)n1)CCN(CCS(C)(=O)=O)CC2 | COc1cc(N2CCN(C)CC2)ccc1Nc1nc(Cl)ncc1Cl.COc1cc2c(cc1N)CCN(CCS(C)(=O)=O)CC2>>COc1cc2c(cc1Nc1ncc(Cl)c(Nc3ccc(N4CCN(C)CC4)cc3OC)n1)CCN(CCS(C)(=O)=O)CC2 | US08148391B2_3777grants | 7868d5f38276601f13c5a1b2cdde37cf12d947dd7e34e969893fc381 | Cl[c:10]1[n:11][cH:12][c:13]([Cl:14])[c:15]([NH:16][c:17]2[cH:18][cH:19][c:20]([N:21]3[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]3)[cH:28][c:29]2[O:30][CH3:31])[n:32]1.[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH2:9])[CH2:33][CH2:34][N:35]([CH2:36][CH2:37][S:38]([CH3:39])(=[O:40])=[O:41])[CH2:42][CH2:43]2 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[NH:9][c:10]1[n:11][cH:12][c:13]([Cl:14])[c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([N:21]4[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]4)[cH:28][c:29]3[O:30][CH3:31])[n:32]1)[CH2:33][CH2:34][N:35]([CH2:36][CH2:37][S:38]([CH3:39])(=[O:40])=[O:41])[CH2:42][CH2:43]2 | ([#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 | null | 808 |
441,370 | 1,914,611 | null | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:27][C:18]3=[N:19][CH:20]=[CH:21][C:22]([CH2:23][C:24](O)=[O:25])=[C:17]3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[CH2:29][N:30]=[C:31]=NCCCN(C)C.Cl.CNC.CCO>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:27][C:18]3=[N:19][CH:20]=[CH:21][C:22]([CH2:23][C:24]([N:30]([CH3:31])[CH3:29])=[O:25])=[C:17]3[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | |f:1.2| | US20160222005A1_0571 | 2,016 | CCN=C=NCCCN(C)C.CCO.CN(C)c1ccncc1.Cl.ClCCl.O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][c:11]2[nH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[cH:26][cH:27]3)[n:28][c:29]12.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][c:11]2[nH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[cH:26][cH:27]3)[n:28][c:29]12 | 0.607601 | CCN=C=NCCCN(C)C~Cl.CCO.CN(C)c1ccncc1.CNC.ClCCl.O=C(O)Cc1ccnc2[nH]c(-c3ccc(OCc4ccccc4)cc3)nc12>>CN(C)C(=O)Cc1ccnc2[nH]c(-c3ccc(OCc4ccccc4)cc3)nc12 | CCN=C=NCCCN(C)C.CCO.CN(C)c1ccncc1.CNC.Cl.ClCCl.O=C(O)Cc1ccnc2[nH]c(-c3ccc(OCc4ccccc4)cc3)nc12>>CN(C)C(=O)Cc1ccnc2[nH]c(-c3ccc(OCc4ccccc4)cc3)nc12 | US20160222005A1_0571apps | f4bff3a5f89e33d02d6395bf3aa5c28f0a9384601542ee5cc60cc7c3 | CCN=C=NCCCN(C)C.CCO.CN(C)c1ccncc1.Cl.ClCCl.O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][c:11]2[nH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[cH:26][cH:27]3)[n:28][c:29]12.[CH3:1][NH:2][CH3:3] | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][n:10][c:11]2[nH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[cH:26][cH:27]3)[n:28][c:29]12 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CCN=C=NCCCN(C)C.CCO.CN(C)c1ccncc1.Cl.ClCCl | 146 |
408,293 | 1,590,838 | null | Cl.[NH2:2][C:3]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:12]([C:24]([F:27])([F:26])[F:25])[CH:11]=1)([CH2:6][OH:7])[CH2:4][OH:5].C(=O)([O-])O.[Na+].[CH2:33]([O:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C>[CH2:33]([O:40][C:41](=[O:42])[NH:2][C:3]([CH2:4][OH:5])([CH2:6][OH:7])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:12]([C:24]([F:25])([F:26])[F:27])[CH:11]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1 | |f:0.1,2.3| | US20140296183A1_0167 | 2,014 | CCOC(C)=O.Cl.Cl[C:21](=[O:22])[O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.O=C([O-])O.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C:15]([CH2:16][OH:17])([CH2:18][OH:19])[NH2:20])[cH:31][c:32]1[C:33]([F:34])([F:35])[F:36].[Na+]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C:15]([CH2:16][OH:17])([CH2:18][OH:19])[NH:20][C:21](=[O:22])[O:23][CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:31][c:32]1[C:33]([F:34])([F:35])[F:36] | 0.188981 | CCCCCCCOc1ccc(CCC(N)(CO)CO)cc1C(F)(F)F~Cl.CCOC(C)=O.O=C(Cl)OCc1ccccc1.O=C([O-])O~[Na+]>>CCCCCCCOc1ccc(CCC(CO)(CO)NC(=O)OCc2ccccc2)cc1C(F)(F)F | CCCCCCCOc1ccc(CCC(N)(CO)CO)cc1C(F)(F)F.CCOC(C)=O.Cl.O=C(Cl)OCc1ccccc1.O=C([O-])O.[Na+]>>CCCCCCCOc1ccc(CCC(CO)(CO)NC(=O)OCc2ccccc2)cc1C(F)(F)F | US20140296183A1_0167apps | 265a1557c48105d42f08dae590dedd81e4207da1bef2701d346cb1d7 | CCOC(C)=O.Cl.Cl[C:21](=[O:22])[O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.O=C([O-])O.[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C:15]([CH2:16][OH:17])([CH2:18][OH:19])[NH2:20])[cH:31][c:32]1[C:33]([F:34])([F:35])[F:36].[Na+] | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][CH2:14][C:15]([CH2:16][OH:17])([CH2:18][OH:19])[NH:20][C:21](=[O:22])[O:23][CH2:24][c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:31][c:32]1[C:33]([F:34])([F:35])[F:36] | ([C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1)>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1).([C:11]-[NH2;D1;+0:12]) | 0700d9a1d582b4bef1511f9fb181aa1e8ef062a6c336f391def96a74 | 1 | 1 | CCOC(C)=O.Cl.O=C([O-])O.[Na+] | 479 |
355,854 | 557,016 | null | [CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][NH2:23]>>[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:23][CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)=[CH:8][CH:7]=1 | null | US20080070954A1_0331 | 2,008 | O=[CH:11][c:10]1[cH:9][cH:8][c:7]([CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21]1.[NH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[cH:21][cH:22]1 | 0.971952 | COC(=O)C=Cc1ccc(C=O)cc1.NCCc1ccccn1>>COC(=O)C=Cc1ccc(CNCCc2ccccn2)cc1 | COC(=O)C=Cc1ccc(C=O)cc1.NCCc1ccccn1>>COC(=O)C=Cc1ccc(CNCCc2ccccn2)cc1 | US20080070954A1_0331apps | d6aedb70b9a334236483d924e8931e931e235e5e1542375dac01bcfe | O=[CH:11][c:10]1[cH:9][cH:8][c:7]([CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21]1.[NH2:12][CH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[cH:21][cH:22]1 | ([C:3]-[NH;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(O=[CH;D2;+0:1]-[c:2]).([C:3]-[NH2;D1;+0:4]) | f78624bd87f224b709b14a27d6ee712af84642974d7873cf47c74b30 | 1 | 1 | null | 468 |
369,305 | 749,149 | null | [C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:20](OC(=O)C)(=[O:22])[CH3:21]>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:20](=[O:22])[CH3:21])[CH:13]=1)([CH3:4])([CH3:2])[CH3:3] | null | US20090203750A1_0309 | 2,009 | CC(=O)O[C:2]([CH3:1])=[O:3].CN(C)c1ccncc1.ClCCl.[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C@@H:10]2[CH2:11][C@H:12]2[CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C@@H:10]2[CH2:11][C@H:12]2[CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1 | 0.220825 | CC(=O)OC(C)=O.CC(C)(C)OC(=O)NC[C@@H]1C[C@H]1c1cccc(N)c1.CN(C)c1ccncc1.ClCCl>>CC(=O)Nc1cccc([C@@H]2C[C@H]2CNC(=O)OC(C)(C)C)c1 | CC(=O)OC(C)=O.CC(C)(C)OC(=O)NC[C@@H]1C[C@H]1c1cccc(N)c1.CN(C)c1ccncc1.ClCCl>>CC(=O)Nc1cccc([C@@H]2C[C@H]2CNC(=O)OC(C)(C)C)c1 | US20090203750A1_0309apps | c94b732de8abb77118982b76ffb019853d307e2eeef758bbe3153d66 | CC(=O)O[C:2]([CH3:1])=[O:3].CN(C)c1ccncc1.ClCCl.[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C@@H:10]2[CH2:11][C@H:12]2[CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C@@H:10]2[CH2:11][C@H:12]2[CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1 | ([C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | b7e22e0d3d1463b4dc5e2b14e7859b2f12659f363512c586286db1a5 | 1 | 1 | CN(C)c1ccncc1.ClCCl | 6 |
170,728 | 598,715 | 992,175 | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:32]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N>CN(C=O)C>[NH2:32][C:20](=[O:22])[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1 | null | US07745623B2_0647 | 2,010 | CCN=C=NCCCN(C)C.CN(C)C=O.O[C:11]([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1)=[O:13].On1nnc2ccccc21.[NH3:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1 | 0.267944 | CC(C)(C)OC(=O)N(CCC(=O)O)C1CCN(C(=O)OCc2ccccc2)CC1.CCN=C=NCCCN(C)C.CN(C)C=O.N.On1nnc2ccccc21>>CC(C)(C)OC(=O)N(CCC(N)=O)C1CCN(C(=O)OCc2ccccc2)CC1 | CC(C)(C)OC(=O)N(CCC(=O)O)C1CCN(C(=O)OCc2ccccc2)CC1.CCN=C=NCCCN(C)C.CN(C)C=O.N.On1nnc2ccccc21>>CC(C)(C)OC(=O)N(CCC(N)=O)C1CCN(C(=O)OCc2ccccc2)CC1 | US07745623B2_0647grants | 6c5bcc61a39f843bbce90e5a5271b3d9a3c56fd218c9b5ddd4c69b57 | CCN=C=NCCCN(C)C.CN(C)C=O.O[C:11]([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1)=[O:13].On1nnc2ccccc21.[NH3:12] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11]([NH2:12])=[O:13])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28][CH2:29]1 | ([C:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:4])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH3;D0;+0:4]) | cde300289d1caf5bcfdecbb51b23bf034a2afb0ba0fd01708cbdafa5 | 1 | 1 | CCN=C=NCCCN(C)C.CN(C)C=O.On1nnc2ccccc21 | 313 |
377,696 | 892,264 | null | C([O:3][CH:4](OCC)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[CH:9]=[CH:8][C:7]1=[O:18])C.Cl>C(#N)C>[O:18]=[C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[N:6]1[CH2:5][CH:4]=[O:3] | null | US20100144717A1_1053 | 2,010 | CC#N.CCO[CH:13]([CH2:12][n:11]1[c:9](=[O:10])[cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16][c:15]21)[O:14]CC.Cl>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH:13]=[O:14])[c:15]2[cH:16]1 | 0.688233 | CC#N.CCOC(Cn1c(=O)ccc2ccc(C#N)cc21)OCC.Cl>>N#Cc1ccc2ccc(=O)n(CC=O)c2c1 | CC#N.CCOC(Cn1c(=O)ccc2ccc(C#N)cc21)OCC.Cl>>N#Cc1ccc2ccc(=O)n(CC=O)c2c1 | US20100144717A1_1053apps | de552d0e4e4af0acfbc4117d3f583c703d2b5b0634b66cfbb80c714a | CC#N.CCO[CH:13]([CH2:12][n:11]1[c:9](=[O:10])[cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16][c:15]21)[O:14]CC.Cl | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH:13]=[O:14])[c:15]2[cH:16]1 | ([C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:3])>>(C-C-O-[CH;D3;+0:1](-[C:2])-[O;H0;D2;+0:3]-C-C) | c6aa92c1629c5b64400c886935638b7b3f5321965d97c9db33cc5f6f | 1 | 1 | CC#N.Cl | 409 |
154,933 | 551,122 | 922,034 | [O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:37]([OH:39])=[O:38])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([O:27]CC4C=CC=CC=4)=[C:22]([CH2:35][CH3:36])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[NH:3]1.[H][H]>CO.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@@H:18]([C:37]([OH:39])=[O:38])[CH2:19][C:20]3[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[C:22]([CH2:35][CH3:36])[CH:21]=3)=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[NH:3]1 | null | US07582625B2_0824 | 2,009 | CO.[H][H].[Pd].c1ccc(C[O:36][c:35]2[c:3]([CH2:2][CH3:1])[cH:4][c:5]([CH2:6][C@@H:7]([O:8][C:9](=[O:10])[N:11]3[CH2:12][CH2:13][CH:14]([N:15]4[CH2:16][CH2:17][c:18]5[cH:19][cH:20][cH:21][cH:22][c:23]5[NH:24][C:25]4=[O:26])[CH2:27][CH2:28]3)[C:29](=[O:30])[OH:31])[cH:32][c:33]2[CH3:34])cc1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH2:6][C@@H:7]([O:8][C:9](=[O:10])[N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[NH:24][C:25]3=[O:26])[CH2:27][CH2:28]2)[C:29](=[O:30])[OH:31])[cH:32][c:33]([CH3:34])[c:35]1[OH:36] | 0.94429 | CCc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc(C)c1OCc1ccccc1.CO.[H][H].[Pd]>>CCc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc(C)c1O | CCc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc(C)c1OCc1ccccc1.CO.[H][H].[Pd]>>CCc1cc(C[C@@H](OC(=O)N2CCC(N3CCc4ccccc4NC3=O)CC2)C(=O)O)cc(C)c1O | US07582625B2_0824grants | cccaa49dbf25785ae8b7fa24b40c6b8931bd3261e749e5d723d275bc | CO.[H][H].[Pd].c1ccc(C[O:36][c:35]2[c:3]([CH2:2][CH3:1])[cH:4][c:5]([CH2:6][C@@H:7]([O:8][C:9](=[O:10])[N:11]3[CH2:12][CH2:13][CH:14]([N:15]4[CH2:16][CH2:17][c:18]5[cH:19][cH:20][cH:21][cH:22][c:23]5[NH:24][C:25]4=[O:26])[CH2:27][CH2:28]3)[C:29](=[O:30])[OH:31])[cH:32][c:33]2[CH3:34])cc1 | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([CH2:6][C@@H:7]([O:8][C:9](=[O:10])[N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[NH:24][C:25]3=[O:26])[CH2:27][CH2:28]2)[C:29](=[O:30])[OH:31])[cH:32][c:33]([CH3:34])[c:35]1[OH:36] | ([OH;D1;+0:2]-[c:1])>>([c:1]-[O;H0;D2;+0:2]-C-c1:c:c:c:c:c:1) | 5aae93a61569145ed18632d801932cdc99b7a496825e1c5156904263 | 1 | 1 | CO.[H][H].[Pd] | 23 |
372,101 | 801,370 | null | B(Br)(Br)Br.[CH3:5][C@@H:6]1[CH2:10][CH2:9][C@@H:8]([CH3:11])[N:7]1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:21]C)[CH:18]=2)[CH2:13]1>ClCCl.CO>[CH3:5][C@@H:6]1[CH2:10][CH2:9][C@@H:8]([CH3:11])[N:7]1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:21])[CH:18]=2)[CH2:13]1 | null | US20090306052A1_0130 | 2,009 | BrB(Br)Br.CO.C[O:14][c:13]1[cH:12][cH:11][c:10]2[c:16]([cH:15]1)[CH2:17][CH:8]([N:7]1[C@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[CH3:6])[CH2:9]2.ClCCl>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([CH3:6])[N:7]1[CH:8]1[CH2:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[CH2:17]1 | 0.757204 | BrB(Br)Br.CO.COc1ccc2c(c1)CC(N1[C@H](C)CC[C@H]1C)C2.ClCCl>>C[C@@H]1CC[C@@H](C)N1C1Cc2ccc(O)cc2C1 | BrB(Br)Br.CO.COc1ccc2c(c1)CC(N1[C@H](C)CC[C@H]1C)C2.ClCCl>>C[C@@H]1CC[C@@H](C)N1C1Cc2ccc(O)cc2C1 | US20090306052A1_0130apps | 133bcdab6a4da41745b520d1d6f88f76aed12a57067294c17ecfc62f | BrB(Br)Br.CO.C[O:14][c:13]1[cH:12][cH:11][c:10]2[c:16]([cH:15]1)[CH2:17][CH:8]([N:7]1[C@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[CH3:6])[CH2:9]2.ClCCl | [CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([CH3:6])[N:7]1[CH:8]1[CH2:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[CH2:17]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.CO.ClCCl | 48 |
105,081 | 400,705 | 684,764 | [C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:35][C:36](=[NH:47])[CH2:37][S:38]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=[O:40])=[O:39]>ClCCl>[CH:15]1([CH2:14][CH2:13][CH2:12][C@@H:8]([C:9]2[O:11][N:47]=[C:36]([CH2:37][S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)(=[O:40])=[O:39])[N:35]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1 | null | US06897306B2_0626 | 2,005 | ClCCl.O=C(n1ccnc1)n1ccnc1.O=[C:19](O)[C@@H:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[NH:20]=[C:21]([CH2:22][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[NH:32][OH:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@@H:9]([CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[c:19]1[n:20][c:21]([CH2:22][S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32][o:33]1 | 0.183361 | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)C(=O)O.ClCCl.N=C(CS(=O)(=O)c1ccccc1)NO.O=C(n1ccnc1)n1ccnc1>>CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)c1nc(CS(=O)(=O)c2ccccc2)no1 | CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)C(=O)O.ClCCl.N=C(CS(=O)(=O)c1ccccc1)NO.O=C(n1ccnc1)n1ccnc1>>CC(C)(C)OC(=O)C[C@@H](CCCC1CCCCC1)c1nc(CS(=O)(=O)c2ccccc2)no1 | US06897306B2_0626grants | 46390a0520ebeeaa130ce3a4523fd9176774d38b1e92f910e886362c | ClCCl.O=C(n1ccnc1)n1ccnc1.O=[C:19](O)[C@@H:9]([CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[NH:20]=[C:21]([CH2:22][S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[NH:32][OH:33] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@@H:9]([CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[c:19]1[n:20][c:21]([CH2:22][S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32][o:33]1 | ([C:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:1](-[C:2]):[o;H0;D2;+0:7]:[n;H0;D2;+0:6]:1)>>(O-[C;H0;D3;+0:1](=O)-[C:2]).([C:3]-[C;H0;D3;+0:4](=[NH;D1;+0:5])-[NH;D2;+0:6]-[OH;D1;+0:7]) | c823cfc0e8d309d1e109acc8213fed38db45881c7eab736ebe24a3cd | 1 | 1 | ClCCl.O=C(n1ccnc1)n1ccnc1 | 924 |
325,337 | 1,056,513 | 1,793,383 | [CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13]O)[CH2:2][CH:3]=[CH2:4].S(Cl)([Cl:17])=O>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[CH2:13][Cl:17])[CH2:2][CH:3]=[CH2:4] | null | US09409922B2_0169 | 2,016 | O=S(Cl)[Cl:14].O[CH2:13][c:12]1[c:6]([O:5][CH2:4][CH2:3][CH:2]=[CH2:1])[cH:7][cH:8][c:9]([F:10])[cH:11]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[CH2:13][Cl:14] | 0.665336 | C=CCCOc1ccc(F)cc1CO.O=S(Cl)Cl>>C=CCCOc1ccc(F)cc1CCl | C=CCCOc1ccc(F)cc1CO.O=S(Cl)Cl>>C=CCCOc1ccc(F)cc1CCl | US09409922B2_0169grants | 3f80e29040953bc1812ad796272f712f32c4d03dae5641cd93371186 | O=S(Cl)[Cl:14].O[CH2:13][c:12]1[c:6]([O:5][CH2:4][CH2:3][CH:2]=[CH2:1])[cH:7][cH:8][c:9]([F:10])[cH:11]1 | [CH2:1]=[CH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[CH2:13][Cl:14] | ([Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[CH2;D2;+0:2]-[c:3]) | f219a02056b72fb5f0e81082faa1eb7a39fed15ff0ebe5990bb89c68 | 1 | 1 | null | 81 |
344,552 | 384,870 | null | [N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)([O-])=O>CCO.CCOC(C)=O.[Pd]>[N:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:8]2[C:9]3[C:5](=[C:4]([NH2:1])[CH:12]=[CH:11][CH:10]=3)[CH:6]=[N:7]2)=[CH:15][CH:16]=1 | |f:1.2| | US20060199846A1_0401 | 2,006 | CCO.CCOC(C)=O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.[Pd]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | 0.978669 | CCO~CCOC(C)=O.O=[N+]([O-])c1cccc2c1cnn2Cc1ccncc1.[Pd]>>Nc1cccc2c1cnn2Cc1ccncc1 | CCO.CCOC(C)=O.O=[N+]([O-])c1cccc2c1cnn2Cc1ccncc1.[Pd]>>Nc1cccc2c1cnn2Cc1ccncc1 | US20060199846A1_0401apps | 2ab575f126969de282b0221203c3f4f15138c48f7597352688e21cee | CCO.CCOC(C)=O.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.[Pd] | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.CCOC(C)=O.[Pd] | 1 |
313,882 | 1,020,444 | 1,727,233 | C(N(C(C)C)CC)(C)C.[CH3:10][N:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[Cl:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:23][N:22]=[C:21]2[N:31]([CH2:40][C:41](O)=[O:42])[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]=12.Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-]>C(Cl)Cl>[Cl:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:23][N:22]=[C:21]2[N:31]([CH2:40][C:41]([N:14]3[CH2:15][CH2:16][CH2:17][N:11]([CH3:10])[CH2:12][CH2:13]3)=[O:42])[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]=12 | |f:3.4| | US09260381B2_0450 | 2,016 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.O[C:7](=[O:8])[CH2:9][n:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[c:20]([Cl:21])[c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][n:30][c:31]12.[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:32][CH2:33]1.[O-][n+]1ccccc1O>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[CH2:9][n:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[c:20]([Cl:21])[c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][n:30][c:31]23)[CH2:32][CH2:33]1 | 0.649513 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C~Cl.CN1CCCNCC1.ClCCl.O=C(O)Cn1nc(-c2ccccc2)c2c(Cl)c(-c3ccccc3)nnc21.[O-][n+]1ccccc1O>>CN1CCCN(C(=O)Cn2nc(-c3ccccc3)c3c(Cl)c(-c4ccccc4)nnc32)CC1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN1CCCNCC1.Cl.ClCCl.O=C(O)Cn1nc(-c2ccccc2)c2c(Cl)c(-c3ccccc3)nnc21.[O-][n+]1ccccc1O>>CN1CCCN(C(=O)Cn2nc(-c3ccccc3)c3c(Cl)c(-c4ccccc4)nnc32)CC1 | US09260381B2_0450grants | c5b1afa243568035d50496799a46f063657dfede6ead1bdb14e44fa7 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.O[C:7](=[O:8])[CH2:9][n:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[c:20]([Cl:21])[c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[n:29][n:30][c:31]12.[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:32][CH2:33]1.[O-][n+]1ccccc1O | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[CH2:9][n:10]2[n:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[c:20]([Cl:21])[c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][n:30][c:31]23)[CH2:32][CH2:33]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.ClCCl.[O-][n+]1ccccc1O | 146 |
220,793 | 741,575 | 1,221,583 | [NH2:1][CH2:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([O:25][CH3:26])[N:21]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)[C:8]=1[Cl:34])[CH3:6])=[O:4].[CH3:35][O:36][C:37]([NH:39][C:40]1[N:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48](O)=[O:49])=[CH:42][CH:41]=1)=[O:38].ClC1C(COC2C3N=C(OC)N(CC4C=CC=CN=4)C=3C=CC=2)=C(Cl)C=CC=1N(C)C(=O)CNC(=O)CCC1C=CC(C(NCCOC)=O)=CC=1>>[Cl:34][C:8]1[C:9]([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([O:25][CH3:26])[N:21]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:1][C:48](=[O:49])[CH2:47][CH2:46][C:43]1[CH:42]=[CH:41][C:40]([NH:39][C:37](=[O:38])[O:36][CH3:35])=[N:45][CH:44]=1 | null | US08252793B2_0086 | 2,012 | COCCNC(=O)c1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cc1.O[C:12]([CH2:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[n:49][cH:48]1)=[O:13].[NH2:14][CH2:15][C:16](=[O:17])[N:18]([CH3:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[c:25]([CH2:26][O:27][c:28]2[cH:29][cH:30][cH:31][c:32]3[c:33]2[n:34][c:35]([O:36][CH3:37])[n:38]3[CH2:39][c:40]2[cH:41][cH:42][cH:43][cH:44][n:45]2)[c:46]1[Cl:47]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][C:16](=[O:17])[N:18]([CH3:19])[c:20]2[cH:21][cH:22][c:23]([Cl:24])[c:25]([CH2:26][O:27][c:28]3[cH:29][cH:30][cH:31][c:32]4[c:33]3[n:34][c:35]([O:36][CH3:37])[n:38]4[CH2:39][c:40]3[cH:41][cH:42][cH:43][cH:44][n:45]3)[c:46]2[Cl:47])[cH:48][n:49]1 | 0.454862 | COC(=O)Nc1ccc(CCC(=O)O)cn1.COCCNC(=O)c1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cc1.COc1nc2c(OCc3c(Cl)ccc(N(C)C(=O)CN)c3Cl)cccc2n1Cc1ccccn1>>COC(=O)Nc1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cn1 | COC(=O)Nc1ccc(CCC(=O)O)cn1.COCCNC(=O)c1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cc1.COc1nc2c(OCc3c(Cl)ccc(N(C)C(=O)CN)c3Cl)cccc2n1Cc1ccccn1>>COC(=O)Nc1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cn1 | US08252793B2_0086grants | 65313962c7063307e1b11b5d438cdaa5eac0f1e58510d63fa75bd4a0 | COCCNC(=O)c1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cc1.O[C:12]([CH2:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[n:49][cH:48]1)=[O:13].[NH2:14][CH2:15][C:16](=[O:17])[N:18]([CH3:19])[c:20]1[cH:21][cH:22][c:23]([Cl:24])[c:25]([CH2:26][O:27][c:28]2[cH:29][cH:30][cH:31][c:32]3[c:33]2[n:34][c:35]([O:36][CH3:37])[n:38]3[CH2:39][c:40]2[cH:41][cH:42][cH:43][cH:44][n:45]2)[c:46]1[Cl:47] | [CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][C:12](=[O:13])[NH:14][CH2:15][C:16](=[O:17])[N:18]([CH3:19])[c:20]2[cH:21][cH:22][c:23]([Cl:24])[c:25]([CH2:26][O:27][c:28]3[cH:29][cH:30][cH:31][c:32]4[c:33]3[n:34][c:35]([O:36][CH3:37])[n:38]4[CH2:39][c:40]3[cH:41][cH:42][cH:43][cH:44][n:45]3)[c:46]2[Cl:47])[cH:48][n:49]1 | ([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-[NH2;D1;+0:8]) | 09e961e4c21b1adcf2f8d3b116773699ab5020ae114ca5b853caf10a | 1 | 1 | COCCNC(=O)c1ccc(CCC(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4c3nc(OC)n4Cc3ccccn3)c2Cl)cc1 | 133 |
157,049 | 557,392 | 931,093 | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)=[CH:17][C:9]1=2.[NH2:32][CH:33]1[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:30])([F:31])[F:29])=[C:6]([CH:27]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:32][CH:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)=[O:23])=[CH:25][CH:26]=3)=[CH:17][C:9]1=2 | null | US07601716B2_1110 | 2,009 | O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]3[c:17]([cH:18]2)[N:19]([CH2:20][c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32][CH2:33][NH:34]3)[cH:35][cH:36]1.[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[CH2:37][CH2:38]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][c:16]4[c:17]([cH:18]3)[N:19]([CH2:20][c:21]3[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]3[C:28]([F:29])([F:30])[F:31])[CH2:32][CH2:33][NH:34]4)[cH:35][cH:36]2)[CH2:37][CH2:38]1 | 0.237999 | CN1CCC(N)CC1.O=C(O)c1ccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)cc1>>CN1CCC(NC(=O)c2ccc(-c3cnc4c(c3)N(Cc3cc(Cl)ccc3C(F)(F)F)CCN4)cc2)CC1 | CN1CCC(N)CC1.O=C(O)c1ccc(-c2cnc3c(c2)N(Cc2cc(Cl)ccc2C(F)(F)F)CCN3)cc1>>CN1CCC(NC(=O)c2ccc(-c3cnc4c(c3)N(Cc3cc(Cl)ccc3C(F)(F)F)CCN4)cc2)CC1 | US07601716B2_1110grants | 72b694988f61edeceadc08d2e718e617a4e1339105a8f2776a781404 | O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16]3[c:17]([cH:18]2)[N:19]([CH2:20][c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32][CH2:33][NH:34]3)[cH:35][cH:36]1.[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH2:6])[CH2:37][CH2:38]1 | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][c:16]4[c:17]([cH:18]3)[N:19]([CH2:20][c:21]3[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]3[C:28]([F:29])([F:30])[F:31])[CH2:32][CH2:33][NH:34]4)[cH:35][cH:36]2)[CH2:37][CH2:38]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | null | 334 |
241,902 | 805,446 | 1,333,643 | [NH2:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:6]([CH3:17])[C:5](=[O:18])[N:4]2[CH2:19][CH2:20][O:21][C:3]=12.[O:22]1[CH2:25][CH:24]([CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29])[CH2:23]1>N1C=CC=CC=1>[F:16][C:10]1[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=1[NH:8][C:7]1[C:2]([NH:1][S:28]([CH2:27][CH2:26][CH:24]2[CH2:25][O:22][CH2:23]2)(=[O:30])=[O:29])=[C:3]2[O:21][CH2:20][CH2:19][N:4]2[C:5](=[O:18])[C:6]=1[CH3:17] | null | US08466289B2_0404 | 2,013 | Cl[S:15](=[O:16])(=[O:17])[CH2:18][CH2:19][CH:20]1[CH2:21][O:22][CH2:23]1.[CH3:1][c:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[F:12])[c:13]([NH2:14])[c:24]2[n:25]([c:26]1=[O:27])[CH2:28][CH2:29][O:30]2.c1ccncc1>>[CH3:1][c:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[F:12])[c:13]([NH:14][S:15](=[O:16])(=[O:17])[CH2:18][CH2:19][CH:20]2[CH2:21][O:22][CH2:23]2)[c:24]2[n:25]([c:26]1=[O:27])[CH2:28][CH2:29][O:30]2 | 0.7182 | Cc1c(Nc2ccc(I)cc2F)c(N)c2n(c1=O)CCO2.O=S(=O)(Cl)CCC1COC1.c1ccncc1>>Cc1c(Nc2ccc(I)cc2F)c(NS(=O)(=O)CCC2COC2)c2n(c1=O)CCO2 | Cc1c(Nc2ccc(I)cc2F)c(N)c2n(c1=O)CCO2.O=S(=O)(Cl)CCC1COC1.c1ccncc1>>Cc1c(Nc2ccc(I)cc2F)c(NS(=O)(=O)CCC2COC2)c2n(c1=O)CCO2 | US08466289B2_0404grants | cee2a9d3c34ef7119a7ee87739410fecec97ba762b8bdce705bccbca | Cl[S:15](=[O:16])(=[O:17])[CH2:18][CH2:19][CH:20]1[CH2:21][O:22][CH2:23]1.[CH3:1][c:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[F:12])[c:13]([NH2:14])[c:24]2[n:25]([c:26]1=[O:27])[CH2:28][CH2:29][O:30]2.c1ccncc1 | [CH3:1][c:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[F:12])[c:13]([NH:14][S:15](=[O:16])(=[O:17])[CH2:18][CH2:19][CH:20]2[CH2:21][O:22][CH2:23]2)[c:24]2[n:25]([c:26]1=[O:27])[CH2:28][CH2:29][O:30]2 | ([#7;a:5]:[c:6]:[c:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](-[C:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([#7;a:5]:[c:6]:[c:7]-[NH2;D1;+0:8]) | 3bf888044cd77f614c714cddf13915556a9febb0ceeb35a813621a8b | 1 | 1 | c1ccncc1 | 812 |
401,333 | 1,410,820 | null | [Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][C:9](OC)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Li+].[BH4-].Cl>C1COCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1 | |f:1.2| | US20130217680A1_0460 | 2,013 | C1CCOC1.CO[C:11]([CH2:10][c:9]1[c:3]([O:2][CH3:1])[c:4]([Br:5])[cH:6][cH:7][cH:8]1)=[O:12].Cl.[BH4-].[Li+]>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1[CH2:10][CH2:11][OH:12] | 0.797686 | C1CCOC1.COC(=O)Cc1cccc(Br)c1OC.Cl.[BH4-]~[Li+]>>COc1c(Br)cccc1CCO | C1CCOC1.COC(=O)Cc1cccc(Br)c1OC.Cl.[BH4-].[Li+]>>COc1c(Br)cccc1CCO | US20130217680A1_0460apps | 49fadd11095dd2a01cda1984693db28b0f89d731a23350010c4eec23 | C1CCOC1.CO[C:11]([CH2:10][c:9]1[c:3]([O:2][CH3:1])[c:4]([Br:5])[cH:6][cH:7][cH:8]1)=[O:12].Cl.[BH4-].[Li+] | [CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][cH:8][c:9]1[CH2:10][CH2:11][OH:12] | ([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 | C1CCOC1.Cl.[BH4-].[Li+] | 343 |
389,692 | 1,117,565 | null | CC([Si](C)(C)[O:6][CH2:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:11]=[C:10]([CH3:20])[N:9]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:20][C:10]1[N:9]=[C:8]([CH2:7][OH:6])[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:11]=1 | |f:1.2| | US20110257198A1_0232 | 2,011 | CC(C)(C)[Si](C)(C)[O:14][CH2:13][c:12]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:4][cH:3][c:2]([CH3:1])[n:15]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([CH2:13][OH:14])[n:15]1 | 0.913062 | CCCC[N+](CCCC)(CCCC)CCCC~[F-].Cc1ccc(-c2ccccc2)c(CO[Si](C)(C)C(C)(C)C)n1>>Cc1ccc(-c2ccccc2)c(CO)n1 | CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccc(-c2ccccc2)c(CO[Si](C)(C)C(C)(C)C)n1.[F-]>>Cc1ccc(-c2ccccc2)c(CO)n1 | US20110257198A1_0232apps | 6cdc4c8cb3eea44f6af25d662e253fbf376b4a85f2e439456735b244 | CC(C)(C)[Si](C)(C)[O:14][CH2:13][c:12]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:4][cH:3][c:2]([CH3:1])[n:15]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-] | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([CH2:13][OH:14])[n:15]1 | ([C:2]-[OH;D1;+0:1])>>(C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]) | 368b3f927702b41932c1075690d6eeba50254e115711ea09825c0c9c | 1 | 1 | CCCC[N+](CCCC)(CCCC)CCCC.[F-] | 708 |
102,912 | 393,972 | 673,170 | C([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH:26][C:27]([NH2:29])=[NH:28])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>CO.O>[NH:26]([O:25][CH2:24][CH2:23][O:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[N:13]([CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:5][C:4]([OH:30])=[O:3])[CH:14]=[CH:15]2)[C:27]([NH2:29])=[NH:28] | |f:1.2,4.5| | US06855722B2_00447 | 2,005 | CC[O:21][C:19]([CH2:18][CH:17]([n:16]1[c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][NH:4][C:2](=[NH:1])[NH2:3])[cH:28][c:13]2[cH:14][cH:15]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:20].CO.Cl.O.[Li+].[OH-]>>[NH:1]=[C:2]([NH2:3])[NH:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][cH:15][n:16]2[CH:17]([CH2:18][C:19](=[O:20])[OH:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1 | 0.669848 | CCOC(=O)CC(c1ccccc1)n1ccc2cc(OCCONC(=N)N)ccc21.CO~O.Cl.[Li+]~[OH-]>>N=C(N)NOCCOc1ccc2c(ccn2C(CC(=O)O)c2ccccc2)c1 | CCOC(=O)CC(c1ccccc1)n1ccc2cc(OCCONC(=N)N)ccc21.CO.Cl.O.[Li+].[OH-]>>N=C(N)NOCCOc1ccc2c(ccn2C(CC(=O)O)c2ccccc2)c1 | US06855722B2_00447grants | fbc2ac92fee9eb1aaa7d18d6ff413bf35b022a755e7d64c9162b0dec | CC[O:21][C:19]([CH2:18][CH:17]([n:16]1[c:12]2[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][O:5][NH:4][C:2](=[NH:1])[NH2:3])[cH:28][c:13]2[cH:14][cH:15]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)=[O:20].CO.Cl.O.[Li+].[OH-] | [NH:1]=[C:2]([NH2:3])[NH:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][cH:15][n:16]2[CH:17]([CH2:18][C:19](=[O:20])[OH:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | CO.Cl.O.[Li+].[OH-] | 7 |
407,467 | 1,571,309 | null | C[O:2][C:3]1[C:12]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[C:6]([O:13]C)=[CH:5][C:4]=1[C:15](=[O:25])[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:12]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[C:6]([OH:13])=[CH:5][C:4]=1[C:15](=[O:25])[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18] | null | US20140243349A1_1900 | 2,014 | BrB(Br)Br.C[O:9][c:8]1[cH:7][c:6]([C:4]([CH2:3][C:2](=[O:1])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)=[O:5])[c:12]([O:13]C)[c:11]2[c:10]1[O:17][CH2:16][CH2:15][O:14]2.ClCCl>>[O:1]=[C:2]([CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]2[c:11]([c:12]1[OH:13])[O:14][CH2:15][CH2:16][O:17]2)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | 0.82462 | BrB(Br)Br.COc1cc(C(=O)CC(=O)c2ccccc2)c(OC)c2c1OCCO2.ClCCl>>O=C(CC(=O)c1cc(O)c2c(c1O)OCCO2)c1ccccc1 | BrB(Br)Br.COc1cc(C(=O)CC(=O)c2ccccc2)c(OC)c2c1OCCO2.ClCCl>>O=C(CC(=O)c1cc(O)c2c(c1O)OCCO2)c1ccccc1 | US20140243349A1_1900apps | 9ce76765dabd6a16bfce642a27e012c7b7203f90282717c91aad3dbd | BrB(Br)Br.C[O:9][c:8]1[cH:7][c:6]([C:4]([CH2:3][C:2](=[O:1])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)=[O:5])[c:12]([O:13]C)[c:11]2[c:10]1[O:17][CH2:16][CH2:15][O:14]2.ClCCl | [O:1]=[C:2]([CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]2[c:11]([c:12]1[OH:13])[O:14][CH2:15][CH2:16][O:17]2)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | ([OH;D1;+0:1]-[c:2].[OH;D1;+0:3]-[c:4])>>(C-[O;H0;D2;+0:1]-[c:2].C-[O;H0;D2;+0:3]-[c:4]) | d1f5fe893669d3e53b2812239ed33bc7f23228b96208d35ecd887e17 | 0 | 1 | BrB(Br)Br.ClCCl | 20 |
36,886 | 166,469 | 266,954 | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N+:33]([O-:35])=[O:34])[CH2:14][CH2:15]2)=[CH:6][CH:7]=1 | null | US05190959_ | 1,993 | Cl[CH2:13][CH2:12][CH2:11][O:10][c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1.[NH:14]1[CH2:15][CH2:16][CH:17]([O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1 | 0.804684 | Clc1ccc(C(OC2CCNCC2)c2ccccc2)cc1.O=[N+]([O-])c1ccccc1OCCCCl>>O=[N+]([O-])c1ccccc1OCCCN1CCC(OC(c2ccccc2)c2ccc(Cl)cc2)CC1 | Clc1ccc(C(OC2CCNCC2)c2ccccc2)cc1.O=[N+]([O-])c1ccccc1OCCCCl>>O=[N+]([O-])c1ccccc1OCCCN1CCC(OC(c2ccccc2)c2ccc(Cl)cc2)CC1 | US05190959_grants | a622e380106e6f351b0442d84c8db59c2be403a76e6fb31494f42a73 | Cl[CH2:13][CH2:12][CH2:11][O:10][c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1.[NH:14]1[CH2:15][CH2:16][CH:17]([O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([O:18][CH:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]2)[CH2:33][CH2:34]1 | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(Cl-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | c38df6bb72f417e54d2346e687e032ed86554f208af48effa9422912 | 0.5 | 2 | null | 138 |
297,374 | 967,645 | 1,628,928 | [CH:1]([C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)[CH:6]=[CH:5][C:4]=1[CH2:14][C:15]([OH:17])=O)=[CH2:2].Cl.[N:19]1([CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]3[C:31](=[O:34])[O:32][CH2:33][C:29]=3[CH:28]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH:1]([C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)[CH:6]=[CH:5][C:4]=1[CH2:14][C:15]([N:22]1[CH2:23][CH2:24][N:19]([CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]3[C:31](=[O:34])[O:32][CH2:33][C:29]=3[CH:28]=2)[CH2:20][CH2:21]1)=[O:17])=[CH2:2] | |f:1.2| | US09056859B2_0754 | 2,015 | Cl.ClCCCl.ClCCl.O[C:15]([CH2:14][c:13]1[c:3]([CH:2]=[CH2:1])[cH:4][c:5](-[n:6]2[cH:7][n:8][n:9][n:10]2)[cH:11][cH:12]1)=[O:16].On1nnc2ccccc21.[NH:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[CH2:29][O:30][C:31]3=[O:32])[CH2:33][CH2:34]1>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5](-[n:6]2[cH:7][n:8][n:9][n:10]2)[cH:11][cH:12][c:13]1[CH2:14][C:15](=[O:16])[N:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[CH2:29][O:30][C:31]3=[O:32])[CH2:33][CH2:34]1 | 0.903786 | C=Cc1cc(-n2cnnn2)ccc1CC(=O)O.ClCCCl.ClCCl.Cl~O=C1OCc2cc(CCN3CCNCC3)ccc21.On1nnc2ccccc21>>C=Cc1cc(-n2cnnn2)ccc1CC(=O)N1CCN(CCc2ccc3c(c2)COC3=O)CC1 | C=Cc1cc(-n2cnnn2)ccc1CC(=O)O.Cl.ClCCCl.ClCCl.O=C1OCc2cc(CCN3CCNCC3)ccc21.On1nnc2ccccc21>>C=Cc1cc(-n2cnnn2)ccc1CC(=O)N1CCN(CCc2ccc3c(c2)COC3=O)CC1 | US09056859B2_0754grants | 8f0d13de98dcd626e6f5f69f690ae41acc22d5ada527be9c24efbe9e | Cl.ClCCCl.ClCCl.O[C:15]([CH2:14][c:13]1[c:3]([CH:2]=[CH2:1])[cH:4][c:5](-[n:6]2[cH:7][n:8][n:9][n:10]2)[cH:11][cH:12]1)=[O:16].On1nnc2ccccc21.[NH:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[CH2:29][O:30][C:31]3=[O:32])[CH2:33][CH2:34]1 | [CH2:1]=[CH:2][c:3]1[cH:4][c:5](-[n:6]2[cH:7][n:8][n:9][n:10]2)[cH:11][cH:12][c:13]1[CH2:14][C:15](=[O:16])[N:17]1[CH2:18][CH2:19][N:20]([CH2:21][CH2:22][c:23]2[cH:24][cH:25][c:26]3[c:27]([cH:28]2)[CH2:29][O:30][C:31]3=[O:32])[CH2:33][CH2:34]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | Cl.ClCCCl.ClCCl.On1nnc2ccccc21 | 146 |
369,659 | 754,935 | null | Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C.[Li]CCCC>C1(C)C=CC=CC=1.C1COCC1>[N:8]1([C:4]2[CH:3]=[C:2]([B:14]([OH:19])[OH:15])[CH:7]=[CH:6][CH:5]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1 | null | US20090215778A1_0923 | 2,009 | Br[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1.C1CCOC1.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C.Cc1ccccc1.[Li]CCCC>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1 | 0.293116 | Brc1cccc(N2CCOCC2)c1.C1CCOC1.CC(C)OB(OC(C)C)OC(C)C.Cc1ccccc1.[Li]CCCC>>OB(O)c1cccc(N2CCOCC2)c1 | Brc1cccc(N2CCOCC2)c1.C1CCOC1.CC(C)OB(OC(C)C)OC(C)C.Cc1ccccc1.[Li]CCCC>>OB(O)c1cccc(N2CCOCC2)c1 | US20090215778A1_0923apps | 968b6e43c38a373a76de5a40e9b09d52f9ef6e1908fc1456019381e2 | Br[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1.C1CCOC1.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C.Cc1ccccc1.[Li]CCCC | [OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1 | ([OH;D1;+0:5]-[B;H0;D3;+0:4](-[OH;D1;+0:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).(C-C(-C)-O-[B;H0;D3;+0:4](-[O;H0;D2;+0:5]-C(-C)-C)-[O;H0;D2;+0:6]-C(-C)-C) | 74d86d7233bcf8262220a75d40126ae79a22bf9c7f45647c0a609086 | 1 | 1 | C1CCOC1.Cc1ccccc1.[Li]CCCC | 832 |
382,941 | 979,288 | null | [Cl:1][C:2]1[C:3]([N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([C:20]([O:22]C)=[O:21])=[CH:15][CH:16]=3)[NH:11][C:10]2=[S:24])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:3]([N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([C:20]([OH:22])=[O:21])=[CH:15][CH:16]=3)[NH:11][C:10]2=[S:24])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1 | |f:1.2| | US20100298324A1_0094 | 2,010 | CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[n:10](-[c:11]3[n:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19](=[S:20])[nH:21][c:22]2[cH:23]1.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[n:10](-[c:11]3[n:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19](=[S:20])[nH:21][c:22]2[cH:23]1 | 0.942607 | CO.COC(=O)c1ccc2c(=O)n(-c3ncc(Cl)cc3Cl)c(=S)[nH]c2c1.[Na+]~[OH-]>>O=C(O)c1ccc2c(=O)n(-c3ncc(Cl)cc3Cl)c(=S)[nH]c2c1 | CO.COC(=O)c1ccc2c(=O)n(-c3ncc(Cl)cc3Cl)c(=S)[nH]c2c1.[Na+].[OH-]>>O=C(O)c1ccc2c(=O)n(-c3ncc(Cl)cc3Cl)c(=S)[nH]c2c1 | US20100298324A1_0094apps | 360640603dc8228c5ddaa965d8c3aceed6d0d67d409eb706de8b9232 | CO.C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[n:10](-[c:11]3[n:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19](=[S:20])[nH:21][c:22]2[cH:23]1.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[n:10](-[c:11]3[n:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[c:19](=[S:20])[nH:21][c:22]2[cH:23]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 48f3c58ed4b2eb976195200c79ebaafb36d7eb1c6248c7c6424a4457 | 1 | 1 | CO.[Na+].[OH-] | 247 |
137,543 | 498,505 | 838,764 | [C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)CCl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:17]([N:24]1[CH2:29][CH2:28][N:27]([C:14]([C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[O:16])[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1 | null | US07378420B2_0148 | 2,008 | CN(C)c1ccncc1.ClCCCl.ClCCl.O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C:14](=[O:15])[N:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1 | 0.326342 | CC(C)(C)OC(=O)N1CCCC[C@H]1C(=O)O.CN(C)c1ccncc1.ClCCCl.ClCCl.c1ccc(CN2CCNCC2)cc1>>CC(C)(C)OC(=O)N1CCCC[C@H]1C(=O)N1CCN(Cc2ccccc2)CC1 | CC(C)(C)OC(=O)N1CCCC[C@H]1C(=O)O.CN(C)c1ccncc1.ClCCCl.ClCCl.c1ccc(CN2CCNCC2)cc1>>CC(C)(C)OC(=O)N1CCCC[C@H]1C(=O)N1CCN(Cc2ccccc2)CC1 | US07378420B2_0148grants | d898041f252f3da6636a78425ad3f20795b5446e18b9724ab73d1640 | CN(C)c1ccncc1.ClCCCl.ClCCl.O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:15].[NH:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C:14](=[O:15])[N:16]1[CH2:17][CH2:18][N:19]([CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1 | ([#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | f743119ec5b04ab958b5c5c904dac1bb3d606ad97f1184482153e064 | 1 | 1 | CN(C)c1ccncc1.ClCCCl.ClCCl | 685 |
364,435 | 673,797 | null | [F:1][C:2]([F:15])([F:14])[C:3]([C:10]([F:13])([F:12])[F:11])([OH:9])[CH2:4][CH:5]([CH3:8])[CH2:6][OH:7].FC(F)(F)C(C(F)(F)F)(O)[CH2:19][CH2:20][CH2:21][OH:22].C[Li].C([Li])CCC.C(Cl)(=O)C=C.C(Cl)(=O)C(C)=C>>[C:21]([O:7][CH2:6][CH:5]([CH3:8])[CH2:4][C:3]([C:10]([F:11])([F:12])[F:13])([OH:9])[C:2]([F:14])([F:15])[F:1])(=[O:22])[CH:20]=[CH2:19] | null | US20090054700A1_0115 | 2,009 | C=C(C)C(=O)Cl.Cl[C:3]([CH:2]=[CH2:1])=[O:4].OCCCC(O)(C(F)(F)F)C(F)(F)F.[Li]C.[Li]CCCC.[OH:5][CH2:6][CH:7]([CH3:8])[CH2:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19]>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH:7]([CH3:8])[CH2:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19] | 0.049768 | C=C(C)C(=O)Cl.C=CC(=O)Cl.CC(CO)CC(O)(C(F)(F)F)C(F)(F)F.OCCCC(O)(C(F)(F)F)C(F)(F)F.[Li]C.[Li]CCCC>>C=CC(=O)OCC(C)CC(O)(C(F)(F)F)C(F)(F)F | C=C(C)C(=O)Cl.C=CC(=O)Cl.CC(CO)CC(O)(C(F)(F)F)C(F)(F)F.OCCCC(O)(C(F)(F)F)C(F)(F)F.[Li]C.[Li]CCCC>>C=CC(=O)OCC(C)CC(O)(C(F)(F)F)C(F)(F)F | US20090054700A1_0115apps | ac28d25aeb82538801f5d332a5ac0587ec196a147a99cdb7b084c19d | C=C(C)C(=O)Cl.Cl[C:3]([CH:2]=[CH2:1])=[O:4].OCCCC(O)(C(F)(F)F)C(F)(F)F.[Li]C.[Li]CCCC.[OH:5][CH2:6][CH:7]([CH3:8])[CH2:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19] | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH:7]([CH3:8])[CH2:9][C:10]([OH:11])([C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19] | ([C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4]).([C:5]-[OH;D1;+0:6]) | b9bfc61f3efb4c2ed0f8c94b1f8ff3bcfadff4d0806e11446eb27aa5 | 1 | 1 | C=C(C)C(=O)Cl.OCCCC(O)(C(F)(F)F)C(F)(F)F.[Li]C.[Li]CCCC | 320 |
82,093 | 330,600 | 562,243 | [NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11](=[O:13])[NH2:12].[C:14]1([CH2:20][C:21](O)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ON1C2C=CC=CC=2N=N1.OC1C2N=NNC=2C=CC=1>ClCCl.CN(C)C=O>[C:11]([C:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[S:6][C:2]=1[NH:1][C:21](=[O:22])[CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[NH2:12] | null | US06414013B1_ | 2,002 | CN(C)C=O.ClCCl.O[C:7](=[O:8])[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.Oc1cccc2[nH]nnc12.On1nnc2ccccc21.[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[s:16][c:17]2[c:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH:6][C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[s:16][c:17]2[c:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2 | 0.899344 | CN(C)C=O.ClCCl.NC(=O)c1c(N)sc2c1CCCC2.O=C(O)Cc1ccccc1.Oc1cccc2[nH]nnc12.On1nnc2ccccc21>>NC(=O)c1c(NC(=O)Cc2ccccc2)sc2c1CCCC2 | CN(C)C=O.ClCCl.NC(=O)c1c(N)sc2c1CCCC2.O=C(O)Cc1ccccc1.Oc1cccc2[nH]nnc12.On1nnc2ccccc21>>NC(=O)c1c(NC(=O)Cc2ccccc2)sc2c1CCCC2 | US06414013B1_grants | 976dc7e5191f1c6713205883bca8f6382f83e36edd4c5cfe9c6e95c3 | CN(C)C=O.ClCCl.O[C:7](=[O:8])[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.Oc1cccc2[nH]nnc12.On1nnc2ccccc21.[NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH2:6])[s:16][c:17]2[c:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2 | [NH2:1][C:2](=[O:3])[c:4]1[c:5]([NH:6][C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[s:16][c:17]2[c:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2 | ([#16;a:4]:[c:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#16;a:4]:[c:5]-[NH2;D1;+0:6]) | e1b7920dab4bf68a4c6eff1a3d442cff0ab2b6fc5479867504afa24a | 1 | 1 | CN(C)C=O.ClCCl.Oc1cccc2[nH]nnc12.On1nnc2ccccc21 | 882 |
198,084 | 678,090 | 1,119,568 | [Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Li+].[Li+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[O:10][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH3:18])[CH:21]=1)[CH:5]=[O:6] | |f:1.2.3,5.6| | US08034945B2_0333 | 2,011 | CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CN(C)C=O.Cl[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]1.O=C([O-])[O-].[I-].[Li+].[Li+].[OH:9][c:10]1[c:11]([OH:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][c:18]1[Br:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[c:11]([OH:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][c:18]2[Br:19])[cH:20]1 | 0.980956 | CCCC[N+](CCCC)(CCCC)CCCC~[I-].CCOC(C)=O.CN(C)C=O.COc1cccc(CCl)c1.O=C([O-])[O-]~[Li+]~[Li+].O=Cc1cc(O)c(O)c(Br)c1>>COc1cccc(COc2c(O)cc(C=O)cc2Br)c1 | CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CN(C)C=O.COc1cccc(CCl)c1.O=C([O-])[O-].O=Cc1cc(O)c(O)c(Br)c1.[I-].[Li+].[Li+]>>COc1cccc(COc2c(O)cc(C=O)cc2Br)c1 | US08034945B2_0333grants | 1a5b69310ba0619d99382e6aed4ed0b817367d695cde0537996c00a8 | CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CN(C)C=O.Cl[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20]1.O=C([O-])[O-].[I-].[Li+].[Li+].[OH:9][c:10]1[c:11]([OH:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][c:18]1[Br:19] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[c:11]([OH:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][c:18]2[Br:19])[cH:20]1 | ([c:4]-[O;H0;D2;+0:3]-[CH2;D2;+0:1]-[c:2])>>(Cl-[CH2;D2;+0:1]-[c:2]).([OH;D1;+0:3]-[c:4]) | 19ecb0c449632e1a0d99fd6d4c00076fad1615ed07bc86df1499acb5 | 1 | 1 | CCCC[N+](CCCC)(CCCC)CCCC.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[I-].[Li+].[Li+] | 49 |
90,402 | 356,008 | 607,049 | [Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH2:12]([N:14]([CH2:29][CH3:30])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]1[NH:22][C:23]([CH:27]=O)=[C:24]([CH3:26])[CH:25]=1)=[O:20])[CH3:13]>>[CH2:29]([N:14]([CH2:12][CH3:13])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([C:21]1[NH:22][C:23]([CH:27]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[C:24]([CH3:26])[CH:25]=1)=[O:20])[CH3:30] | null | US06573293B2_ | 2,003 | O=[CH:17][c:16]1[c:14]([CH3:15])[cH:13][c:12]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:11])[nH:29]1.[CH2:18]1[C:19](=[O:20])[NH:21][c:22]2[cH:23][cH:24][c:25]([Br:26])[cH:27][c:28]21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([CH3:15])[c:16]([CH:17]=[C:18]2[C:19](=[O:20])[NH:21][c:22]3[cH:23][cH:24][c:25]([Br:26])[cH:27][c:28]32)[nH:29]1 | 0.930933 | CCN(CC)CCCNC(=O)c1cc(C)c(C=O)[nH]1.O=C1Cc2cc(Br)ccc2N1>>CCN(CC)CCCNC(=O)c1cc(C)c(C=C2C(=O)Nc3ccc(Br)cc32)[nH]1 | CCN(CC)CCCNC(=O)c1cc(C)c(C=O)[nH]1.O=C1Cc2cc(Br)ccc2N1>>CCN(CC)CCCNC(=O)c1cc(C)c(C=C2C(=O)Nc3ccc(Br)cc32)[nH]1 | US06573293B2_grants | 532cc13caeac4cad589997cf1859ae69f2d97ebe675d16df15bbf0e7 | O=[CH:17][c:16]1[c:14]([CH3:15])[cH:13][c:12]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:11])[nH:29]1.[CH2:18]1[C:19](=[O:20])[NH:21][c:22]2[cH:23][cH:24][c:25]([Br:26])[cH:27][c:28]21 | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([CH3:15])[c:16]([CH:17]=[C:18]2[C:19](=[O:20])[NH:21][c:22]3[cH:23][cH:24][c:25]([Br:26])[cH:27][c:28]32)[nH:29]1 | ([#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]) | 7924cbf0da79d1713912e854ce0d084a37ce4e2f134b0ab1fff2a499 | 1 | 1 | null | 440 |
312,665 | 1,016,720 | 1,721,254 | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:11]3[CH:21]=[C:20]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[C:19](B4OC(C)(C)C(C)(C)O4)=[CH:18][C:12]=3[C:13]=2[C:14]([NH:16][CH3:17])=[O:15])[CH:6]=[CH:5][N:4]=1.Cl[C:38]1[CH:39]=[CH:40][C:41]2[O:54][CH2:53][N:44]3[C:45]4[CH:46]=[CH:47][CH:48]=[C:49]([F:52])[C:50]=4[CH:51]=[C:43]3[C:42]=2[N:55]=1.C([O-])([O-])=O.[Na+].[Na+].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]>[F:52][C:49]1[C:50]2[CH:51]=[C:43]3[C:42]4[N:55]=[C:38]([C:19]5[C:20]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][C:11]6[O:10][C:9]([C:7]7[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=7)=[C:13]([C:14]([NH:16][CH3:17])=[O:15])[C:12]=6[CH:18]=5)[CH:39]=[CH:40][C:41]=4[O:54][CH2:53][N:44]3[C:45]=2[CH:46]=[CH:47][CH:48]=1 | |f:2.3.4,8.9.10.11.12| | US09242998B2_0158 | 2,016 | C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB([c:25]2[c:18]([N:19]([CH3:20])[S:21]([CH3:22])(=[O:23])=[O:24])[cH:17][c:16]3[o:15][c:6](-[c:7]4[cH:8][cH:9][n:10][c:11]([O:12][CH3:13])[cH:14]4)[c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:45]3[cH:44]2)OC1(C)C.Cl[c:26]1[cH:27][cH:28][c:29]2[c:30]([n:31]1)-[c:32]1[cH:33][c:34]3[c:35]([F:36])[cH:37][cH:38][cH:39][c:40]3[n:41]1[CH2:42][O:43]2.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-].[Na+].[Na+].[Pd].[Pd]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][n:10][c:11]([O:12][CH3:13])[cH:14]2)[o:15][c:16]2[cH:17][c:18]([N:19]([CH3:20])[S:21]([CH3:22])(=[O:23])=[O:24])[c:25](-[c:26]3[cH:27][cH:28][c:29]4[c:30]([n:31]3)-[c:32]3[cH:33][c:34]5[c:35]([F:36])[cH:37][cH:38][cH:39][c:40]5[n:41]3[CH2:42][O:43]4)[cH:44][c:45]12 | 0.740831 | C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CNC(=O)c1c(-c2ccnc(OC)c2)oc2cc(N(C)S(C)(=O)=O)c(B3OC(C)(C)C(C)(C)O3)cc12.Fc1cccc2c1cc1n2COc2ccc(Cl)nc2-1.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-]~[Na+]~[Na+]>>CNC(=O)c1c(-c2ccnc(OC)c2)oc2cc(N(C)S(C)(=O)=O)c(-c3ccc4c(n3)-c3cc5c(F)cccc5n3CO4)cc12 | C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CNC(=O)c1c(-c2ccnc(OC)c2)oc2cc(N(C)S(C)(=O)=O)c(B3OC(C)(C)C(C)(C)O3)cc12.Fc1cccc2c1cc1n2COc2ccc(Cl)nc2-1.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-].[Na+].[Na+].[Pd].[Pd]>>CNC(=O)c1c(-c2ccnc(OC)c2)oc2cc(N(C)S(C)(=O)=O)c(-c3ccc4c(n3)-c3cc5c(F)cccc5n3CO4)cc12 | US09242998B2_0158grants | 15471cd67ecb729a6ad41612966f9f24be79f9f43e0f4bf80c9c7967 | C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CC1(C)OB([c:25]2[c:18]([N:19]([CH3:20])[S:21]([CH3:22])(=[O:23])=[O:24])[cH:17][c:16]3[o:15][c:6](-[c:7]4[cH:8][cH:9][n:10][c:11]([O:12][CH3:13])[cH:14]4)[c:5]([C:3]([NH:2][CH3:1])=[O:4])[c:45]3[cH:44]2)OC1(C)C.Cl[c:26]1[cH:27][cH:28][c:29]2[c:30]([n:31]1)-[c:32]1[cH:33][c:34]3[c:35]([F:36])[cH:37][cH:38][cH:39][c:40]3[n:41]1[CH2:42][O:43]2.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-].[Na+].[Na+].[Pd].[Pd] | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][n:10][c:11]([O:12][CH3:13])[cH:14]2)[o:15][c:16]2[cH:17][c:18]([N:19]([CH3:20])[S:21]([CH3:22])(=[O:23])=[O:24])[c:25](-[c:26]3[cH:27][cH:28][c:29]4[c:30]([n:31]3)-[c:32]3[cH:33][c:34]5[c:35]([F:36])[cH:37][cH:38][cH:39][c:40]5[n:41]3[CH2:42][O:43]4)[cH:44][c:45]12 | ([#7;a:5]:[c;H0;D3;+0:4](:[c:6])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]):[c:3])-O-C-1(-C)-C).(Cl-[c;H0;D3;+0:4](:[#7;a:5]):[c:6]) | c8807ce5dd17ca7cb89059301c440ca25c39c63c4414f0096d0c22f3 | 1 | 1 | 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-].[Na+].[Na+].[Pd].[Pd] | 955 |
394,617 | 1,247,571 | null | [CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=2)[N:8]=[C:7]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=1)=[O:4].C(=O)([O-])O.[Na+]>C(O)C.C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[N:8]=[C:7]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=1)=[O:4] | |f:1.2| | US20120196854A1_0396 | 2,012 | CC(=O)O.CCO.O=C([O-])O.O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]2[n:13][c:7](-[c:8]3[cH:9][cH:10][cH:11][o:12]3)[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]2[cH:19]1.[Fe].[Na+]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:13][c:14]2[cH:15][cH:16][c:17]([NH2:18])[cH:19][c:20]12 | 0.98111 | CC(=O)O.CCO.COC(=O)c1cc(-c2ccco2)nc2ccc([N+](=O)[O-])cc12.O=C([O-])O~[Na+].[Fe]>>COC(=O)c1cc(-c2ccco2)nc2ccc(N)cc12 | CC(=O)O.CCO.COC(=O)c1cc(-c2ccco2)nc2ccc([N+](=O)[O-])cc12.O=C([O-])O.[Fe].[Na+]>>COC(=O)c1cc(-c2ccco2)nc2ccc(N)cc12 | US20120196854A1_0396apps | 36a4c85a68413bfa46d667cc834453353ee513121475587386b78c1c | CC(=O)O.CCO.O=C([O-])O.O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]2[n:13][c:7](-[c:8]3[cH:9][cH:10][cH:11][o:12]3)[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]2[cH:19]1.[Fe].[Na+] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:13][c:14]2[cH:15][cH:16][c:17]([NH2:18])[cH:19][c:20]12 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CC(=O)O.CCO.O=C([O-])O.[Fe].[Na+] | 1 |
112,135 | 421,702 | 718,659 | [CH2:1]([N:3]([CH2:24][CH3:25])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)[CH3:2]>CCOC(C)=O.[Pd]>[NH2:20][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])=[O:23] | null | US07030139B2_0196 | 2,006 | CCOC(C)=O.O=[N+:22]([O-])[c:21]1[c:11]([NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:10][cH:9][c:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[cH:23]1.[Pd]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]([NH2:22])[cH:23]1 | 0.78647 | CCN(CC)C(=O)c1ccc(NCCc2ccccc2)c([N+](=O)[O-])c1.CCOC(C)=O.[Pd]>>CCN(CC)C(=O)c1ccc(NCCc2ccccc2)c(N)c1 | CCN(CC)C(=O)c1ccc(NCCc2ccccc2)c([N+](=O)[O-])c1.CCOC(C)=O.[Pd]>>CCN(CC)C(=O)c1ccc(NCCc2ccccc2)c(N)c1 | US07030139B2_0196grants | e1573358927e4f815eea9f324ef5228b035e7d5a12d6cf3e239cb6cc | CCOC(C)=O.O=[N+:22]([O-])[c:21]1[c:11]([NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:10][cH:9][c:8]([C:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:7])[cH:23]1.[Pd] | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH:12][CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]([NH2:22])[cH:23]1 | ([#7:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:10]:[c:2](-[NH2;D1;+0:1]):[c:3]:[c:4]:[c:5]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C:7](-[#7:8])=[O;D1;H0:9]):[c:10]:1) | 66e5194ce0ee414ce7a56881d10c95e8776842432066942b97e318db | 1 | 1 | CCOC(C)=O.[Pd] | 489 |
411,996 | 1,659,436 | null | I[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:21]([C@:23]1([OH:30])[CH2:27][CH2:26][N:25]([CH3:28])[C:24]1=[O:29])#[CH:22]>>[OH:30][C@@:23]1([C:21]#[C:22][C:2]2[CH:3]=[C:4]([N:8]3[C:12]4=[CH:13][N:14]=[CH:15][CH:16]=[C:11]4[C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:9]3)[CH:5]=[CH:6][CH:7]=2)[CH2:27][CH2:26][N:25]([CH3:28])[C:24]1=[O:29] | null | US20150065482A1_1556 | 2,015 | I[c:12]1[cH:11][cH:10][cH:9][c:8](-[n:7]2[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:29]3[c:24]2[cH:25][n:26][cH:27][cH:28]3)[cH:23]1.[CH:13]#[C:14][C@:15]1([OH:16])[CH2:17][CH2:18][N:19]([CH3:20])[C:21]1=[O:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][n:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[C:14][C@:15]3([OH:16])[CH2:17][CH2:18][N:19]([CH3:20])[C:21]3=[O:22])[cH:23]2)[c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12 | 0.981036 | C#C[C@]1(O)CCN(C)C1=O.COC(=O)c1nn(-c2cccc(I)c2)c2cnccc12>>COC(=O)c1nn(-c2cccc(C#C[C@]3(O)CCN(C)C3=O)c2)c2cnccc12 | C#C[C@]1(O)CCN(C)C1=O.COC(=O)c1nn(-c2cccc(I)c2)c2cnccc12>>COC(=O)c1nn(-c2cccc(C#C[C@]3(O)CCN(C)C3=O)c2)c2cnccc12 | US20150065482A1_1556apps | c16dcbf43e4d200e3134c96abd2c834ec5935f5faf8095db91d00868 | I[c:12]1[cH:11][cH:10][cH:9][c:8](-[n:7]2[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:29]3[c:24]2[cH:25][n:26][cH:27][cH:28]3)[cH:23]1.[CH:13]#[C:14][C@:15]1([OH:16])[CH2:17][CH2:18][N:19]([CH3:20])[C:21]1=[O:22] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][n:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[C:14][C@:15]3([OH:16])[CH2:17][CH2:18][N:19]([CH3:20])[C:21]3=[O:22])[cH:23]2)[c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12 | ([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 | null | 664 |
21,592 | 103,146 | 166,872 | [Cl:1][C:2]1[C:3]([F:12])=[N:4][C:5]([F:11])=[C:6]([Cl:10])[C:7]=1[CH:8]=[O:9].[BH4-].[Na+].Cl>C(O)C>[Cl:10][C:6]1[C:5]([F:11])=[N:4][C:3]([F:12])=[C:2]([Cl:1])[C:7]=1[CH2:8][OH:9] | |f:1.2| | US04701464_ | 1,987 | CCO.Cl.[BH4-].[Na+].[O:1]=[CH:2][c:3]1[c:4]([Cl:5])[c:6]([F:7])[n:8][c:9]([F:10])[c:11]1[Cl:12]>>[OH:1][CH2:2][c:3]1[c:4]([Cl:5])[c:6]([F:7])[n:8][c:9]([F:10])[c:11]1[Cl:12] | 0.880122 | CCO.Cl.O=Cc1c(Cl)c(F)nc(F)c1Cl.[BH4-]~[Na+]>>OCc1c(Cl)c(F)nc(F)c1Cl | CCO.Cl.O=Cc1c(Cl)c(F)nc(F)c1Cl.[BH4-].[Na+]>>OCc1c(Cl)c(F)nc(F)c1Cl | US04701464_grants | f361be7a0d4a7c32634a83189ddf285e28a7e8be2a3a9dfcc573cd65 | CCO.Cl.[BH4-].[Na+].[O:1]=[CH:2][c:3]1[c:4]([Cl:5])[c:6]([F:7])[n:8][c:9]([F:10])[c:11]1[Cl:12] | [OH:1][CH2:2][c:3]1[c:4]([Cl:5])[c:6]([F:7])[n:8][c:9]([F:10])[c:11]1[Cl: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 | CCO.Cl.[BH4-].[Na+] | 356 |
112,153 | 421,747 | 718,704 | [CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([N+:25]([O-])=O)=[C:10]([NH:12][C:13](=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:11]=1)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:25][C:9]1[CH:8]=[CH:7][C:6]([C:4]([N:3]([CH2:1][CH3:2])[CH2:28][CH3:29])=[O:5])=[CH:11][C:10]=1[NH:12][C:13](=[O:24])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=1 | null | US07030139B2_0278 | 2,006 | CCOC(C)=O.O=[N+:25]([O-])[c:24]1[c:12]([NH:11][C:9]([CH2:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:27][cH:26]2)=[O:10])[cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[cH:22][cH:23]1.[Pd]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[cH:22][cH:23][c:24]2[NH2:25])[cH:26][cH:27]1 | 0.587754 | CCOC(C)=O.CCOc1ccc(CC(=O)Nc2cc(C(=O)N(CC)CC)ccc2[N+](=O)[O-])cc1.[Pd]>>CCOc1ccc(CC(=O)Nc2cc(C(=O)N(CC)CC)ccc2N)cc1 | CCOC(C)=O.CCOc1ccc(CC(=O)Nc2cc(C(=O)N(CC)CC)ccc2[N+](=O)[O-])cc1.[Pd]>>CCOc1ccc(CC(=O)Nc2cc(C(=O)N(CC)CC)ccc2N)cc1 | US07030139B2_0278grants | 558de2da5f6103a7d2b738404430a2a51551209dc8be58c3bcbafdc6 | CCOC(C)=O.O=[N+:25]([O-])[c:24]1[c:12]([NH:11][C:9]([CH2:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:27][cH:26]2)=[O:10])[cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[cH:22][cH:23]1.[Pd] | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[NH:11][c:12]2[cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[cH:22][cH:23][c:24]2[NH2:25])[cH:26][cH:27]1 | ([#7:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:10]:[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:[c:10]:1) | 8254c298c2e653a75cb58f66809df0f64971d50d59adb9c9b386ec4f | 1 | 1 | CCOC(C)=O.[Pd] | 28 |
333,614 | 172,605 | null | C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:20])([CH3:19])[CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][C:9]=1[CH2:21][CH2:22][CH2:23]Cl.[N:25]1([C:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][N:32]=2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:20])([CH3:19])[CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][C:9]=1[CH2:21][CH2:22][CH2:23][N:28]1[CH2:29][CH2:30][N:25]([C:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][N:32]=2)[CH2:26][CH2:27]1 | |f:0.1.2| | US20040138230A1_0313 | 2,004 | Cl[CH2:15][CH2:14][CH2:13][c:12]1[c:10]([Cl:11])[cH:9][c:8]2[c:32]([cH:31]1)[C:2]([CH3:1])([CH3:3])[CH2:4][C:5](=[O:6])[NH:7]2.O=C([O-])[O-].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.[Na+].[Na+]>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][c:10]([Cl:11])[c:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([c:20]4[n:21][o:22][c:23]5[cH:24][cH:25][cH:26][cH:27][c:28]45)[CH2:29][CH2:30]3)[cH:31][c:32]21 | 0.811176 | CC1(C)CC(=O)Nc2cc(Cl)c(CCCCl)cc21.O=C([O-])[O-]~[Na+]~[Na+].c1ccc2c(N3CCNCC3)noc2c1>>CC1(C)CC(=O)Nc2cc(Cl)c(CCCN3CCN(c4noc5ccccc45)CC3)cc21 | CC1(C)CC(=O)Nc2cc(Cl)c(CCCCl)cc21.O=C([O-])[O-].[Na+].[Na+].c1ccc2c(N3CCNCC3)noc2c1>>CC1(C)CC(=O)Nc2cc(Cl)c(CCCN3CCN(c4noc5ccccc45)CC3)cc21 | US20040138230A1_0313apps | bf9920f101745265c700ed8efc34b684361c7f50959cae5f088b28ef | Cl[CH2:15][CH2:14][CH2:13][c:12]1[c:10]([Cl:11])[cH:9][c:8]2[c:32]([cH:31]1)[C:2]([CH3:1])([CH3:3])[CH2:4][C:5](=[O:6])[NH:7]2.O=C([O-])[O-].[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[n:21][o:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.[Na+].[Na+] | [CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][c:10]([Cl:11])[c:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([c:20]4[n:21][o:22][c:23]5[cH:24][cH:25][cH:26][cH:27][c:28]45)[CH2:29][CH2:30]3)[cH:31][c:32]21 | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(Cl-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | c38df6bb72f417e54d2346e687e032ed86554f208af48effa9422912 | 0.5 | 2 | O=C([O-])[O-].[Na+].[Na+] | 138 |
249,517 | 828,088 | 1,372,915 | [H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([OH:18])([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH3:20]>C1COCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([O:18][CH3:20])([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5] | |f:0.1| | US08546434B2_0393 | 2,013 | C1CCOC1.I[CH3:1].[H-].[Na+].[OH:2][C:3]([CH3:4])([CH3:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[OH:17]>>[CH3:1][O:2][C:3]([CH3:4])([CH3:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[OH:17] | 0.265795 | C1CCOC1.CC(C)(C)OC(=O)N[C@@H](C(=O)O)C(C)(C)O.CI.[H-]~[Na+]>>COC(C)(C)[C@@H](NC(=O)OC(C)(C)C)C(=O)O | C1CCOC1.CC(C)(C)OC(=O)N[C@@H](C(=O)O)C(C)(C)O.CI.[H-].[Na+]>>COC(C)(C)[C@@H](NC(=O)OC(C)(C)C)C(=O)O | US08546434B2_0393grants | 1203f7f36addc0d5cbaebed590097fe82cddbd7db15e0620fd4be604 | C1CCOC1.I[CH3:1].[H-].[Na+].[OH:2][C:3]([CH3:4])([CH3:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[OH:17] | [CH3:1][O:2][C:3]([CH3:4])([CH3:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:15](=[O:16])[OH:17] | ([C:2]-[O;H0;D2;+0:3]-[CH3;D1;+0:1])>>(I-[CH3;D1;+0:1]).([C:2]-[OH;D1;+0:3]) | 3f112fb289bac1f05b1a74f7afd73d0dad9ae0e80c6f59107df8cdb1 | 1 | 1 | C1CCOC1.[H-].[Na+] | 140 |
14,695 | 72,826 | 119,744 | [Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]([CH3:17])([CH3:16])[C:13](=[O:15])[CH3:14])=[CH:6][CH:5]=1>>[Br:1][CH2:14][C:13](=[O:15])[C:12]([CH3:17])([CH3:16])[CH2:11][S:10][C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1 | null | US04451281_ | 1,984 | Br[Br:16].[CH3:1][C:2]([CH3:3])([CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=[O:14])[CH3:15]>>[CH3:1][C:2]([CH3:3])([CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=[O:14])[CH2:15][Br:16] | 0.369372 | BrBr.CC(=O)C(C)(C)CSc1ccc(Cl)cc1>>CC(C)(CSc1ccc(Cl)cc1)C(=O)CBr | BrBr.CC(=O)C(C)(C)CSc1ccc(Cl)cc1>>CC(C)(CSc1ccc(Cl)cc1)C(=O)CBr | US04451281_grants | 85d12189b7295bf47e0a09187ecb51ab1ed16631812dc3cc6b51a08f | Br[Br:16].[CH3:1][C:2]([CH3:3])([CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=[O:14])[CH3:15] | [CH3:1][C:2]([CH3:3])([CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[C:13](=[O:14])[CH2:15][Br:16] | ([Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]=[O;D1;H0:4])>>(Br-[Br;H0;D1;+0:1]).([CH3;D1;+0:2]-[C:3]=[O;D1;H0:4]) | 862534fb1c3f9b8172ec7458cd0e86e7917f68b8214063887c9c7d9e | 1 | 1 | null | 173 |
218,664 | 734,995 | 1,211,123 | [NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:19]([O-])=O>C(O)C.[Pt]=O>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[NH2:1])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=1)=[O:7] | null | US08222248B2_1166 | 2,012 | CCO.O=[N+:15]([O-])[c:14]1[c:12]([NH2:13])[cH:11][cH:10][c:9]([C:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:18]([CH3:19])[cH:17]2)=[O:8])[cH:16]1.O=[Pt]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:14]([NH2:15])[cH:16]2)[cH:17][c:18]1[CH3:19] | 0.962529 | CCO.Cc1ccc(NC(=O)c2ccc(N)c([N+](=O)[O-])c2)cc1C.O=[Pt]>>Cc1ccc(NC(=O)c2ccc(N)c(N)c2)cc1C | CCO.Cc1ccc(NC(=O)c2ccc(N)c([N+](=O)[O-])c2)cc1C.O=[Pt]>>Cc1ccc(NC(=O)c2ccc(N)c(N)c2)cc1C | US08222248B2_1166grants | 1b52da4108a0b49f22d37070a10b802707b087c8e206c0f2c20cfee6 | CCO.O=[N+:15]([O-])[c:14]1[c:12]([NH2:13])[cH:11][cH:10][c:9]([C:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:18]([CH3:19])[cH:17]2)=[O:8])[cH:16]1.O=[Pt] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:14]([NH2:15])[cH:16]2)[cH:17][c:18]1[CH3:19] | ([#7:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:5]:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:10]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C:7](-[#7:8])=[O;D1;H0:9]):[c:10]:1) | 66e5194ce0ee414ce7a56881d10c95e8776842432066942b97e318db | 1 | 1 | CCO.O=[Pt] | 489 |
102,839 | 393,761 | 672,909 | [NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[S:11]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:45](Cl)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>ClCCl>[CH2:31]([N:10]([CH2:9][CH:6]1[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:45](=[O:52])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:8][CH2:7]1)[S:11]([NH:14][C:15](=[O:30])[C:16]1[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1)(=[O:12])=[O:13])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1 | null | US06852738B2_00198 | 2,005 | CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.[NH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[S:18](=[O:19])(=[O:20])[NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]2)[CH2:38][CH2:39]1>>[O:1]=[C:2]([NH:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[S:18](=[O:19])(=[O:20])[NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]2)[CH2:38][CH2:39]1)[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1 | 0.026242 | CCN(CC)CC.ClCCl.NCC1CCC(CN(Cc2ccccc2)S(=O)(=O)NC(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1ccccc1>>O=C(NCC1CCC(CN(Cc2ccccc2)S(=O)(=O)NC(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1)c1ccccc1 | CCN(CC)CC.ClCCl.NCC1CCC(CN(Cc2ccccc2)S(=O)(=O)NC(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1.O=C(Cl)c1ccccc1>>O=C(NCC1CCC(CN(Cc2ccccc2)S(=O)(=O)NC(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1)c1ccccc1 | US06852738B2_00198grants | ed6b4dd232cfd19071754f38e7d215e0b574f5b010fdb77022b56818 | CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1.[NH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[S:18](=[O:19])(=[O:20])[NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]2)[CH2:38][CH2:39]1 | [O:1]=[C:2]([NH:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[S:18](=[O:19])(=[O:20])[NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]2)[CH2:38][CH2:39]1)[c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 04f622b60f06614bfdc3f8c27947d26b216da996402159ccfe3a0fc7 | 1 | 1 | CCN(CC)CC.ClCCl | 271 |
254,317 | 842,632 | 1,401,900 | Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:27][C:28]1[CH:29]=[C:30]([CH:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)O)[CH:31]=[CH:32][C:33]=1[F:34].C(N(CC)CC)C>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:35]([C:30]1[CH:31]=[CH:32][C:33]([F:34])=[C:28]([F:27])[CH:29]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:11])[CH2:3]2 | |f:0.1| | US08604015B2_0358 | 2,013 | C1CCOC1.CCN(CC)CC.Cl.ClCCCl.O[C:2](=[O:1])[CH:19]1[CH2:20][N:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26]2.On1nnc2ccccc21.[OH:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([F:17])[cH:18]1>>[O:1]=[C:2]([O:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([F:17])[cH:18]1)[CH:19]1[CH2:20][N:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26]2 | 0.714746 | C1CCOC1.CCN(CC)CC.ClCCCl.Cl~O=C(O)C1CN2CCC1CC2.OC(c1ccccc1)c1ccc(F)c(F)c1.On1nnc2ccccc21>>O=C(OC(c1ccccc1)c1ccc(F)c(F)c1)C1CN2CCC1CC2 | C1CCOC1.CCN(CC)CC.Cl.ClCCCl.O=C(O)C1CN2CCC1CC2.OC(c1ccccc1)c1ccc(F)c(F)c1.On1nnc2ccccc21>>O=C(OC(c1ccccc1)c1ccc(F)c(F)c1)C1CN2CCC1CC2 | US08604015B2_0358grants | 3a5da77a149e1b8c660846e9cea6c6c534e324ca64a89dc2b22e8d4a | C1CCOC1.CCN(CC)CC.Cl.ClCCCl.O[C:2](=[O:1])[CH:19]1[CH2:20][N:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26]2.On1nnc2ccccc21.[OH:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([F:17])[cH:18]1 | [O:1]=[C:2]([O:3][CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[c:16]([F:17])[cH:18]1)[CH:19]1[CH2:20][N:21]2[CH2:22][CH2:23][CH:24]1[CH2:25][CH2:26]2 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[C:4])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[OH;D1;+0:5]) | a6871142fd86a88cf89e8dce15586c0c2325bd32f2c5592778c4dcb1 | 1 | 1 | C1CCOC1.CCN(CC)CC.Cl.ClCCCl.On1nnc2ccccc21 | 17 |
147,630 | 528,728 | 886,166 | [N+:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O)([O-:3])=[O:2].[NH3:11]>CO>[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([NH2:11])=[O:9])([O-:3])=[O:2] | null | US07504382B2_0164 | 2,009 | CO.CO[C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9].[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9] | 0.977999 | CO.COC(=O)CCC[N+](=O)[O-].N>>NC(=O)CCC[N+](=O)[O-] | CO.COC(=O)CCC[N+](=O)[O-].N>>NC(=O)CCC[N+](=O)[O-] | US07504382B2_0164grants | 32431e53ac69889b1a7e3470d7841bd328f0aef2c60a0fa7ae894123 | CO.CO[C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9].[NH3:1] | [NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9] | ([C:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:4])=[O;D1;H0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH3;D0;+0:4]) | 32b2d076d42f6c5d0d9e42aaee8ea11f9f6bde1dfbde54d0a3f692c3 | 1 | 1 | CO | 432 |
202,604 | 690,004 | 1,137,968 | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[O:17]1[C:26]2[CH:25]=[C:24]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[CH:22][C:21]=2[O:20][CH2:19][CH2:18]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl>[O:17]1[C:26]2[CH:25]=[C:24]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][N:39]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[CH:7]=[CH:8][C:9]4=[O:16])[CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[CH:22][C:21]=2[O:20][CH2:19][CH2:18]1 | |f:3.4| | US08071592B2_0249 | 2,011 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CO.ClC(Cl)Cl.O=[CH:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][c:39]21.[NH:14]1[CH2:15][CH2:16][CH:17]([N:18]([CH2:19][c:20]2[cH:21][c:22]3[c:23]([cH:24][n:25]2)[O:26][CH2:27][CH2:28][O:29]3)[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]1.[Na+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH:17]([N:18]([CH2:19][c:20]4[cH:21][c:22]5[c:23]([cH:24][n:25]4)[O:26][CH2:27][CH2:28][O:29]5)[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]3)[c:39]2[cH:40]1 | 0.577948 | CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].CC(C)(C)OC(=O)N(Cc1cc2c(cn1)OCCO2)C1CCNCC1.CO.COc1ccc2ccc(=O)n(CC=O)c2c1.ClC(Cl)Cl>>COc1ccc2ccc(=O)n(CCN3CCC(N(Cc4cc5c(cn4)OCCO5)C(=O)OC(C)(C)C)CC3)c2c1 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)(C)OC(=O)N(Cc1cc2c(cn1)OCCO2)C1CCNCC1.CO.COc1ccc2ccc(=O)n(CC=O)c2c1.ClC(Cl)Cl.[Na+]>>COc1ccc2ccc(=O)n(CCN3CCC(N(Cc4cc5c(cn4)OCCO5)C(=O)OC(C)(C)C)CC3)c2c1 | US08071592B2_0249grants | dd0f4f63ae438566fb0896a10b1b601173ab8ebc963413715acedf64 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CO.ClC(Cl)Cl.O=[CH:13][CH2:12][n:11]1[c:9](=[O:10])[cH:8][cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][c:39]21.[NH:14]1[CH2:15][CH2:16][CH:17]([N:18]([CH2:19][c:20]2[cH:21][c:22]3[c:23]([cH:24][n:25]2)[O:26][CH2:27][CH2:28][O:29]3)[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]1.[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][c:9](=[O:10])[n:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH:17]([N:18]([CH2:19][c:20]4[cH:21][c:22]5[c:23]([cH:24][n:25]4)[O:26][CH2:27][CH2:28][O:29]5)[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]3)[c:39]2[cH:40]1 | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(O=[CH;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 1eecabe0173fa39f206a365ccea98e2b763ff157e33c23433b777de4 | 0.5 | 2 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CO.ClC(Cl)Cl.[Na+] | 484 |
441,312 | 1,914,311 | null | [F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([N:22]1[CH2:25][CH:24]([CH2:26][OH:27])[CH2:23]1)=[O:21].C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[C:20]([N:22]1[CH2:23][CH:24]([CH2:26][O:27][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:25]1)=[O:21] | null | US20160222003A1_0786 | 2,016 | CCN(CC)CC.ClCCl.Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([CH2:15][c:16]3[n:17][nH:18][c:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28][c:29]2[F:30])[CH2:31]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([CH2:15][c:16]3[n:17][nH:18][c:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28][c:29]2[F:30])[CH2:31]1 | 0.505752 | CCN(CC)CC.CS(=O)(=O)Cl.ClCCl.O=C(c1cc(Cc2n[nH]c(=O)c3ccccc23)ccc1F)N1CC(CO)C1>>CS(=O)(=O)OCC1CN(C(=O)c2cc(Cc3n[nH]c(=O)c4ccccc34)ccc2F)C1 | CCN(CC)CC.CS(=O)(=O)Cl.ClCCl.O=C(c1cc(Cc2n[nH]c(=O)c3ccccc23)ccc1F)N1CC(CO)C1>>CS(=O)(=O)OCC1CN(C(=O)c2cc(Cc3n[nH]c(=O)c4ccccc34)ccc2F)C1 | US20160222003A1_0786apps | 42f6688482e9a0539ec9d1d2275cde1caf468a30a6b33a934a57a649 | CCN(CC)CC.ClCCl.Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([CH2:15][c:16]3[n:17][nH:18][c:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28][c:29]2[F:30])[CH2:31]1 | [CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([CH2:15][c:16]3[n:17][nH:18][c:19](=[O:20])[c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28][c:29]2[F:30])[CH2:31]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])>>(Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([C:5]-[OH;D1;+0:6]) | 5b2ff2a69fb7bd6a032938e468684773bcc668928b037bbec0ac8335 | 1 | 1 | CCN(CC)CC.ClCCl | 0 |
236,631 | 789,692 | 1,306,512 | [F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:5]=1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>CC#N.O>[CH3:22][O:21][C:19]([N:10]1[CH2:11][CH2:12][CH:13]([C:15]([OH:17])=[O:16])[CH2:14][CH:9]1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:25])([F:26])[F:1])=[CH:24][CH:23]=1)=[O:20] | |f:1.2| | US08415378B2_0463 | 2,013 | CC#N.CCN(CC)CC.COC(C)(C)C.C[O:11][C:9]([CH:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[CH2:12]1)=[O:10].O.[Br-].[Li+]>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1 | 0.2281 | CC#N.CCN(CC)CC.COC(=O)C1CCN(C(=O)OC)C(Cc2ccc(OC(F)(F)F)cc2)C1.COC(C)(C)C.O.[Br-]~[Li+]>>COC(=O)N1CCC(C(=O)O)CC1Cc1ccc(OC(F)(F)F)cc1 | CC#N.CCN(CC)CC.COC(=O)C1CCN(C(=O)OC)C(Cc2ccc(OC(F)(F)F)cc2)C1.COC(C)(C)C.O.[Br-].[Li+]>>COC(=O)N1CCC(C(=O)O)CC1Cc1ccc(OC(F)(F)F)cc1 | US08415378B2_0463grants | 717e174def768160dc08f855cfc36c32614a6015eee98700f3ba37b4 | CC#N.CCN(CC)CC.COC(C)(C)C.C[O:11][C:9]([CH:8]1[CH2:7][CH2:6][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]([CH2:14][c:15]2[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[CH2:12]1)=[O:10].O.[Br-].[Li+] | [CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH:8]([C:9](=[O:10])[OH:11])[CH2:12][CH:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CC#N.CCN(CC)CC.COC(C)(C)C.O.[Br-].[Li+] | 88 |
126,067 | 464,314 | 786,270 | C([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:12]2[CH2:13][CH2:14][CH2:15][CH:9]([NH2:8])[CH2:10][C:11]=2[CH:19]=1 | null | US07217706B2_0374 | 2,007 | CO.[H][H].[Pd].c1ccc(C[NH:11][CH:10]2[CH2:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:14][CH2:13][CH2:12]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH:10]([NH2:11])[CH2:12][CH2:13][CH2:14]2 | 0.990687 | CO.COc1ccc2c(c1)CC(NCc1ccccc1)CCC2.[H][H].[Pd]>>COc1ccc2c(c1)CC(N)CCC2 | CO.COc1ccc2c(c1)CC(NCc1ccccc1)CCC2.[H][H].[Pd]>>COc1ccc2c(c1)CC(N)CCC2 | US07217706B2_0374grants | e122f74fddf5757d955dddd09b4342127ecb2406d48e4c3941cc3a31 | CO.[H][H].[Pd].c1ccc(C[NH:11][CH:10]2[CH2:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[CH2:14][CH2:13][CH2:12]2)cc1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH:10]([NH2:11])[CH2:12][CH2:13][CH2:14]2 | ([C:1]-[NH2;D1;+0:2])>>([C:1]-[NH;D2;+0:2]-C-c1:c:c:c:c:c:1) | 23c7e643c30554121fb51e7f9f681696bc8cd0f4553856f6a06c1912 | 1 | 1 | CO.[H][H].[Pd] | 561 |
61,734 | 260,714 | 441,243 | [NH2:1][CH2:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.[OH-].[Na+].[C:15](O[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].N>O.O1CCOCC1.C>[C:18]([O:17][C:15]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:16])([CH3:21])([CH3:20])[CH3:19] | |f:1.2| | US05922697_ | 1,999 | C.C1COCCO1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].N.O.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19]1.[Na+].[OH-]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19]1 | 0.190232 | C.C1COCCO1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.N.NCc1ccc(O)c(C(=O)O)c1.O.[Na+]~[OH-]>>CC(C)(C)OC(=O)NCc1ccc(O)c(C(=O)O)c1 | C.C1COCCO1.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.N.NCc1ccc(O)c(C(=O)O)c1.O.[Na+].[OH-]>>CC(C)(C)OC(=O)NCc1ccc(O)c(C(=O)O)c1 | US05922697_grants | 0fd3a7b5b3dd718fca43f17f65265c433f00d44666a30adb54ba5658 | C.C1COCCO1.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].N.O.[NH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19]1.[Na+].[OH-] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[c:15]([C:16](=[O:17])[OH:18])[cH:19]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 | C.C1COCCO1.N.O.[Na+].[OH-] | 686 |
293,791 | 956,189 | 1,607,692 | [CH3:1][P:2](=[O:19])([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:4]=1>C(O)C.[Pd]>[CH3:18][P:2]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:4]=1)([CH3:1])=[O:19] | null | US09012462B2_0732 | 2,015 | CCO.O=[N+:17]([O-])[c:16]1[c:7]([S:4]([CH:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[cH:8][c:9]([P:10]([CH3:11])([CH3:12])=[O:13])[cH:14][cH:15]1.[Pd]>>[CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([P:10]([CH3:11])([CH3:12])=[O:13])[cH:14][cH:15][c:16]1[NH2:17] | 0.288973 | CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1[N+](=O)[O-].CCO.[Pd]>>CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1N | CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1[N+](=O)[O-].CCO.[Pd]>>CC(C)S(=O)(=O)c1cc(P(C)(C)=O)ccc1N | US09012462B2_0732grants | f97a4df1469110ba95a654ce0e66365cb38bfd9d9d6011aac429053b | CCO.O=[N+:17]([O-])[c:16]1[c:7]([S:4]([CH:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[cH:8][c:9]([P:10]([CH3:11])([CH3:12])=[O:13])[cH:14][cH:15]1.[Pd] | [CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([P:10]([CH3:11])([CH3:12])=[O:13])[cH:14][cH:15][c:16]1[NH2:17] | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.[Pd] | 1 |
193,820 | 666,093 | 1,101,236 | C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C>Cl.CCO>[OH:6][C@@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:11][CH2:12]1 | null | US07998999B2_0252 | 2,011 | CC(C)(C)[Si](C)(C)[O:11][C@H:10]1[CH2:9][CH2:8][C@@H:7]([N:6]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:12]1.CCO.Cl>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[C@H:7]1[CH2:8][CH2:9][C@@H:10]([OH:11])[CH2:12][CH2:13]1 | 0.935838 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](N2CCCC2=O)CC1.CCO.Cl>>O=C1CCCN1[C@H]1CC[C@@H](O)CC1 | CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H](N2CCCC2=O)CC1.CCO.Cl>>O=C1CCCN1[C@H]1CC[C@@H](O)CC1 | US07998999B2_0252grants | c013e3e2b88f737c1dd9177d2015020ec7d86ec35351b3a4a01fd5b8 | CC(C)(C)[Si](C)(C)[O:11][C@H:10]1[CH2:9][CH2:8][C@@H:7]([N:6]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:12]1.CCO.Cl | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[C@H:7]1[CH2:8][CH2:9][C@@H:10]([OH:11])[CH2:12][CH2:13]1 | ([C:2]-[OH;D1;+0:1])>>(C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]) | 368b3f927702b41932c1075690d6eeba50254e115711ea09825c0c9c | 1 | 1 | CCO.Cl | 708 |
176,303 | 614,269 | 1,018,610 | Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:3]=[CH:4][C:5]=1[F:15])=[O:14] | null | US07807673B2_0760 | 2,010 | Br[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([NH:13][C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[cH:20]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([NH:13][C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[cH:20]1 | 0.102941 | C#C[Si](C)(C)C.O=C(Nc1cc(Br)ccc1F)C(F)(F)F>>C[Si](C)(C)C#Cc1ccc(F)c(NC(=O)C(F)(F)F)c1 | C#C[Si](C)(C)C.O=C(Nc1cc(Br)ccc1F)C(F)(F)F>>C[Si](C)(C)C#Cc1ccc(F)c(NC(=O)C(F)(F)F)c1 | US07807673B2_0760grants | 912c6457a2b1841429d06d387b7c29e2e9583f0c446239880fb68076 | Br[c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([NH:13][C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[cH:20]1.[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6] | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([F:11])[c:12]([NH:13][C:14](=[O:15])[C:16]([F:17])([F:18])[F:19])[cH:20]1 | ([C;D1;H3:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C;D1;H3:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C:8]#[CH;D1;+0:9]) | ff4ca238d37362c68d3aeb62813915e0d9eb5dc61c300308fde5ffdd | 1 | 1 | null | 671 |
398,598 | 1,328,029 | null | [H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[O:13][CH:12]([CH3:14])[CH2:11][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](OCC)=[O:25])=[CH:18][CH:17]=2)[CH2:9]1>C1COCC1>[CH3:14][CH:12]1[O:13][CH:8]([CH3:7])[CH2:9][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:18][CH:17]=2)[CH2:11]1 | |f:0.1.2.3.4.5| | US20130029980A1_0999 | 2,013 | C1CCOC1.CCO[C:12]([CH2:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][N:4]2[CH2:3][CH:2]([CH3:1])[O:19][CH:17]([CH3:18])[CH2:16]2)[cH:15][cH:14]1)=[O:13].[Al+3].[H-].[H-].[H-].[H-].[Li+]>>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][OH:13])[cH:14][cH:15]2)[CH2:16][CH:17]([CH3:18])[O:19]1 | 0.630941 | C1CCOC1.CCOC(=O)CCc1ccc(CN2CC(C)OC(C)C2)cc1.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+]>>CC1CN(Cc2ccc(CCCO)cc2)CC(C)O1 | C1CCOC1.CCOC(=O)CCc1ccc(CN2CC(C)OC(C)C2)cc1.[Al+3].[H-].[H-].[H-].[H-].[Li+]>>CC1CN(Cc2ccc(CCCO)cc2)CC(C)O1 | US20130029980A1_0999apps | d95695c179b06a825ab2414078b9c350e8c30b2bd151662aed426b08 | C1CCOC1.CCO[C:12]([CH2:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][N:4]2[CH2:3][CH:2]([CH3:1])[O:19][CH:17]([CH3:18])[CH2:16]2)[cH:15][cH:14]1)=[O:13].[Al+3].[H-].[H-].[H-].[H-].[Li+] | [CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([CH2:10][CH2:11][CH2:12][OH:13])[cH:14][cH:15]2)[CH2:16][CH:17]([CH3:18])[O:19]1 | ([C:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])>>(C-C-O-[C;H0;D3;+0:1](-[C:2])=[O;H0;D1;+0:3]) | a6631af41b21b01ef30bc6f050ba77f4649f41c184ba7ddaa745a395 | 1 | 1 | C1CCOC1.[Al+3].[H-].[H-].[H-].[H-].[Li+] | 225 |
339,610 | 291,006 | null | [Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12]Br.[C-:14]#[N:15].[K+]>C(O)C.O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:14]#[N:15] | |f:1.2| | US20050234046A1_0861 | 2,005 | Br[CH2:10][c:9]1[cH:8][c:4]([N+:5](=[O:6])[O-:7])[cH:3][c:2]([CH3:1])[c:13]1[Br:14].CCO.O.[C-:11]#[N:12].[K+]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH2:10][C:11]#[N:12])[c:13]1[Br:14] | 0.975999 | CCO.Cc1cc([N+](=O)[O-])cc(CBr)c1Br.O.[C-]#N~[K+]>>Cc1cc([N+](=O)[O-])cc(CC#N)c1Br | CCO.Cc1cc([N+](=O)[O-])cc(CBr)c1Br.O.[C-]#N.[K+]>>Cc1cc([N+](=O)[O-])cc(CC#N)c1Br | US20050234046A1_0861apps | 603f999311ee6ed075b1ae0245e70e1532a29400e5ef4ab9fb5d82c6 | Br[CH2:10][c:9]1[cH:8][c:4]([N+:5](=[O:6])[O-:7])[cH:3][c:2]([CH3:1])[c:13]1[Br:14].CCO.O.[C-:11]#[N:12].[K+] | [CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH2:10][C:11]#[N:12])[c:13]1[Br:14] | ([N;D1;H0:4]#[C;H0;D2;+0:3]-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([C-;H0;D1:3]#[N;D1;H0:4]) | 4a8e4deb0b76c422b41da3d3271fd917779c02f14055dcca93e437bf | 1 | 1 | CCO.O.[K+] | 39 |
126,912 | 466,734 | 790,767 | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12]C)[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6][C:5]2([CH3:16])[CH3:15] | |f:2.3.4.5| | US07226951B2_0571 | 2,007 | C[O:10][c:9]1[c:8]2[c:15]([cH:14][c:12]([Br:13])[cH:11]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7].ClCCl.O.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([Br:13])[cH:14][c:15]21 | 0.61872 | COc1cc(Br)cc2c1C(=O)CCC2(C)C.ClCCl.O.[Al+3]~[Cl-]~[Cl-]~[Cl-]>>CC1(C)CCC(=O)c2c(O)cc(Br)cc21 | COc1cc(Br)cc2c1C(=O)CCC2(C)C.ClCCl.O.[Al+3].[Cl-].[Cl-].[Cl-]>>CC1(C)CCC(=O)c2c(O)cc(Br)cc21 | US07226951B2_0571grants | 98b97acd3fdc542e265c3c16fa861941e5ca89f753d0d2ced3214129 | C[O:10][c:9]1[c:8]2[c:15]([cH:14][c:12]([Br:13])[cH:11]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7].ClCCl.O.[Al+3].[Cl-].[Cl-].[Cl-] | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([Br:13])[cH:14][c:15]21 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | ClCCl.O.[Al+3].[Cl-].[Cl-].[Cl-] | 48 |
179,978 | 625,401 | 1,035,872 | [C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(OCC)C>C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | null | US07851473B2_0563 | 2,010 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([c:8]2[s:7][cH:6][c:5](-[c:4]3[cH:3][cH:2][cH:1][cH:17][cH:16]3)[n:15]2)[CH2:14][CH2:13]1.CCOC(C)=O.CCOCC.Cl>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][s:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15]2)[cH:16][cH:17]1 | 0.756543 | CC(C)(C)OC(=O)N1CCN(c2nc(-c3ccccc3)cs2)CC1.CCOC(C)=O.CCOCC.Cl>>c1ccc(-c2csc(N3CCNCC3)n2)cc1 | CC(C)(C)OC(=O)N1CCN(c2nc(-c3ccccc3)cs2)CC1.CCOC(C)=O.CCOCC.Cl>>c1ccc(-c2csc(N3CCNCC3)n2)cc1 | US07851473B2_0563grants | 28f744377e32f07a31090295b62dfc34ef7f2c5e1a61d120a0059a4c | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][N:9]([c:8]2[s:7][cH:6][c:5](-[c:4]3[cH:3][cH:2][cH:1][cH:17][cH:16]3)[n:15]2)[CH2:14][CH2:13]1.CCOC(C)=O.CCOCC.Cl | [cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][s:7][c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15]2)[cH:16][cH:17]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 | CCOC(C)=O.CCOCC.Cl | 575 |
372,890 | 814,436 | null | B(Br)(Br)Br.[N:5]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[N:8]([C:14]([C:16]1[C:20]3[CH:21]=[CH:22][C:23]([O:25]C)=[CH:24][C:19]=3[S:18][N:17]=1)=[O:15])[CH2:7][CH2:6]2>ClCCl.ClCCCl>[N:5]12[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13]1)[N:8]([C:14]([C:16]1[C:20]3[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=3[S:18][N:17]=1)=[O:15])[CH2:7][CH2:6]2 | null | US20090325939A1_0630 | 2,009 | BrB(Br)Br.C[O:9][c:8]1[cH:7][c:6]2[s:5][n:4][c:3]([C:2](=[O:1])[N:13]3[CH2:14][CH2:15][N:16]4[CH2:17][CH2:18][CH:19]3[CH2:20][CH2:21]4)[c:12]2[cH:11][cH:10]1.ClCCCl.ClCCl>>[O:1]=[C:2]([c:3]1[n:4][s:5][c:6]2[cH:7][c:8]([OH:9])[cH:10][cH:11][c:12]12)[N:13]1[CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]2 | 0.97839 | BrB(Br)Br.COc1ccc2c(C(=O)N3CCN4CCC3CC4)nsc2c1.ClCCCl.ClCCl>>O=C(c1nsc2cc(O)ccc12)N1CCN2CCC1CC2 | BrB(Br)Br.COc1ccc2c(C(=O)N3CCN4CCC3CC4)nsc2c1.ClCCCl.ClCCl>>O=C(c1nsc2cc(O)ccc12)N1CCN2CCC1CC2 | US20090325939A1_0630apps | c0c1e32a43479ec6465333339adb40b9984838ac83146a6f5d6104e3 | BrB(Br)Br.C[O:9][c:8]1[cH:7][c:6]2[s:5][n:4][c:3]([C:2](=[O:1])[N:13]3[CH2:14][CH2:15][N:16]4[CH2:17][CH2:18][CH:19]3[CH2:20][CH2:21]4)[c:12]2[cH:11][cH:10]1.ClCCCl.ClCCl | [O:1]=[C:2]([c:3]1[n:4][s:5][c:6]2[cH:7][c:8]([OH:9])[cH:10][cH:11][c:12]12)[N:13]1[CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21]2 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCCl.ClCCl | 48 |
203,389 | 692,124 | 1,141,292 | [CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | null | US08084442B2_0325 | 2,011 | Br[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C@H:9]([NH2:10])[CH2:17]2)[cH:18][cH:19]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C@H:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17]2)[cH:18][cH:19]1 | 0.701813 | Brc1ccccc1.N[C@H]1CCN(Cc2ccccc2)C1>>c1ccc(CN2CC[C@H](Nc3ccccc3)C2)cc1 | Brc1ccccc1.N[C@H]1CCN(Cc2ccccc2)C1>>c1ccc(CN2CC[C@H](Nc3ccccc3)C2)cc1 | US08084442B2_0325grants | 0ad442931779d364956f4ee06ea73b366c9de7416d0e046bb4ad77c3 | Br[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C@H:9]([NH2:10])[CH2:17]2)[cH:18][cH:19]1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C@H:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17]2)[cH:18][cH:19]1 | ([C:4]-[NH;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]-[NH2;D1;+0:5]) | 88ffcbcc9749b8afd0066ebed43b9106ac95a6b8b871df109fffe83f | 1 | 1 | null | 519 |
416,845 | 1,728,696 | null | [Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[F:10][C:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:14]2[CH2:13][CH2:12][C:11]([F:10])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)=[N:6][CH:7]=1 | |f:1.2,3.4.5| | US20150210681A1_1068 | 2,015 | CN(C)C=O.Cl.Cl[c:11]1[n:12][cH:13][c:14]([Br:15])[cH:16][n:17]1.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([F:7])[CH2:8][CH2:9][NH:10][CH2:18][CH2:19]1.[Cs+].[Cs+]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([F:7])[CH2:8][CH2:9][N:10]([c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][n:17]2)[CH2:18][CH2:19]1 | 0.971076 | CCOC(=O)C1(F)CCNCC1~Cl.CN(C)C=O.Clc1ncc(Br)cn1.O=C([O-])[O-]~[Cs+]~[Cs+]>>CCOC(=O)C1(F)CCN(c2ncc(Br)cn2)CC1 | CCOC(=O)C1(F)CCNCC1.CN(C)C=O.Cl.Clc1ncc(Br)cn1.O=C([O-])[O-].[Cs+].[Cs+]>>CCOC(=O)C1(F)CCN(c2ncc(Br)cn2)CC1 | US20150210681A1_1068apps | 5ead141bd944becc3932f221897c32f809281e5e2ebac72d3acf96da | CN(C)C=O.Cl.Cl[c:11]1[n:12][cH:13][c:14]([Br:15])[cH:16][n:17]1.O=C([O-])[O-].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([F:7])[CH2:8][CH2:9][NH:10][CH2:18][CH2:19]1.[Cs+].[Cs+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([F:7])[CH2:8][CH2:9][N:10]([c:11]2[n:12][cH:13][c:14]([Br:15])[cH:16][n:17]2)[CH2:18][CH2:19]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[#7;a:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | b57905a5bce8517a4e40b0e20794e889407f66a0ae3d7a09e7fbb00e | 1 | 1 | CN(C)C=O.Cl.O=C([O-])[O-].[Cs+].[Cs+] | 36 |
141,164 | 509,384 | 854,631 | [Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[C:10]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([Br:1])[CH:3]=1)(=[O:12])[CH3:11] | null | US07423038B2_0102 | 2,008 | CC(=O)O[C:2]([CH3:1])=[O:3].ClCCl.[NH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([Br:11])[cH:12]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([Br:11])[cH:12]1 | 0.614253 | CC(=O)OC(C)=O.Cc1ccc(N)cc1Br.ClCCl>>CC(=O)Nc1ccc(C)c(Br)c1 | CC(=O)OC(C)=O.Cc1ccc(N)cc1Br.ClCCl>>CC(=O)Nc1ccc(C)c(Br)c1 | US07423038B2_0102grants | f9c3e4477d4038863b149c0120c890ddca040aa12710e8f8b280563a | CC(=O)O[C:2]([CH3:1])=[O:3].ClCCl.[NH2:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([Br:11])[cH:12]1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([Br:11])[cH:12]1 | ([C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | b7e22e0d3d1463b4dc5e2b14e7859b2f12659f363512c586286db1a5 | 1 | 1 | ClCCl | 6 |
308,334 | 1,002,120 | 1,694,575 | [Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:37][CH:38]4[CH2:42][CH2:41][O:40][CH2:39]4)=[C:24]([NH:27][C:28](=[O:36])[CH:29]=[C:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:43]#[N:44])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C:45](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:37][CH:38]4[CH2:42][CH2:41][O:40][CH2:39]4)=[C:24]([NH:27][C:28](=[O:36])[CH:29]=[C:30]4[CH2:35][CH2:34][N:33]([CH3:45])[CH2:32][CH2:31]4)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:43]#[N:44])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1 | |f:1.2.3| | US09187458B2_0653 | 2,015 | CC#N.I[CH3:1].O=C([O-])[O-].[K+].[K+].[NH:2]1[CH2:3][CH2:4][C:5](=[CH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]3[c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]5[cH:22][cH:23][cH:24][cH:25][n:26]5)[c:27]([Cl:28])[cH:29]4)[c:30]([C:31]#[N:32])[cH:33][n:34][c:35]3[cH:36][c:37]2[O:38][CH:39]2[CH2:40][CH2:41][O:42][CH2:43]2)[CH2:44][CH2:45]1>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[CH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]3[c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]5[cH:22][cH:23][cH:24][cH:25][n:26]5)[c:27]([Cl:28])[cH:29]4)[c:30]([C:31]#[N:32])[cH:33][n:34][c:35]3[cH:36][c:37]2[O:38][CH:39]2[CH2:40][CH2:41][O:42][CH2:43]2)[CH2:44][CH2:45]1 | 0.795643 | CC#N.CI.N#Cc1cnc2cc(OC3CCOC3)c(NC(=O)C=C3CCNCC3)cc2c1Nc1ccc(OCc2ccccn2)c(Cl)c1.O=C([O-])[O-]~[K+]~[K+]>>CN1CCC(=CC(=O)Nc2cc3c(Nc4ccc(OCc5ccccn5)c(Cl)c4)c(C#N)cnc3cc2OC2CCOC2)CC1 | CC#N.CI.N#Cc1cnc2cc(OC3CCOC3)c(NC(=O)C=C3CCNCC3)cc2c1Nc1ccc(OCc2ccccn2)c(Cl)c1.O=C([O-])[O-].[K+].[K+]>>CN1CCC(=CC(=O)Nc2cc3c(Nc4ccc(OCc5ccccn5)c(Cl)c4)c(C#N)cnc3cc2OC2CCOC2)CC1 | US09187458B2_0653grants | a97be71001dc3ebc360e60e2daa4fd743b478d89ce2941d27bd6da00 | CC#N.I[CH3:1].O=C([O-])[O-].[K+].[K+].[NH:2]1[CH2:3][CH2:4][C:5](=[CH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]3[c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]5[cH:22][cH:23][cH:24][cH:25][n:26]5)[c:27]([Cl:28])[cH:29]4)[c:30]([C:31]#[N:32])[cH:33][n:34][c:35]3[cH:36][c:37]2[O:38][CH:39]2[CH2:40][CH2:41][O:42][CH2:43]2)[CH2:44][CH2:45]1 | [CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[CH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][c:12]3[c:13]([NH:14][c:15]4[cH:16][cH:17][c:18]([O:19][CH2:20][c:21]5[cH:22][cH:23][cH:24][cH:25][n:26]5)[c:27]([Cl:28])[cH:29]4)[c:30]([C:31]#[N:32])[cH:33][n:34][c:35]3[cH:36][c:37]2[O:38][CH:39]2[CH2:40][CH2:41][O:42][CH2:43]2)[CH2:44][CH2:45]1 | ([C:2]-[N;H0;D3;+0:3](-[C:4])-[CH3;D1;+0:1])>>(I-[CH3;D1;+0:1]).([C:2]-[NH;D2;+0:3]-[C:4]) | 64a6d4910232f1acf64becb85f504144f0b60a2b59776f77c9c8a0ee | 1 | 1 | CC#N.O=C([O-])[O-].[K+].[K+] | 483 |
231,810 | 774,537 | 1,277,341 | [N:1]1([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[O:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[N:4][N:3]=[N:2]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:46][C:47]1[CH:48]=[CH:49][C:50]([Cl:57])=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:52]=1>C(OCC)(=O)C.CN(C=O)C>[Cl:57][C:50]1[CH:49]=[CH:48][C:47]([NH:46][C:11](=[O:13])[CH2:10][O:9][C:8]2[CH:14]=[CH:15][CH:16]=[C:6]([N:1]3[CH:5]=[N:4][N:3]=[N:2]3)[CH:7]=2)=[CH:52][C:51]=1[C:53]([F:54])([F:55])[F:56] | |f:1.2| | US08362017B2_0217 | 2,013 | CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.CN1CCOCC1.Cl.O[C:2](=[O:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[cH:15]1.On1nnc2ccccc21.[NH2:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1>>[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[cH:15]1)[NH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1 | 0.293893 | CCN=C=NCCCN(C)C~Cl.CCOC(C)=O.CN(C)C=O.CN1CCOCC1.Nc1ccc(Cl)c(C(F)(F)F)c1.O=C(O)COc1cccc(-n2cnnn2)c1.On1nnc2ccccc21>>O=C(COc1cccc(-n2cnnn2)c1)Nc1ccc(Cl)c(C(F)(F)F)c1 | CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.CN1CCOCC1.Cl.Nc1ccc(Cl)c(C(F)(F)F)c1.O=C(O)COc1cccc(-n2cnnn2)c1.On1nnc2ccccc21>>O=C(COc1cccc(-n2cnnn2)c1)Nc1ccc(Cl)c(C(F)(F)F)c1 | US08362017B2_0217grants | fe6eba3b62d1cf0a7d652aad480e5f4a5967663568455b214127ba63 | CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.CN1CCOCC1.Cl.O[C:2](=[O:1])[CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[cH:15]1.On1nnc2ccccc21.[NH2:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]1 | [O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[n:10]2[cH:11][n:12][n:13][n:14]2)[cH:15]1)[NH:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[c:22]([C:23]([F:24])([F:25])[F:26])[cH:27]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.CCOC(C)=O.CN(C)C=O.CN1CCOCC1.Cl.On1nnc2ccccc21 | 365 |
200,438 | 684,129 | 1,128,884 | [C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2].[C:24](Cl)(=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27].C(N(CC)C(C)C)(C)C>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:24](=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2] | null | US08058441B2_0210 | 2,011 | C1CCOC1.CCN(C(C)C)C(C)C.Cl[C:10](=[O:11])[CH2:12][CH:13]([CH3:14])[CH3:15].[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:16][c:17]2[C:18]([CH3:19])([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C:27]1([CH3:28])[CH3:29]>>[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]([CH3:19])([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C:27]1([CH3:28])[CH3:29] | 0.47717 | C1CCOC1.CC(=O)N1c2ccc(N)cc2C(C)(c2ccccc2)CC1(C)C.CC(C)CC(=O)Cl.CCN(C(C)C)C(C)C>>CC(=O)N1c2ccc(NC(=O)CC(C)C)cc2C(C)(c2ccccc2)CC1(C)C | C1CCOC1.CC(=O)N1c2ccc(N)cc2C(C)(c2ccccc2)CC1(C)C.CC(C)CC(=O)Cl.CCN(C(C)C)C(C)C>>CC(=O)N1c2ccc(NC(=O)CC(C)C)cc2C(C)(c2ccccc2)CC1(C)C | US08058441B2_0210grants | 96673eb2ebbb7a510737907b5f80bd0f10b4392712a697f6ac038138 | C1CCOC1.CCN(C(C)C)C(C)C.Cl[C:10](=[O:11])[CH2:12][CH:13]([CH3:14])[CH3:15].[CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:16][c:17]2[C:18]([CH3:19])([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C:27]1([CH3:28])[CH3:29] | [CH3:1][C:2](=[O:3])[N:4]1[c:5]2[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]([CH3:19])([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C:27]1([CH3:28])[CH3:29] | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 3c2f9ebaf4afd5ac92b5ac7c3ff0ba51ecfcd4d148a3c3aad01989cb | 1 | 1 | C1CCOC1.CCN(C(C)C)C(C)C | 9 |
442,125 | 1,918,611 | null | [NH2:1][CH2:2][CH:3]([CH:24]([CH3:26])[CH3:25])[CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH3:19])[C:13](=[O:20])[N:12]([CH2:21][CH3:22])[C:11]2=[O:23])=[O:6].[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[C:37]#[N:38])[C:31](O)=[O:32].CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C.[Cl-].[Na+].O>[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[C:37]#[N:38])[C:31]([NH:1][CH2:2][CH:3]([CH:24]([CH3:26])[CH3:25])[CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH3:19])[C:13](=[O:20])[N:12]([CH2:21][CH3:22])[C:11]2=[O:23])=[O:6])=[O:32] | |f:5.6.7| | US20160229814A1_2326 | 2,016 | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.O.O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22]#[N:23])[c:24]([Cl:25])[cH:26]1.[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH2:14][NH2:15])[CH:27]([CH3:28])[CH3:29])[cH:30][cH:31][c:32]2[n:33]([CH2:34][CH3:35])[c:36]1=[O:37].[Cl-].[Na+]>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH2:14][NH:15][C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([C:22]#[N:23])[c:24]([Cl:25])[cH:26]3)[CH:27]([CH3:28])[CH3:29])[cH:30][cH:31][c:32]2[n:33]([CH2:34][CH3:35])[c:36]1=[O:37] | 0.643103 | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.CCn1c(=O)c2cc(NC(=O)CC(CN)C(C)C)ccc2n(CC)c1=O.N#Cc1ccc(C(=O)O)cc1Cl.O~[Cl-]~[Na+]>>CCn1c(=O)c2cc(NC(=O)CC(CNC(=O)c3ccc(C#N)c(Cl)c3)C(C)C)ccc2n(CC)c1=O | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.CCn1c(=O)c2cc(NC(=O)CC(CN)C(C)C)ccc2n(CC)c1=O.N#Cc1ccc(C(=O)O)cc1Cl.O.[Cl-].[Na+]>>CCn1c(=O)c2cc(NC(=O)CC(CNC(=O)c3ccc(C#N)c(Cl)c3)C(C)C)ccc2n(CC)c1=O | US20160229814A1_2326apps | f80a16a1ef0dea5830225bf755fa18c5d829725c1dfd3436e0619bcf | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.O.O[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([C:22]#[N:23])[c:24]([Cl:25])[cH:26]1.[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH2:14][NH2:15])[CH:27]([CH3:28])[CH3:29])[cH:30][cH:31][c:32]2[n:33]([CH2:34][CH3:35])[c:36]1=[O:37].[Cl-].[Na+] | [CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6]2[cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][CH:13]([CH2:14][NH:15][C:16](=[O:17])[c:18]3[cH:19][cH:20][c:21]([C:22]#[N:23])[c:24]([Cl:25])[cH:26]3)[CH:27]([CH3:28])[CH3:29])[cH:30][cH:31][c:32]2[n:33]([CH2:34][CH3:35])[c:36]1=[O:37] | ([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 | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.O.[Cl-].[Na+] | 334 |
198,197 | 678,414 | 1,119,990 | [NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[CH3:24][C:25]1[N:30]=[C:29]([C:31](O)=[O:32])[CH:28]=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH:18]1([C:16]([NH:15][C:13]2[N:14]=[C:9]3[CH:8]=[CH:7][C:6]([O:5][C:4]4[CH:3]=[C:2]([NH:1][C:31]([C:29]5[CH:28]=[CH:27][CH:26]=[C:25]([CH3:24])[N:30]=5)=[O:32])[CH:23]=[CH:22][CH:21]=4)=[N:11][N:10]3[CH:12]=2)=[O:17])[CH2:20][CH2:19]1 | |f:2.3| | US08034812B2_1514 | 2,011 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:32]1)=[O:8].On1nnc2ccccc21.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]3[n:20][c:21]([NH:22][C:23](=[O:24])[CH:25]4[CH2:26][CH2:27]4)[cH:28][n:29]3[n:30]2)[cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][c:19]4[n:20][c:21]([NH:22][C:23](=[O:24])[CH:25]5[CH2:26][CH2:27]5)[cH:28][n:29]4[n:30]3)[cH:31]2)[n:32]1 | 0.872529 | CCN(CC)CC.CCN=C=NCCCN(C)C~Cl.CN(C)C=O.Cc1cccc(C(=O)O)n1.Nc1cccc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)c1.On1nnc2ccccc21>>Cc1cccc(C(=O)Nc2cccc(Oc3ccc4nc(NC(=O)C5CC5)cn4n3)c2)n1 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cc1cccc(C(=O)O)n1.Cl.Nc1cccc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)c1.On1nnc2ccccc21>>Cc1cccc(C(=O)Nc2cccc(Oc3ccc4nc(NC(=O)C5CC5)cn4n3)c2)n1 | US08034812B2_1514grants | 3bbc510ff956bf06ba0a45985d53ccc0f17d9b3afe2b2539699b7e06 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.O[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:32]1)=[O:8].On1nnc2ccccc21.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][c:19]3[n:20][c:21]([NH:22][C:23](=[O:24])[CH:25]4[CH2:26][CH2:27]4)[cH:28][n:29]3[n:30]2)[cH:31]1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][c:19]4[n:20][c:21]([NH:22][C:23](=[O:24])[CH:25]5[CH2:26][CH2:27]5)[cH:28][n:29]4[n:30]3)[cH:31]2)[n:32]1 | ([#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]).([NH2;D1;+0:5]-[c:6]) | cae27f3c4129620b135addf075ea9d8edc0c900ed8eb2ecab0b577d0 | 1 | 1 | CCN(CC)CC.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21 | 548 |
213,232 | 719,130 | 1,183,855 | [CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)C=O.C(N(CC)C(C)C)(C)C.Cl[C:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45]>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:16]3[CH2:22][CH2:21][N:20]([C:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)[CH3:2] | null | US08163763B2_1268 | 2,012 | CCN(C(C)C)C(C)C.CN(C)C=O.Cc1ccccc1.Cl[C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([c:15]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[n:22]2)[CH2:23][CH2:24][NH:25][CH2:32]3)[cH:33][cH:34]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([c:15]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[n:22]2)[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31])[CH2:32]3)[cH:33][cH:34]1 | 0.719091 | CC(C)OC(=O)Cl.CCN(C(C)C)C(C)C.CCNC(=O)Nc1ccc(-c2nc3c(c(N4CCOCC4)n2)CCNC3)cc1.CN(C)C=O.Cc1ccccc1>>CCNC(=O)Nc1ccc(-c2nc3c(c(N4CCOCC4)n2)CCN(C(=O)OC(C)C)C3)cc1 | CC(C)OC(=O)Cl.CCN(C(C)C)C(C)C.CCNC(=O)Nc1ccc(-c2nc3c(c(N4CCOCC4)n2)CCNC3)cc1.CN(C)C=O.Cc1ccccc1>>CCNC(=O)Nc1ccc(-c2nc3c(c(N4CCOCC4)n2)CCN(C(=O)OC(C)C)C3)cc1 | US08163763B2_1268grants | a27e3536b0ce642dc0ad2789e36af4fc7599333681ef705cf666b958 | CCN(C(C)C)C(C)C.CN(C)C=O.Cc1ccccc1.Cl[C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([c:15]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[n:22]2)[CH2:23][CH2:24][NH:25][CH2:32]3)[cH:33][cH:34]1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([c:15]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[n:22]2)[CH2:23][CH2:24][N:25]([C:26](=[O:27])[O:28][CH:29]([CH3:30])[CH3:31])[CH2:32]3)[cH:33][cH:34]1 | ([#8:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | a8ad6d981577e38ffa105f9cec0abb9f8b4d3de801fd8006168b839b | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.Cc1ccccc1 | 219 |
215,630 | 726,003 | 1,196,022 | [C:1]([N:5]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([N:5]1[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2] | null | US08188113B2_0451 | 2,012 | CO.O=[N+:8]([O-])[c:7]1[cH:6][n:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:10][cH:9]1.[H][H].[Pd]>>[CH3:1][C:2]([CH3:3])([CH3:4])[n:5]1[cH:6][c:7]([NH2:8])[cH:9][n:10]1 | 0.567238 | CC(C)(C)n1cc([N+](=O)[O-])cn1.CO.[H][H].[Pd]>>CC(C)(C)n1cc(N)cn1 | CC(C)(C)n1cc([N+](=O)[O-])cn1.CO.[H][H].[Pd]>>CC(C)(C)n1cc(N)cn1 | US08188113B2_0451grants | 58327ead5c3c2b407bcd42974f5f01a7e5d3dbc01bb646dd43b088d8 | CO.O=[N+:8]([O-])[c:7]1[cH:6][n:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[n:10][cH:9]1.[H][H].[Pd] | [CH3:1][C:2]([CH3:3])([CH3:4])[n:5]1[cH:6][c:7]([NH2:8])[cH:9][n:10]1 | ([NH2;D1;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[#7;a:4]:[#7;a:5]:[c:6]:1) | bece654e65ac1f37c15a45408df8a01ab37250629f4cb1b30c202cce | 1 | 1 | CO.[H][H].[Pd] | 628 |
81,906 | 329,947 | 561,230 | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)=[O:7].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:7] | |f:1.2| | US06410538B2_ | 2,002 | CCO.C[O:15][C:13]([c:12]1[cH:11][cH:10][c:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18]2)=[O:8])[cH:17][cH:16]1)=[O:14].[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[cH:18][c:19]1[O:20][CH3:21] | 0.855416 | CCO.COC(=O)c1ccc(C(=O)c2ccc(OC)c(OC)c2)cc1.[Na+]~[OH-]>>COc1ccc(C(=O)c2ccc(C(=O)O)cc2)cc1OC | CCO.COC(=O)c1ccc(C(=O)c2ccc(OC)c(OC)c2)cc1.[Na+].[OH-]>>COc1ccc(C(=O)c2ccc(C(=O)O)cc2)cc1OC | US06410538B2_grants | 542061cd90ac332e6239f8736e06cfe13543f305c8c820167561e50e | CCO.C[O:15][C:13]([c:12]1[cH:11][cH:10][c:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[cH:18]2)=[O:8])[cH:17][cH:16]1)=[O:14].[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17]2)[cH:18][c:19]1[O:20][CH3:21] | ([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 | CCO.[Na+].[OH-] | 247 |
342,161 | 343,949 | null | [N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:21]=[CH:20][C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:13]=3[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25](O)=[O:26]>>[CH3:22][N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([N:17]1[CH2:18][CH2:19][C:13]2[CH:12]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:21]=[CH:20][C:14]=2[CH2:15][CH2:16]1)=[O:26] | null | US20060089347A1_0145 | 2,006 | O[C:7]([C@H:6]1[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]1)=[O:8].[NH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[CH2:28][CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[N:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[CH2:28][CH2:29]1 | 0.705328 | CN1CCC[C@H]1C(=O)O.c1cc2c(cc1OCCCN1CCCCC1)CCNCC2>>CN1CCC[C@H]1C(=O)N1CCc2ccc(OCCCN3CCCCC3)cc2CC1 | CN1CCC[C@H]1C(=O)O.c1cc2c(cc1OCCCN1CCCCC1)CCNCC2>>CN1CCC[C@H]1C(=O)N1CCc2ccc(OCCCN3CCCCC3)cc2CC1 | US20060089347A1_0145apps | 8a2bfba96f288623e1106e02bc894c5b75e250d326581b17eb872a62 | O[C:7]([C@H:6]1[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]1)=[O:8].[NH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[CH2:28][CH2:29]1 | [CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[C:7](=[O:8])[N:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][c:27]2[CH2:28][CH2:29]1 | ([#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | f743119ec5b04ab958b5c5c904dac1bb3d606ad97f1184482153e064 | 1 | 1 | null | 685 |
382,216 | 968,651 | null | [CH:1]1([CH2:4][O:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([N:12]3[CH2:17][CH2:16][CH:15]([NH:18][C:19]4[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=4[N+:26]([O-])=O)[CH2:14][CH2:13]3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.O.NN>C(O)C.CO.[Ni]>[CH:1]1([CH2:4][O:5][C@H:6]2[CH2:7][CH2:8][C@H:9]([N:12]3[CH2:13][CH2:14][CH:15]([NH:18][C:19]4[C:20]([NH2:26])=[CH:21][CH:22]=[C:23]([CH3:25])[CH:24]=4)[CH2:16][CH2:17]3)[CH2:10][CH2:11]2)[CH2:2][CH2:3]1 | |f:1.2| | US20100280071A1_0510 | 2,010 | CCO.CO.NN.O.O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][c:7]1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][CH2:18][CH:19]3[CH2:20][CH2:21]3)[CH2:22][CH2:23]2)[CH2:24][CH2:25]1.[Ni]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C@H:13]3[CH2:14][CH2:15][C@H:16]([O:17][CH2:18][CH:19]4[CH2:20][CH2:21]4)[CH2:22][CH2:23]3)[CH2:24][CH2:25]2)[cH:26]1 | 0.936423 | CCO.CO.Cc1ccc([N+](=O)[O-])c(NC2CCN([C@@H]3CC[C@@H](OCC4CC4)CC3)CC2)c1.NN~O.[Ni]>>Cc1ccc(N)c(NC2CCN([C@@H]3CC[C@@H](OCC4CC4)CC3)CC2)c1 | CCO.CO.Cc1ccc([N+](=O)[O-])c(NC2CCN([C@@H]3CC[C@@H](OCC4CC4)CC3)CC2)c1.NN.O.[Ni]>>Cc1ccc(N)c(NC2CCN([C@@H]3CC[C@@H](OCC4CC4)CC3)CC2)c1 | US20100280071A1_0510apps | 3e81d3f3d5d88f02f8718e21f64a50c2e85564432633029ee0094751 | CCO.CO.NN.O.O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][c:7]1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C@H:13]2[CH2:14][CH2:15][C@H:16]([O:17][CH2:18][CH:19]3[CH2:20][CH2:21]3)[CH2:22][CH2:23]2)[CH2:24][CH2:25]1.[Ni] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C@H:13]3[CH2:14][CH2:15][C@H:16]([O:17][CH2:18][CH:19]4[CH2:20][CH2:21]4)[CH2:22][CH2:23]3)[CH2:24][CH2:25]2)[cH:26]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCO.CO.NN.O.[Ni] | 1 |
419,359 | 1,751,156 | null | [NH2:1][CH2:2][C@H:3]([OH:13])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl.C(#N)C>[Cl:21][CH2:22][C:23]([NH:1][CH2:2][C@H:3]([OH:13])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1)=[O:24] | |f:3.4| | US20150252038A1_2135 | 2,015 | CC#N.CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH2:5][CH2:6][C@H:7]([OH:8])[CH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][CH2:6][C@H:7]([OH:8])[CH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1 | 0.885521 | CC#N~ClCCl.CCN(CC)CC.NC[C@H](O)Cc1cc(Cl)cc(Cl)c1.O=C(Cl)CCl>>O=C(CCl)NC[C@H](O)Cc1cc(Cl)cc(Cl)c1 | CC#N.CCN(CC)CC.ClCCl.NC[C@H](O)Cc1cc(Cl)cc(Cl)c1.O=C(Cl)CCl>>O=C(CCl)NC[C@H](O)Cc1cc(Cl)cc(Cl)c1 | US20150252038A1_2135apps | 521b6d58ce2cd4cc81f0874f02ca0dea68499a19ea636df799358d4c | CC#N.CCN(CC)CC.ClCCl.Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH2:5][CH2:6][C@H:7]([OH:8])[CH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1 | [O:1]=[C:2]([CH2:3][Cl:4])[NH:5][CH2:6][C@H:7]([OH:8])[CH2:9][c:10]1[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:5]-[C:4])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | CC#N.CCN(CC)CC.ClCCl | 45 |
418,760 | 1,746,822 | null | [H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1>CN(C=O)C>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)=[CH:6][CH:5]=1 | |f:0.1| | US20150246902A1_0225 | 2,015 | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:21][cH:20]1.CN(C)C=O.[H-].[Na+].[nH:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]23)[cH:20][cH:21]1 | 0.352718 | CN(C)C=O.Clc1ccc2cc[nH]c2c1.FC(F)(F)c1ccc(CBr)cc1.[H-]~[Na+]>>FC(F)(F)c1ccc(Cn2ccc3ccc(Cl)cc32)cc1 | CN(C)C=O.Clc1ccc2cc[nH]c2c1.FC(F)(F)c1ccc(CBr)cc1.[H-].[Na+]>>FC(F)(F)c1ccc(Cn2ccc3ccc(Cl)cc32)cc1 | US20150246902A1_0225apps | f5f8587d519b204abc7e3aa1b2ceec6aac8df0fb1e7a94317b40e8ab | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:21][cH:20]1.CN(C)C=O.[H-].[Na+].[nH:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12 | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]23)[cH:20][cH:21]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]) | f1bf419bfb17c41694b54b8f85081d16d18d0d9d2b930a8e883972bf | 1 | 1 | CN(C)C=O.[H-].[Na+] | 528 |
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