original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
154,808 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)=[O:12])[CH:7]=1 | O=C(CBr)c1ccoc1 | O=c1ncc(Cl)c[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 5-chloropyrimidin-2-one (587 mg) and crude 3-bromoacetylfuran (2.00 g, ca. 4.5 mmol, based on purity ca. 40% by 1H n.m.r; contaminated with 3-dibromoacetylfuran and diethyl ether) in triethylamine (0.95 ml) and ethanol (25 ml) was stirred at room temperature. After 45 min with solvent was removed and the r... | O=C(Cn1cc(Cl)cnc1=O)c1ccoc1 | null | 31.2 | null |
1,732,771 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:25]=[C:26]([CH:34]([N:36]5[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]5)[CH3:35])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=4)=[O:22])=[CH:16][C:15]=3[F:49])[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3]... | CC(c1cc(NC(=O)Nc2ccc(Oc3ccnc(NC(=O)C4CC4)c3)c(F)c2)cc(C(F)(F)F)c1)N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | Dissolve the compound obtained in Step 1 (230 mg, 0.33 mmol) in DCM (15 mL), add trifluoroacetic acid (400 mg), stir at room temperature for 2 hrs. Remove the volatiles, partition the residue in EtOAc and saturated NaHCO3 solution, and separate the organic layer, dry over anhydrous Na2SO4. Concentrate under reduced pre... | CC(c1cc(NC(=O)Nc2ccc(Oc3ccnc(NC(=O)C4CC4)c3)c(F)c2)cc(C(F)(F)F)c1)N1CCNCC1 | null | 89.4 | null |
590,302 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]([F:25])([F:24])[CH2:20][CH2:21][CH2:22][NH2:23]>>[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])[C:8]([NH:23][CH2:22][CH2:21][CH2:20][C:19]([F:25])([F:24])[F:18])=... | CC(C(=O)Cl)(c1ccccc1)c1ccccc1 | NCCCC(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid, m.p. 82° C. and MS: m/e=336.2 (M+H+) was prepared in accordance with the general method of example 1 from 2,2-diphenylpropionyl chloride and 4,4,4-trifluorobutyl-amine. | CC(C(=O)NCCCC(F)(F)F)(c1ccccc1)c1ccccc1 | null | null | null |
650,147 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][CH:7]=1.[F:24][C:25]([F:32])([F:31])[CH2:26][S:27](Cl)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20]... | COc1ccccc1Oc1ccc(NCc2cccnc2)cc1 | O=S(=O)(Cl)CC(F)(F)F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of N-(4-(2-methoxyphenoxy)phenyl)pyridin-3-ylmethylamine (1.0 equiv.) in 2:1 DCE/Pyridine (0.15 M) was cooled to 0° C. and treated with 2,2,2-trifluoroethanesulfonyl chloride (1.8 equiv.). The mixture was allowed to warm to ambient temperature and stir overnight. The reaction was treated with anhydrous potas... | COc1ccccc1Oc1ccc(N(Cc2cccnc2)S(=O)(=O)CC(F)(F)F)cc1 | null | null | null |
21,736 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [Mg].II.Br[C:5]([CH3:7])=[CH2:6].[CH3:8][C:9]1[CH2:10][CH2:11][CH:12]2[C:18]=1[CH2:17][CH2:16][C:15](=[O:19])[CH2:14][C:13]2=[CH2:20]>O1CCCC1>[OH:19][C:15]1([C:5]([CH3:7])=[CH2:6])[CH2:16][CH2:17][C:18]2[CH:12]([CH2:11][CH2:10][C:9]=2[CH3:8])[C:13](=[CH2:20])[CH2:14]1 | C=C(C)Br | C=C1CC(=O)CCC2=C(C)CCC12 | null | II | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To a Grignard solution, prepared from 1 g of magnesium chips activated with 1 g of iodine, 5 ml of 2-bromopropene and about 100 ml of tetrahydrofuran, were added over 10 minutes 1.76 g of 1-methyl-4-methylen-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene. The mixture was stirred vigorously for 30 minutes, cooled to 0° and tre... | C=C1CC(O)(C(=C)C)CCC2=C(C)CCC12 | null | 76 | null |
1,066,250 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][N:13](C)C)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.Cl.[C:21]([NH:25]N)([CH3:24])([CH3:23])[CH3:22].C(O)C>O>[C:21]([N:25]1[C:4]([C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[Cl:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:12]=[N:13]1)([CH3:24])([CH3:23... | CCOC(=O)C(=CN(C)C)C(=O)c1ccccc1Cl | CC(C)(C)NN | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 2.82 g of ethyl 2-(2-chlorobenzoyl)-3-(N,N-dimethylamino)acrylate (a compound described in JP-A 7-101940), 1.25 g of tert-butylhydrazine hydrochloride and 10 ml of ethanol was heated to reflux for 8 hours. After the reaction mixture was allowed to cool to room temperature, water was poured and the mixture ... | CCOC(=O)c1cnn(C(C)(C)C)c1-c1ccccc1Cl | null | 15.6 | null |
844,826 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([CH3:27])=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([NH2:26])[CH:20]=[CH:19]2.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4... | COc1cc2nccc(Oc3ccc4cc(N)ccc4c3C)c2cc1OC | O=C(Cl)c1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | 6-(6,7-Dimethoxy-quinolin-4-yloxy)-5-methyl-naphthalen-2-ylamine (Step b, 0.100 g, 0.2 mmol), benzoyl chloride (0.04 mL, 0.3 mmol) and K2CO3 (0.116 g, 0.6 mmol) in CH2Cl2 were stirred overnight under inert atmosphere. The reaction was quenched with water and diluted with CH2Cl2. The aqueous layer was extracted 3 times ... | COc1cc2nccc(Oc3ccc4cc(NC(=O)c5ccccc5)ccc4c3C)c2cc1OC | null | null | null |
216,121 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | Br[C:2]([C:5]([CH3:7])=[O:6])([CH3:4])[CH3:3].[NH:8]1[CH:12]=[CH:11][CH:10]=[N:9]1>>[CH3:3][C:2]([N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1)([C:5](=[O:6])[CH3:7])[CH3:4] | CC(=O)C(C)(C)Br | c1cn[nH]c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1 mol of methyl bromoisopropyl ketone is added dropwise at 100° C. to a melt of 4 mols of pyrazole. The reaction mixture is stirred for a further hour. Following customary working up, 2-methyl-2-(pyrazol-1-yl)-butan-3one is obtained in a yield of 70%. | CC(=O)C(C)(C)n1cccn1 | null | 70 | null |
226,940 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CS(O[CH2:15][C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)(=O)=O>COCCO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:15][C@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:5][CH:4]=1 | CC1(C)OC[C@H](COS(C)(=O)=O)O1 | Oc1ccc(F)cc1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To a stirred solution of 2.7 parts of sodium in 50 parts of 2-methoxyethanol were added 13.2 parts of 4-fluorophenol. The whole was stirred for 15 minutes. A solution of 24.8 parts of (-)-(R)-2,2-dimethyl-1,3-dioxolane-4-methanol methanesulfonate (ester) in 70 parts of 2-methoxyethanol was added dropwise quickly. Stirr... | CC1(C)OC[C@H](COc2ccc(F)cc2)O1 | null | 97.3 | null |
1,207,787 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH2:8]Br)[CH:7]=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:25][C:22]2[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20... | COc1c(CBr)cc(Br)cc1C(C)(C)C | O=[N+]([O-])c1ccc(O)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 50 | 2 | step 2—A mixture of 114 (0.20 g, 0.59 mmol), 4-nitrophenol (0.082 g, 0.59 mmol) and K2CO3 (0.12 g, 0.89 mmol) in DMF was stirred at 50° C. for 2 h. The mixture was cooled to RT and partitioned between water and Et2O. The ether layer was concentrated, and the crude residue was purified by SiO2 chromatography eluting wit... | COc1c(COc2ccc([N+](=O)[O-])cc2)cc(Br)cc1C(C)(C)C | null | 81.7 | null |
1,526,836 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | COC(C1C(O)=C(O)N=C(CC2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)CCCC2)N=1)=O.[CH3:25][NH:26][C:27]([C:29]1[N:30]=[C:31]([CH2:37][C:38]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:42][CH2:41][CH2:40][CH2:39]2)[NH:32][C:33](=[O:36])[C:34]=1[OH:35])=[O:28]>>[CH2:25]([NH:26][C:27]([C:29]1[C:34]([OH:35])=[C:3... | COC(=O)c1nc(CC2(c3ccccc3)CCCC2)nc(O)c1O | CNC(=O)c1nc(CC2(c3ccccc3)CCCC2)[nH]c(=O)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5,6-Dihydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid benzylamide was synthesized as an off-white solid (20 mg, 30%) from 55 mg of 5,6-dihydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid methyl ester following the procedure described for 5-hydroxy-6-oxo-2-(1-phenyl-cyclopentylmethy... | O=C(NCc1ccccc1)c1nc(CC2(c3ccccc3)CCCC2)nc(O)c1O | null | null | null |
1,057,796 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][C:2]12[CH:11]([CH:12]=[O:13])[CH2:10][CH2:9][CH:8]=[C:7]1[CH2:6][C:5]1([S:17][CH2:16][CH2:15][S:14]1)[CH2:4][CH2:3]2.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][C:2]12[CH:11]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[OH:13])[CH2:10][CH2:9][CH:8]=[C:7]1[CH2:6][C:5]1([S:14... | Br[Mg]c1ccccc1 | CC12CCC3(CC1=CCCC2C=O)SCCS3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | null | Aldehyde 241 (200 mg, 0.746 mmol) was dissolved in 10 mL THF and cooled to −78° C. Phenylmagnesium bromide (1M in THF, 1.12 mL, 1.12 mmol) was added to the solution dropwise and the mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was then cooled to 0° C. and quenched with 10 mL of wat... | CC12CCC3(CC1=CCCC2C(O)c1ccccc1)SCCS3 | null | 92.8 | null |
1,191,439 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | S(Cl)([Cl:3])=O.[C:5]([OH:15])(=O)[C:6]1[NH:13][C:11](=[O:12])[NH:10][C:8](=[O:9])[CH:7]=1>O>[O:12]=[C:11]1[NH:13][C:6]([C:5]([Cl:3])=[O:15])=[CH:7][C:8](=[O:9])[NH:10]1 | O=C(O)c1cc(=O)[nH]c(=O)[nH]1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 55 | 0.75 | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.13 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 15.61 g (100 mmol) of orotic acid. Addition of the thionyl chloride is completed with heating to about 55° C. over the course... | O=C(Cl)c1cc(=O)[nH]c(=O)[nH]1 | null | null | null |
1,408,076 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [F:1][C:2]([F:47])([F:46])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:35]([N:36]2[CH2:41][CH2:40][CH:39]([C:42]([F:45])([F:44])[F:43])[CH2:38][CH2:37]2)=[CH:34][C:11]2[N:12]([CH3:33])[C:13]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH2:23][NH:24]C(OC(C)(C)C)=O)[C:17]=3[Cl:32])=[N:14][C:10]=2[CH:9]=1)=[O:7].Cl>C1COCC1... | Cn1c(Nc2c(Cl)ccc(CNC(=O)OC(C)(C)C)c2Cl)nc2cc(C(=O)NCCC(F)(F)F)c(N3CCC(C(F)(F)F)CC3)cc21 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 2 | A mixture of N-(3,3,3-trifluoropropyl)-2-{2,6-dichloro-3-[(tert.-butoxycarbonylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide (2.73 g, 3.8 mmol), 15 mL 6M aq HCl and 15 mL THF is stirred for 2 h, concentrated and the sub title compound is purified by chro... | Cn1c(Nc2c(Cl)ccc(CN)c2Cl)nc2cc(C(=O)NCCC(F)(F)F)c(N3CCC(C(F)(F)F)CC3)cc21 | null | null | null |
1,206,592 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [C:1]([N:8]([CH3:42])[CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:30][C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[C:16]([C:18]2[S:22][C:21]3[C:23]([F:28])=[CH:24][CH:25]=[C:26]([F:27])[C:20]=3[C:19]=2[Cl:29])=[O:17])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Br[C:45]1[CH:50]=[C... | COc1ccc(B(O)O)cc1CN(C(=O)c1sc2c(F)ccc(F)c2c1Cl)C1CCC(N(C)C(=O)OC(C)(C)C)CC1 | Brc1ccncc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Boronic acid 9 (5.70 g, 9.14 mmol) is coupled to 4-bromopyridine hydrochloride (2.13 g, 11.0 mmol) using Method A to give the title compound. | COc1ccc(-c2ccncc2)cc1CN(C(=O)c1sc2c(F)ccc(F)c2c1Cl)C1CCC(N(C)C(=O)OC(C)(C)C)CC1 | null | null | null |
1,531,848 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][C:7](=[O:13])[C:6]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:5]2[OH:21]>[OH-].[Na+].O.[Pd]>[OH:21][C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[CH:2][CH:3]=2)[S:8][C:7](=[O:13])[C:6]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15] | Cc1cc(Cl)cc2c(O)c(C(=O)NCC(=O)O)c(=O)sc12 | null | null | [Pd] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 18 | [(6-Chloro-4-hydroxy-8-methyl-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid (95 mg, 0.29 mmol) was dissolved in 1N sodium hydroxide (1.16 mL) and water (1.84 mL). 10% Palladium on carbon (9.5 mg) was added and the solution was vacuum purged and treated with hydrogen gas (1 atm). The reaction stirred overnight (1... | Cc1cccc2c(O)c(C(=O)NCC(=O)O)c(=O)sc12 | null | 88.2 | null |
1,268,342 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C([O:8][C:9]1[C:10]2[N:11]([CH:40]=[CH:41][N:42]=2)[C:12]([C:15]2[N:16]=[C:17]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:18]3[S:23][C:22]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([N:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]4)=[CH:21][C:19]=3[N:20]=2)=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH3:32][N:31]([CH3:... | CN(C)C1CCN(Cc2cc3nc(-c4ccc(OCc5ccccc5)c5nccn45)nc(N4CCOCC4)c3s2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 140 | null | A mixture of {1-[2-(8-benzyloxyimidazo[1,2-a]pyridin-5-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]piperidin-4-yl}dimethylamine (381 mg, 0.65 mmol) in TFA was heated at 140° C., for 10 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was wash... | CN(C)C1CCN(Cc2cc3nc(-c4ccc(O)c5nccn45)nc(N4CCOCC4)c3s2)CC1 | null | 10 | null |
200,675 | ord_dataset-31f00a039ca0424788e5e1970d25a8fd | null | 1989-01-01T00:12:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].O.[OH-].[Na+]>C(O)=O>[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10] | Cc1ccnc(N)n1 | O=Cc1ccc([N+](=O)[O-])cc1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=CO | null | null | null | null | null | null | null | null | null | null | null | The starting compound is prepared as follows. A solution of 2-amino-4-methylpyrimidine (21.8 g) and p-nitrobenzaldehyde (30.2 g) in formic acid (45 ml) is refluxed (24 hours). After cooling, the reaction mixture is poured into water (1 liter), and the aqueous mixture is neutralized with a 5N sodium hydroxide solution. ... | Nc1nccc(C=Cc2ccc([N+](=O)[O-])cc2)n1 | null | 57.5 | null |
102,808 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [BH4-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4]1.[OH2:12]>C(O)C>[OH:12][CH:5]([C:10]1[CH:9]=[CH:8][C:7]2[O:3][CH2:4][CH2:5][C:6]=2[CH:11]=1)[CH:6]([CH3:11])[CH3:7] | c1ccc2c(c1)CCO2 | O | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 1.5 | Sodium borohydride (1.11 g, 0.029 mol) was added portionwise to a stirred solution of 2,3-dihydrobenzofuran (5.46 g, 0.029 mol) in ethanol (20 cm3) over 0.5 hr. with cooling. The mixture was then stirred at 50°-70° C. for 1.5 hr., cooled, water was added and the mixture was extracted with dichloromethane. The extract w... | CC(C)C(O)c1ccc2c(c1)CCO2 | null | 95.2 | null |
1,008,180 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | Cl[C:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[CH:6][CH:5]=1)=[O:3].[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[O:30][CH:31]([CH3:33])[CH3:32])/[C:23](=[N:25]/O)/[NH2:24].Cl>N1C=CC=CC=1>[Cl:19][C:20]1[CH:21]=[C:22]([C:23]2[N:25]=[C:2]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10](... | CC(C)(C)OC(=O)COc1ccc(C(=O)Cl)cc1 | CC(C)Oc1ccc(/C(N)=N/O)cc1Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 200 | 0.42 | A 25 mL microwave reaction vial was charged with tert-butyl 2-(4-(chlorocarbonyl)phenoxy)acetate (0.815 g, 3.01 mmol) and pyridine (15 mL), (Z)-3-chloro-N′-hydroxy-4-isopropoxybenzimidamide (0.459 g, 2.007 mmol) was added. The vessel was capped and the reaction heated at 200° C. for 20 min under microwave irradiation (... | CC(C)Oc1ccc(-c2noc(-c3ccc(OCC(=O)O)cc3)n2)cc1Cl | null | 31.5 | null |
890,987 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | I[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[CH:3]=1.C([Mg]Cl)(C)C.CON(C)[C:29]([C:31]1[CH:35]=[C:34]([CH3:36])[O:33][N:32]=1)=[O:30]>C1COCC1>[CH3:36][C:34]1[O:33][N:32]=[C:31]([C:29]([C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]... | CON(C)C(=O)c1cc(C)on1 | Cc1cccc(Cn2cc(I)c(=O)c3ccccc32)n1 | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To the solution of 3-Iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one (300 mg, 0.82 mmol, 1.2 eq) in THF (2 ml), was added isopropylmagnesium chloride in THF (0.88 mL, 1.76 mmol, 2.1 eq) slowly at −40° C. The reaction mixture was warmed to room temperature and stirred for 60 min, followed by the addition of 5-Met... | Cc1cccc(Cn2cc(C(=O)c3cc(C)on3)c(=O)c3ccccc32)n1 | null | 10.2 | null |
1,046,188 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.C(O[CH:23](N(C)C)[N:24]([CH3:26])[CH3:25])(C)(C)C>>[CH3:23][N:24]([CH3:26])[CH:25]=[C:11]1[C:10](=[O:15])[CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=2)[CH2:14][CH2:13][CH... | CN(C)C(OC(C)(C)C)N(C)C | O=C1CCCCC1c1cccc(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(3-Trifluoromethyl-phenyl)-cyclohexanone (106 mg, 0.44 mmol) was reacted with tert.-butoxy-bis-(dimethylamino)-methane using in analogous manner the procedure described in example 45a), to give crude title compound (132 mg) as a red oil which was used directly in the next step. MS ISP (m/e): 298.0 [(M+H)+] | CN(C)C=C1CCCC(c2cccc(C(F)(F)F)c2)C1=O | null | null | null |
855,082 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15].[F:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:21]=3[F:20])[C:8]([F:12])=[C... | Nc1c(C(=O)NC2CC2)nnc2c(I)c(F)ccc12 | COc1cccc(B(O)O)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2-fluoro-3-methoxyphenylboronic acid (162 mg, 0.96 mmol) were reacted. After purification the title compound (100 mg, 56% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.04(d, J=4.8 Hz, 1H), 8.59 (m... | COc1cccc(-c2c(F)ccc3c(N)c(C(=O)NC4CC4)nnc23)c1F | null | 56.3 | null |
1,423,873 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Br[CH2:23][C:24]#[C:25][CH3:26].O>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][N:20]([CH2:23][C:24]#[C:25][CH3:26])[CH:21]=2)[C:12]([O:14... | CC#CCBr | CCOC(=O)C(Cc1ccc(N)nc1)c1c[nH]cn1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 1 | 11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (example 1g) in 0.5 ml of DMF at RT and stirred for 1 h. Then 31 mg (37 μl, 0.23 mmol) of 1-bromo-2-butine were added, and the mixture was stirred at RT for 1 h. 1 ml of... | CC#CCn1cnc(C(Cc2ccc(N)nc2)C(=O)OCC)c1 | null | 39 | null |
784,916 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:29]#[N:30])C1C=CC=CC=1>O1CCCC1.[C].[Pd]>[C:29]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[CH:21]=[C:22]2[C:... | N#Cc1cc2c(Oc3ccc4[nH]ccc4c3)ccnc2cc1OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 11 | After dissolving 7-benzyloxy-6-cyano-4-(1H-indol-5-yloxy)quinoline (3 g, 7.6642 mmol) in tetrahydrofuran (250 ml), 10% palladium carbon powder (500 mg, wet) was added and the mixture was stirred for 11 hours at room temperature under a hydrogen atmosphere. After further adding 10% palladium carbon powder (300 mg, wet) ... | N#Cc1cc2c(Oc3ccc4[nH]ccc4c3)ccnc2cc1O | null | 78.8 | null |
1,667,023 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [C:1]([O:4][CH:5]1[C:9]2=[N:10][CH:11]=[C:12]([NH2:29])[C:13]([N:14]3[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]3)=[C:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[F:30][C:31]1[CH:36]=[C:35]([CH2:37][O:38][CH3:39])[CH:34]=[C:33]([F:40])[C:32]=1[C:41]1[N:46]=[... | CC(=O)OC1CCc2c1ncc(N)c2N1C[C@H](C)C[C@H](NC(=O)OC(C)(C)C)C1 | COCc1cc(F)c(-c2nc(C(=O)O)ccc2F)c(F)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 2 | A mixture of 3-amino-4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (256 mg, 0.633 mmol), 6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxylic acid (188 mg, 0.633 mmol), HATU (481 mg, 1.26 mmol) in DMF (1 mL) and DIPEA (0.330 mL, 1.90... | COCc1cc(F)c(-c2nc(C(=O)Nc3cnc4c(c3N3C[C@H](C)C[C@H](NC(=O)OC(C)(C)C)C3)CCC4OC(C)=O)ccc2F)c(F)c1 | null | null | null |
1,204,813 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH:13]=[C:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:25][CH3:26])[CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][CH:14]([C:20](=[O:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:25][CH3:26])[CH:10]=1 | CCOC(=O)C(=Cc1ccc(OCc2ccccc2)cc1OC)C(C)=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 48 | A mixture of the product from step (i) (40 g) and 5% Pd—C (3 g) in EtOAc were hydrogenated at 3 Bar for 48 h. The mixture was filtered through celite and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 30% EtOAc/iso-hexane to afford the subtitle compound, 23.35 g. | CCOC(=O)C(Cc1ccc(O)cc1OC)C(C)=O | null | null | null |
751,407 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | Cl[C:2]1[N:7]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>CS(C)=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:6]3[CH:5]=[CH... | Fc1ccc(-c2nn3c(Cl)cccc3c2-c2ccncc2)cc1 | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of 7-chloro-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-α]pyridine (100 mg) and imidazole (5 eq.) in dimethylsulfoxide (2 mL) in sealed tube was heated at 120° C. overnight. The mixture was evaporated to dryness and purified by preparative thin layer chromatography to give 2-(4-fluorophenyl)-7-(1H-imidazol... | Fc1ccc(-c2nn3c(-n4ccnc4)cccc3c2-c2ccncc2)cc1 | null | null | null |
118,171 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [OH:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>>[C:26]([O:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:2... | COc1ccc(-c2nc(SCCO)sc2-c2ccc(OC)cc2)cc1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5.0 g of 2-(2-hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole are suspended in 50 ml of acetic anhydride and, while stirring, the suspension is heated to the boil and refluxed for 15 minutes. The product is concentrated to dryness by evaporation under reduced pressure, two 30 ml portions of xylene are added, with ... | COc1ccc(-c2nc(SCCOC(C)=O)sc2-c2ccc(OC)cc2)cc1 | null | null | null |
1,512,920 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]1([CH2:14][OH:15])[CH2:13][CH2:12]1.[OH-].[K+].Cl>CS(C)=O.O>[CH:11]1([CH2:14][O:15][C:2]2[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1 | OCC1CC1 | O=C(O)c1ccc(Cl)nc1 | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 25 | null | 6-Chloropyridine-3-carboxylic acid (1.00 g, 6.347 mmol), cyclopropylmethanol (0.759 mL, 9.520 mmol) and potassium hydroxide (1.424 g, 25.39 mmol) were dissolved in DMSO (25 mL) and heated at 100 C for 18 h. The reaction mixture was cooled to room temperature; water was added and acidified to pH 4-5 with 1M hydrochloric... | O=C(O)c1ccc(OCC2CC2)nc1 | null | 88 | null |
21,244 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | [C:1]1([CH:7]2[C:12](=[O:13])[NH:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18]Cl.CC(C)=O>C(N(CC)CC)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:18][N:8]1[CH2:9][CH2:10][NH:11][C:12](=[O:13])[CH:7]1[C:1]1[CH:2]=[CH:... | O=C1NCCNC1c1ccccc1 | ClCc1ccc(Cl)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 140 g. of 2-phenyl-3-keto piperazine are boiled under reflux with 163 g. of 3,4-dichloro benzylchloride in 1,600 cc. of acetone for 6 hours while 330 cc. of triethylamine are added. The hot reaction mixture is filtered to remove precipitated triethyl ammonium chloride and is concentrated by fractional distillation. The... | O=C1NCCN(Cc2ccc(Cl)c(Cl)c2)C1c1ccccc1 | null | null | null |
101,836 | ord_dataset-72d9f7ef86df410fac4765c9632d459b | null | 1983-01-01T00:01:00 | true | N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[F:7])(=[O:24])[CH3:23] | Oc1ccccc1Sc1ccccc1F | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Pyridine (1 ml) was added to a solution of 2-(2-fluorophenylthio)phenol (9.4 g) in acetic anhydride (10 ml), and the mixture was stirred at room temperature for 30 minutes. The excess of acetic anhydride was distilled off under reduced pressure, and the resultant oily residue was dissolved in diethyl ether. The ether s... | CC(=O)Oc1ccccc1Sc1ccccc1F | null | null | null |
1,148,077 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Br[C:2]1[C:3]([CH:16]=[C:17]2[CH:21]([OH:22])[CH2:20][CH2:19][S:18]2)=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:7]=1.C([O-])=O.[NH4+].C(N(CC)CC)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=... | COC(=O)C(C)c1cc(Br)c(C=C2SCCC2O)cc1OC | null | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 80 | 8 | Methyl 2-[5-bromo-4-(3-hydroxythiolan-2-ylidenemethyl)-2-methoxyphenyl]propionate (50 mg) obtained in Example 50 was dissolved in ethylene glycol dimethyl ether (2 ml), and then to the solution was added ammonium formate (25 mg), triethylamine (0.1 ml) and tetrakis(triphenylphosphine)palladium (50 mg). The mixture was ... | COC(=O)C(C)c1ccc(C=C2SCCC2O)cc1OC | null | 75.3 | null |
1,271,553 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([C:21]#[N:22])[CH:15]=3)[N:12]=[C:11]([C:23](O)=[O:24])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)C(C)C)(C)C.ClC1C=C(N2C(C3C=CC=C(OCCO)C=3)=CC(C([N:59]3[CH2:63][C:62](=[O:64])[NH:61][CH2:60]3)=O)=N2)C=CC=1>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4... | N#Cc1cc(-n2nc(C(=O)O)cc2-c2cc(F)cc(Cl)c2)ccc1F | O=C1CN(C(=O)c2cc(-c3cccc(OCCO)c3)n(-c3cccc(Cl)c3)n2)CN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | The preparation of the title compound takes place starting from the compound of Example 114A using 3.2 equivalents of N,N-diisopropylethylamine and with the addition of 0.1% formic acid in the preparative HPLC in analogy to the synthesis of the compound of Example 23. 44 mg (48% of theory) of the title compound are obt... | N#Cc1cc(-n2nc(C(=O)N3CNC(=O)C3)cc2-c2cc(F)cc(Cl)c2)ccc1F | null | null | null |
1,358,326 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | Cl.[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH2:14])[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CCN(CC)CC.[Cl:22][C:23]1[N:28]=[C:27](Cl)[N:26]=[C:25]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:24]=1>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH:14][C:27]2[N:28]=[C:23]([Cl:22])[N:24]=[C:25]([N... | CC(C)(C)OC(=O)N1CC(CN)C1 | Clc1nc(Cl)nc(N2CCOCC2)n1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of the 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester HCl salt (945 mg, 4.24 mmol) and NEt3 (856 mg, 8.48 mmol) in THF (10 mL) at 0° C. was added a suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4.24 mmol) at 0° C. The reaction mixture was stirred for another 1 hr at 0° C... | CC(C)(C)OC(=O)N1CC(CNc2nc(Cl)nc(N3CCOCC3)n2)C1 | null | 46 | null |
1,382,808 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH:1]1([O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:15]([C:20]2[N:24](COCC[Si](C)(C)C)[N:23]=[N:22][CH:21]=2)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:9]=[CH:8]3)[CH2:3][CH2:2]1.[F-].[Cs+].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:... | CC(C)C(O)(c1ccc2cc(OC3CC3)ccc2n1)c1cnnn1COCC[Si](C)(C)C | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [Cs+] | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of 1-(6-cyclopropoxyquinolin-2-yl)-2-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,3-triazol-5-yl)propan-1-ol (AR) (0.35 g, 0.77 mmol) in THF (5 mL) was added CsF (0.42 g, 3.08 mmol) followed by TBAF (1 mL, 0.77 mmol, 1M solution in THF) at RT and stirred under reflux for 12 h under inert ... | CC(C)C(O)(c1c[nH]nn1)c1ccc2cc(OC3CC3)ccc2n1 | null | 33.8 | null |
182,635 | ord_dataset-f25e1b7f8ef54305a5170f5395a768c7 | null | 1989-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[O:5][C:4](=O)[CH:3]=1.S([O-])([O-])(=O)=O.[OH:30][NH3+:31].O[NH3+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[OH:30][N:31]1[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([O... | Cc1cc(COc2ccc(Oc3ccc(Cl)cc3)cc2)oc(=O)c1 | [NH3+]O | null | O=C([O-])[O-] | O=S(=O)([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 171.4 g (0.5 mole) of 4-methyl-6-[4-(4-chlorophenoxy)phenoxymethyl]-2-pyrone in 50 ml of toluene were heated to 80° C. Then 59.9 g (0.36 mole) of hydroxylammonium sulfate and 38.3 g (0.36 mole) of sodium carbonate were added. 10 minutes later a further 59.9 g (0.36 mole) of hydroxylammonium sulfate and 38.3 g (0.36 mol... | Cc1cc(COc2ccc(Oc3ccc(Cl)cc3)cc2)n(O)c(=O)c1 | null | null | null |
136,500 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[N:20][C:6]1=2)=[O:4].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][NH:30]2)[CH2:24][CH2:23]1>>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH... | CN1CCN(C[C@@H]2CCCN2)CC1 | O=C1Nc2cccnc2N(C(=O)CCl)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared analogously to Example 31 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (S)-(+)-2-[(4-methyl-1-piperazinyl) methyl]pyrrolidine to give colorless crystals, mp. 182°-185° C. (D) (from ethyl acetate/methanol 99:1 v/v); [α]D20 =-11.2° (ethanol). | CN1CCN(C[C@@H]2CCCN2CC(=O)N2c3ccccc3C(=O)Nc3cccnc32)CC1 | null | null | null |
1,456,715 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [F:1][C:2]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])[C:12]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:13]=3[N:14]=2)[C:6]([F:27])=[CH:5][C:3]=1[NH2:4].[CH2:28]([N:30]=[C:31]=[O:32])[CH3:29]>>[F:1][C:2]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][O:23][CH2:22]... | C[C@H]1COCCN1c1nc(-c2cc(F)c(N)cc2F)nc2c1CCN(C)C2 | CCN=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method as example 85 using (S)-2,5-difluoro-4-(7-methyl-4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline and ethyl isocyanate as starting material. The solvent was removed in vacuo and purified twice by flash chromatography using 0-20% DCM/MeOH as eluent yielding the title compound (6.2 mg, ... | CCNC(=O)Nc1cc(F)c(-c2nc3c(c(N4CCOC[C@@H]4C)n2)CCN(C)C3)cc1F | null | 11 | null |
1,609,242 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N+:3]=1[O-:11].[ClH:12]>>[Cl:12][C:6]1[CH:5]=[CH:4][N+:3]([O-:11])=[C:2]([CH3:1])[CH:7]=1 | Cc1cc([N+](=O)[O-])cc[n+]1[O-] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-methyl-4-nitropyridine 1-oxide (5.0 g, 32 mmol, 1.0 eq) was dissolved in concentrated HCl (80 mL) and refluxed for 3 days. The reaction was cooled and the excess concentrated HCl was removed in vacuo. The viscous oil was neutralized with 10% K2CO3 and extracted with CH2Cl2 (5×). The combined organics were dried (MgSO... | Cc1cc(Cl)cc[n+]1[O-] | null | 75 | null |
916,635 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [OH:1][C:2]1[CH:6]([CH:7]([CH3:9])[CH3:8])[NH:5][C:4](=[O:10])[C:3]=1[CH:11]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:12]1[NH:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23]C(=O)C)=[CH:18][CH:17]=[CH:16][CH:15]=2.[Li+].[OH-]>CO>[OH:1][C:2]1[CH:6]([CH:7]([CH3:8])[CH3:9])[NH:5][C:4](=[O:10])[C:3]=1[CH:11]([C:12]... | CC(=O)OCCc1c(C(C2=C(O)C(C(C)C)NC2=O)c2ccccc2)[nH]c2ccccc12 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of acetic acid 2-{2-[(4-hydroxy-5-isopropyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-phenyl-methyl]-1H-indol-3-yl}-ethyl ester (40 mg) and LiOH (8.5 mg ) in MeOH (0.5 ml) was stirred at 22° C. for 30 min and evaporated. The residue was partitioned between 0.1 N aqueous HCl and AcOEt and the organic layer was dried ... | CC(C)C1NC(=O)C(C(c2ccccc2)c2[nH]c3ccccc3c2CCO)=C1O | null | null | null |
1,384,767 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [CH:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([OH:13])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[NH2:27]>>[CH:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=2)[C:11]([NH:27][C:22]2[CH:23]=[N:... | O=C(O)c1cnc(OCC(F)(F)F)c(C2CCCC2)c1 | Nc1cnccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared following the same procedure as described in Example 11 using 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (Example 9c) (50 mg, 0.17 mmol) and 2-pyrazinamine (CAN 5049-61-6, 20 mg, 0.21 mmol) as starting materials; off white solid (15 mg, 23.7%). MS (ESI): 365.2 (M+H)+. | O=C(Nc1cnccn1)c1cnc(OCC(F)(F)F)c(C2CCCC2)c1 | null | null | null |
1,232,124 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH:22]([OH:24])[CH3:23])[N:15](C(OC(C)(C)C)=O)[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:32]>C(Cl)Cl.O1CCOCC1>[ClH:32].[ClH:32].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:... | CC(O)c1cccc2c1C1(CCN(Cc3ccccc3)CC1)CN2C(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | A solution of tert-butyl 1′-benzyl-4-(1-hydroxyethyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (0.045 g, 0.11 mmol) in DCM (2 mL) was treated with 4N HCl in dioxane (0.5 mL). The reaction was stirred at room temperature for 4 hours and concentrated under reduced pressure to yield 1-(1′-benzylspiro[indoline-3,4′-pip... | CC(O)c1cccc2c1C1(CCN(Cc3ccccc3)CC1)CN2 | null | 100 | null |
489,930 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [C:1]([O:5][P:6]([C:13]([F:43])([F:42])[C:14]1[CH:41]=[CH:40][C:17]([CH2:18][CH:19]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[... | CC(C)(C)OP(=O)(OC(C)(C)C)C(F)(F)c1ccc(CC(C(=O)OCc2ccccc2)C(=O)OCc2ccccc2)cc1 | FC(F)(F)c1ccc(CBr)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.25 | To a solution of the product from Example 18, Step 1 (94 mg, 0.15 mmol) in DMF (2 mL) at 0° C. was added NaH (5.5 mg, 80% in oil). After 15 min., 4-(trifluoromethyl)benzyl bromide (44 mg, 0.18 mmol) was added. After 2 h at 0° C., the mixture was given a standard aqueous/Et2O work-up, and the residue was purified by fla... | CC(C)(C)OP(=O)(OC(C)(C)C)C(F)(F)c1ccc(CC(Cc2ccc(C(F)(F)F)cc2)(C(=O)OCc2ccccc2)C(=O)OCc2ccccc2)cc1 | null | 45.6 | null |
483,722 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18][CH3:19])=[N:14][CH:15]=2)[N:10]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][O:27]C3CCCCO3)=[CH:22][CH:21]=2)[C:9]1=[O:34]>Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([S:18][C... | CSc1ncc2c(n1)N(c1ccc(COC3CCCCO3)cc1)C(=O)N(c1ccccc1Br)C2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.945 mg (1.75 mmol) of 3-(2-bromophenyl)-3,4-dihydro-1-[4-(tetrahydropyran-2-yloxymethyl)phenyl]-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one in 10 ml of saturated hydrogen chloride in ethyl acetate was stirred at room temperature for 2 hours. The reaction was diluted with ethyl acetate (10 ml) then w... | CSc1ncc2c(n1)N(c1ccc(CO)cc1)C(=O)N(c1ccccc1Br)C2 | null | 85 | null |
499,401 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:6][O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[CH3:24][O:25]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=1)([CH2:1... | CC(=O)NC(CCc1ccccc1)(COC(C)=O)COC(C)=O | COC(Cl)Cl | null | Cl[Ti](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 2-acetamido-1, 3-diacetoxy-2-(2-phenylethyl)propane (10 g) in anhydrous dichloromethane (150 ml) were added titanium tetrachloride (15.4 ml) and dichloromethyl methyl ether (5.63 ml) under a nitrogen atmosphere at −15° C. The mixture was stirred at room temperature for 2 hours, poured into ice water an... | CC(=O)NC(CCc1ccc(C=O)cc1)(COC(C)=O)COC(C)=O | null | null | null |
195,992 | ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9 | null | 1989-01-01T00:09:00 | true | [OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([OH:21])[C:10]=3[C:11]=2[CH3:12])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:2]([O:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13... | CCCc1cc(Cl)c2oc(Cc3ccc(O)cc3)c(C)c2c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-(p-hydroxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (1 gm; 3 mmoles) in pyridine (15 mL) and acetic anhydride (3 mL) was stirred at 50° C. for 15 minutes. The volatiles were removed in vacuo leaving a residue that crystallised on cooling. It was slurried with hexane, filtered, washed with h... | CCCc1cc(Cl)c2oc(Cc3ccc(OC(C)=O)cc3)c(C)c2c1OC(C)=O | null | 176.8 | null |
438,082 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [C:1]([OH:5])#[C:2][CH2:3][CH3:4].I[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(#N)C.[Cu]I>[OH:5][CH2:1][CH2:2][C:3]#[C:4][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1 | CCC#CO | COC(=O)Cc1ccc(I)cc1 | null | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 3 | To a solution of butyn-1-ol (0.76 g, 0.11 mol) and methyl 4-iodophenylacetate (1.5 g, 0.0054 mol) in acetonitrile (10 mL) at 0° C., triethylamine (1.5 mL, 0.01 mol) was added, followed by the addition of bistriphenylphosphine palladium chloride (0.25 g, 0.36 mmol) and CuI (0.025 g). The reaction mixture was stirred at ... | COC(=O)Cc1ccc(C#CCCO)cc1 | null | 84.9 | null |
1,384,737 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [C:1]1([C:7]2[C:8]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:9][CH:10]=[C:11]([CH:15]=2)[C:12]([OH:14])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[F:22][C:23]([F:32])([F:31])[C:24]1[N:28]=[C:27]([CH2:29][NH2:30])[O:26][N:25]=1>>[C:1]1([C:7]2[C:8]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:9][CH:10]=[C:11]([CH:15]... | NCc1nc(C(F)(F)F)no1 | O=C(O)c1cnc(OCC(F)(F)F)c(C2=CCCCC2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to Example 1b using 5-cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid (Example 2b) and 3-(trifluoromethyl)-1,2,4-oxadiazole-5-methanamine (944905-93-5) as starting materials; MS (ESI) 451.2 (M+H)+. | O=C(NCc1nc(C(F)(F)F)no1)c1cnc(OCC(F)(F)F)c(C2=CCCCC2)c1 | null | null | null |
1,133,081 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | Cl.[O:2]=[C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]21[CH2:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([NH:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([C:27](O)=[O:28])[CH:22]=3)[CH:17]=1)[CH2:12]2.[F:30][C:31]1[CH:32]=[C:33]([C@@H:38]2[CH2:43][CH2:42][C:41]([CH3:45])([CH3:44])[CH2:40][NH:39]2)[CH:34]=[C:35]([F:37]... | O=C(O)c1cc(Nc2ccc3c(c2)CC2(C3)C(=O)Nc3ncccc32)ncn1 | CC1(C)CC[C@@H](c2cc(F)cc(F)c2)NC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | 64 mg (0.17 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 70 mg (0.16 mmol) (S)-2-(3,5-difluorophenyl)-5,5-dimethylpiperidine, 40 μL (0.23 mmol) DIPEA and 65 mg (0.17 mmol) HATU in 0.80 mL DMF were stirred overnight at RT. The purifica... | CC1(C)CC[C@@H](c2cc(F)cc(F)c2)N(C(=O)c2cc(Nc3ccc4c(c3)CC3(C4)C(=O)Nc4ncccc43)ncn2)C1 | null | null | null |
1,206,491 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)=O.[NH:18]([C:20]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:24](=[O:35])[N:23]([CH3:36])[C:22](=[O:37])[CH:21]=1)[NH2:19]>CCOC(C)=O>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[... | COc1ccc(Cn2c(NN)cc(=O)n(C)c2=O)cc1 | O=Cc1ccc(-c2ccccc2)cc1 | null | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 2 | A solution of 4-phenylbenzaldehyde (395 mg, 2.17 mmol) in EtOAc is slowly added into a dry ice cooled slurry of 6-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (200 mg, 0.724 mmol) in EtOAc. After the addition, the reaction mixture is stirred at room temperature for 2 hours. The solvent is evaporat... | COc1ccc(Cn2c(NN=Cc3ccc(-c4ccccc4)cc3)cc(=O)n(C)c2=O)cc1 | null | 80.3 | null |
1,635,513 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Cl[C:2]1[C:3]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([O:23]C)=[O:22])[CH:16]=2)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:25][C:26]([F:36])([F:35])[O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN1C(=O)CCC1.O>[F:25][C:26]([F:35])([F:3... | Oc1ccc(OC(F)(F)F)cc1 | COC(=O)c1cc(NC(=O)c2nc3ccccc3nc2Cl)ccn1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 80 | 0.17 | A solution of methyl 4-[(3-chloroquinoxaline-2-carbonyl)amino]pyridine-2-carboxylate (2.6 g, 7.59 mmol), 4-(trifluoromethoxy)phenol (982.5 μL, 7.59 mmol) and K2CO3 (3.14 g, 22.76 mmol) in NMP (52.00 mL) was stirred at 70° C. for two hours and at room temperature for 12 hours. 120 ml of water were added and the reaction... | O=C(O)c1cc(NC(=O)c2nc3ccccc3nc2Oc2ccc(OC(F)(F)F)cc2)ccn1 | null | 61.6 | null |
217,879 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[OH-].[OH-].[Na+].Cl.[N+:18]([CH3:21])([O-:20])=[O:19]>O.CO>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[CH:21][N+:18]([O-:20])=[O:19] | COc1cccc(C=O)c1[N+](=O)[O-] | C[N+](=O)[O-] | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 5 | 1 | Compound 2 was prepared according to the procedure of A. Kalir et al. [Isr. J. Chem. 5: 129-136 (1967)]. To a 100-mL round bottom flask, 6.674 g of powdered 3-methoxy-2-nitrobenzaldehyde (98%, Aldrich) (36.87 mmol), 2.1 mL of nitromethane (39 mmol), and 15.5 mL of methanol were added. This suspension was cooled to appr... | COc1cccc(C=C[N+](=O)[O-])c1[N+](=O)[O-] | null | 71 | null |
164,037 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=3)[CH:11]=[C:12]([C:19](=[O:21])[CH:20]=2)[C:13]([O:15]COC)=[O:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)C>C(O)C>[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]... | COCOC(=O)c1cn(-c2ccc(OCOC)cc2)c(-c2ccc(N(C)C)cc2)cc1=O | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCO | null | null | null | null | null | null | null | null | null | null | null | In 1 ml of ethanol was dissolved 0.08 g of methoxymethyl 6-(4-dimethylaminophenyl)-1-(4-methoxymethyloxyphenyl)-4-oxo-1,4-dihydronicotinate at room temperature, and 1 ml of a 10% by weight aqueous sodium carbonate solution was added to the resulting solution. The resulting mixture was subjected to reaction at the same ... | COCOc1ccc(-n2cc(C(=O)O)c(=O)cc2-c2ccc(N(C)C)cc2)cc1 | null | 83.4 | null |
509,627 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:35]=[CH:34][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([OH:33])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:38](Br)[CH2:39][CH2:40][CH2:41][CH3:42]>... | CCCCCBr | CC(C)(C)OC(=O)N1CCCC(CCCn2c(COc3ccc(Cl)cc3)nc3c(O)cccc32)C1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of (RS) 2-(4-chlorophenoxymethyl)-4-hydroxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]benzimidazole (75 mg, 0.15 mmol, 1.0 eq) in dry N,N-dimethylformamide (1.0 ml) was treated with sodium hydride (60% in oil, 7.5 mg, 0.18 mmol, 1.20 eq). The resulting mixture was stirred at room temperature for thirty... | CC(C)(C)OC(=O)N1CCCC(CCCCCOc2cccc3c2nc(COc2ccc(Cl)cc2)n3CCCC2CCCN(C(=O)OC(C)(C)C)C2)C1 | null | null | null |
1,433,936 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([NH2:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22].C(N(CC)C(C)C)(C)C>C(Cl)Cl.Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([Br:14])=[CH:12][C:11]([NH:15][C:21](=[O:22])[C:20... | CC(C)(C)OC(=O)Nc1ncc(N)cc1Br | O=C(Cl)c1cccc(F)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | (5-Amino-3-bromo-pyridin-2-yl)-carbamic acid tert-butyl ester (50 mg, 0.17 mmol), 3-fluoro-benzoyl chloride (28 mg, 0.17 mmol), and N,N-diisopropylethylamine (0.03 mL, 0.19 mmol) were dissolved in CH2Cl2 (2 mL), and stirred or 1 h at 0° C. The reaction solution was diluted with 1 M HCl/CH2Cl2, and filtered through an E... | CC(C)(C)OC(=O)Nc1ncc(NC(=O)c2cccc(F)c2)cc1Br | null | 67.4 | null |
1,689,551 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [C:1]1([C:7]2[C:12](B(O)O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[C:21]([C:22]2[CH:23]=[C:24](C3C(C)=CC=C4C=3C=CC=N4)[C:25]3[O:29][C:28](=[O:30])[NH:27][C:26]=3[CH:31]=2)=[C:20]([CH3:43])[O:19][N:18]=1>>[CH3:16][C:17]1[C:21]([C:22]2[CH:23]=[C:24]([C:12]3[C:7]([C:1]4[CH:6]=[CH:5]... | Cc1ccc2ncccc2c1-c1cc(-c2c(C)noc2C)cc2[nH]c(=O)oc12 | OB(O)c1cccnc1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized using 2-phenylpyridin-3-ylboronic acid in a similar fashion with 5-(3,5-dimethylisoxazol-4-yl)-7-(6-methylquinolin-5-yl)benzo[d]oxazol-2(3H)-one (Example 11). | Cc1noc(C)c1-c1cc(-c2cccnc2-c2ccccc2)c2oc(=O)[nH]c2c1 | null | null | null |
859,805 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [OH:1][C:2]1[C:3]([C:19](OC)=[O:20])=[N:4][N:5]2[CH:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][N:8]([CH3:17])[C:7](=[O:18])[C:6]=12.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>CO>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:19]([C:3]2[C:2]([OH:1])=[C:6]3[C:7](=[O:18])[N:... | NCc1ccc(F)cc1 | COC(=O)c1nn2c(c1O)C(=O)N(C)CC2c1cccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Methyl 3-hydroxy-5-methyl-4-oxo-7-pyridin-3-yl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (40 mg, 0.13 mmol) and 4-fluorobenzylamine (130 mg, 1.06 mmol) were combined in MeOH (0.5 mL) and the mixture was heated to reflux, allowing the solvent to slowly evaporate over 18 hours. The residue was purified by p... | CN1CC(c2cccnc2)n2nc(C(=O)NCc3ccc(F)cc3)c(O)c2C1=O | null | null | null |
1,054,225 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:30])[N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[C:13]([C:15]2[NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[N:23]=2)[CH:14]=1)#[N:2].[CH3:31]I>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:30])[N:11]([C:24]2[CH... | N#Cc1ccccc1-c1cc(-c2nc3cnccc3[nH]2)cn(-c2ccccc2)c1=O | CI | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 3 mg of 3-(2-cyanophenyl)-5-(1H-imidazo[4,5-c]pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 3 ml of acetone. To the mixture was added 2 ml of methyl iodide, followed by stirring at room temperature overnight. The mixture was evaporated, and the residue was diluted with 1 ml of water. To the mixture w... | Cn1cccc2nc(-c3cc(-c4ccccc4C#N)c(=O)n(-c4ccccc4)c3)nc1-2 | null | null | null |
1,072,548 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1 | O=P(Cl)(Cl)Cl | Oc1ccnc2ccncc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1,6-naphthyridin-4-ol (0.530 g, 3.63 mmol) was dissolved in phosphorus oxychloride (4.06 ml, 43.5 mmol) and heated at reflux for 14 h. Excess POCl3 was removed under reduced pressure and the mixture was azeotroped with toluene. The resultant gum was treated with sat. NaHCO3 until no gas was generated. The mixture was e... | Clc1ccnc2ccncc12 | null | null | null |
361,624 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [Br:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.O.O.[C:13](O)(=[O:17])[C:14](O)=[O:15]>Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Br:8])[NH:9][C:14](=[O:15])[C:13](=[O:17])[NH:10]2 | Nc1cc(Br)c(Br)cc1N | O=C(O)C(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 125 | null | A mixture of 4,5-dibromo-1,2-phenylenediamine (1.862 g, 7.0 mmol) and oxalic acid dihydrate (1.06 g, 8.4 mmol) in 2N HCl (100 mL) was heated at 125° C. for 2 h then allowed to cool to 25° C. The solid was collected by vacuum filtration, washed with water and dried at 40° C. under 1 mmHg for 10 h affording 2.053 g (92%)... | O=c1[nH]c2cc(Br)c(Br)cc2[nH]c1=O | null | 91.7 | null |
469,752 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [OH:1][C@@H:2]([C@H:4]1[C:38](=[O:39])[N:6]2[C:7]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)=[O:26])=[C:8](P(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:9]([CH3:10])[C@@H:5]12)[CH3:3].[OH:40][CH:41]([CH2:72][NH:73][C:74]([O:76][CH2:77][C:78]1[CH:83]=[CH:82][C:81]([N+:84]([O-:86])=... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(P(=O)(c3ccccc3)c3ccccc3)[C@H](C)[C@@H]12 | O=C(CC(O)CNC(=O)OCc1ccc([N+](=O)[O-])cc1)N[C@H]1CCN(C(=O)[C@@H]2C[C@H](S)CN2C(=O)OCc2ccc([N+](=O)[O-])cc2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-diphenylphosphoryl-1-carbapen-2-em-3-carboxylate (1.78 g) and (2S,4S)-2-[(3S)-3-[3-hydroxy-4-(4-nitrobenzyloxycarbonyl)aminobutanoylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.0 g), reaction and purification we... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(S[C@H]3C[C@@H](C(=O)N4CC[C@H](NC(=O)CC(O)CNC(=O)OCc5ccc([N+](=O)[O-])cc5)C4)N(C(=O)OCc4ccc([N+](=O)[O-])cc4)C3)[C@H](C)[C@H]12 | null | 83.4 | null |
29,273 | ord_dataset-dc78376bd0a946d1a5a41eec30282b7d | null | 1977-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl[CH2:11][CH:12]=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][CH2:11][CH:12]=[O:13] | Cc1cccc(C)c1N | O=CCCl | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 150 | null | 2,6-Dimethylaniline (60 grams), the dimethyl acetal of 2-chloroacetaldehyde (25 grams) and sodium carbonate (21.2 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at 150° C. for a period of about 30 hours. After this t... | Cc1cccc(C)c1NCC=O | null | null | null |
1,469,491 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C(N(C(C)C)CC)(C)C.[NH:10]([CH2:14][CH2:15][OH:16])[CH2:11][CH2:12][OH:13].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:29]=[C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:32]([F:42])[CH:31]=3)[O:27][N:26]=2)=[CH:21][CH:20]=1>CN(C)C=O>[F:42][C:32]1[CH:31]=[C:30]([C:28]2[O:27][N... | Fc1cc(-c2nc(-c3ccc(CCl)cc3)no2)ccc1-c1ccccc1 | OCCNCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 90 | null | Diisopropylethylamine (23.5 mL, 0.136 mol) and diethanolamine (14.2 g, 0.135 mol) are added to a stirred solution of 3-(4-chloromethylphenyl)-5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole (33 g, 0.090 mol) in N,N-dimethyl-formamide (200 mL). The reaction mixture is heated at 90° C. for 2.5 hrs, the solvent is removed unde... | OCCN(CCO)Cc1ccc(-c2noc(-c3ccc(-c4ccccc4)c(F)c3)n2)cc1 | null | null | null |
241,727 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[C:4](=[O:17])[NH:5][C:6](=NC2C=CC=CC=2)[C:7]=1[O:8][CH3:9].Cl.[OH2:19]>>[CH3:1][O:2][C:3]1[C:4](=[O:17])[NH:5][C:6](=[O:19])[C:7]=1[O:8][CH3:9] | COC1=C(OC)C(=Nc2ccccc2)NC1=O | O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 500 g of 2,5-dihydro-3,4-dimethoxy-5-phenyliminopyrrol-2-one were stirred with 500 ml of concentrated hydrochloric acid in 2 l of water for 2 days at room temperature. Thereafter, the mixture was cooled and filtered under suction. 325 g of dimethoxymaleimide of melting point 126°-127° C. were obtained. | COC1=C(OC)C(=O)NC1=O | null | null | null |
1,767,410 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][C@@H:19]1[CH2:24][NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1>>[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:7]([C:... | C[C@@H]1CCCN[C@@H]1CNc1ccc(C(F)(F)F)cn1 | Cc1ccc(-c2cncn2C)c(C(=O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following the same general protocol as described in Example A1, using 5-methyl-2-(1-methyl-1H-imidazol-5-yl)benzoic acid and N-(((2S,3R)-3-methylpiperidin-2-yl)methyl)-5-(trifluoromethyl)pyridin-2-amine. ESI-MS (m/z): 472 [M+1]+. | Cc1ccc(-c2cncn2C)c(C(=O)N2CCC[C@@H](C)[C@H]2CNc2ccc(C(F)(F)F)cn2)c1 | null | null | null |
1,750,628 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | C(OC([NH:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:21]>>[ClH:21].[NH2:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10] | COC(=O)c1ccc([C@H](C)NC(=O)OC(C)(C)C)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 1 | To methyl (S)-4-(1-tert-butoxycarbonylaminoethyl)benzoate (1.00 g, 3.58 mmol), add hydrogen chloride (4 M in dioxane, 5 mL, 20 mmol) and stir the resulting mixture at room temperature for one hour. Concentrate the mixture under reduced pressure to furnish the title compound as a white solid (750 mg, 97% yield). 1H NMR ... | COC(=O)c1ccc([C@H](C)N)cc1 | null | 97.1 | null |
1,576,796 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[OH:16])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][C:4]=1[O:16][CH2:24][CH:25]=[C:26]([CH... | N#Cc1ccc(Nc2ccccn2)cc1O | CC(C)=CCBr | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Following the general procedure for O-alkylation of 2-R-5-(heteroaryl-2-ylamino)phenol, 2-cyano-5-(pyridin-2-ylamino)phenol (2 mg, 0.01 mmol) and Cs2CO3 (3 mg, 0.01 mmol) in acetone (1.5 mL) was treated with 4-bromo-2-methyl-2-butene (1.1 μL, 0.01 mmol) at room temperature. The title compound was obtained after purific... | CC(C)=CCOc1cc(Nc2ccccn2)ccc1C#N | null | 38 | null |
1,632,504 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][N:9]=1.[CH:16]1([CH2:19][O:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2B(O)O)[CH2:18][CH2:17]1>>[CH:16]1([CH2:19][O:20][C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[C:2]2[N:6]([CH3:7])[CH:5]=[N:4][C:3]=2[C:8]2[... | Cn1cnc(-c2cc(C#N)ccn2)c1Br | OB(O)c1ccc(F)cc1OCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(5-bromo-1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (PREPARATION 2) and 2-(cyclopropylmethoxy)-4-fluorophenylboronic acid according to the procedure for the preparation of Example 3, part A. [M+H] Calc'd for C20H17FN4O, 349. Found, 349. | Cn1cnc(-c2cc(C#N)ccn2)c1-c1ccc(F)cc1OCC1CC1 | null | null | null |
505,301 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18](=[O:22])[C:19](Cl)=[O:20])=[C:10]1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1>O1CCCC1>[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18](=[O:22])[C:... | CC1CCNCC1 | Cn1c(COc2ccc(Cl)cc2)c(C(=O)C(=O)Cl)c2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 8 | Under a nitrogen atmosphere, 4-methylpiperidine (0.490 ml, 0.411 g, 4.14 mmol) was dissolved in 3.0 ml of dry tetrahydrofuran in a round bottom flask over an ice bath. To this reaction mixture was added 1-methyl-2-(4-chlorophenoxymethyl)-3-[2-chloro-1,2-ethanedionyl]-1H-indole (0.500 g, 1.39 mmol) and the resulting mix... | CC1CCN(C(=O)C(=O)c2c(COc3ccc(Cl)cc3)n(C)c3ccccc23)CC1 | null | null | null |
459,262 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH2:8][N:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[O:11][C:10]2=[O:24])[CH:7]=1.[C:26](Cl)([Cl:28])=[O:27]>C1(C)C=CC=CC=1>[Cl:28][C:26]([O:25][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[CH2:8][N:9]1[N:13]=[C:12]([C:14]... | O=C(Cl)Cl | O=c1oc(-c2ccc(C(F)(F)F)cc2)nn1Cc1cc(Cl)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 120 | null | A stirred suspension of 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one (1 g, 2.69 mmol) and BnPh3PCI (25 mg) in 1.9 molar toluene solution of phosgene (15 mL) was heated at 120° C. overnight in a sealed tube. After removal of excess phosgene, the toluene solution was rotary... | O=C(Cl)Oc1ccc(Cl)cc1Cn1nc(-c2ccc(C(F)(F)F)cc2)oc1=O | null | null | null |
236,492 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=[O:11])[C:7]([NH:13][C:14]([C:16]([O:18]CC)=O)=[O:15])=[CH:6][C:3]=1[C:4]#[N:5].CN(C)C=O.N>O1CCCC1.[Pd]>[Cl:1][C:2]1[CH:9]=[C:8]2[C:7]([NH:13][C:14](=[O:15])[C:16](=[O:18])[N:10]2[OH:11])=[CH:6][C:3]=1[C:4]#[N:5] | CCOC(=O)C(=O)Nc1cc(C#N)c(Cl)cc1[N+](=O)[O-] | null | null | [Pd] | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 0.6 g (2.0 mmol) 2-chloro-5-ethoxalylamino-4-nitrobenzonitril in 50 ml tetrahydrofuran was added 15 ml dimethylformamide and 0.7 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 0.1 g Pd-C as a catalyst. The catalyst was filtered off, and the filter cake was washed with te... | N#Cc1cc2[nH]c(=O)c(=O)n(O)c2cc1Cl | null | 52.6 | null |
1,387,940 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([O:17][CH3:18])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20]>C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=C... | COC1CCC2(CC1)Cc1ccc(Br)cc1C2=O | N#Cc1cccc(B(O)O)c1 | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 100 | 0.1 | To a solution of 6′-bromo-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (40 mg, 0.130 mmol) and 3-cyanophenylboronic acid (30.5 mg, 0.208 mmol) in Cs2CO3 (2 M, 0.247 mL) and 1,4-dioxane (1.2 mL) under N2 was added Pd(PPh3)2Cl2 (7.5 mg). The mixture was stirred at 100° C. for 6 minutes. After cooled to room tempera... | COC1CCC2(CC1)Cc1ccc(-c3cccc(C#N)c3)cc1C2=O | null | 46.4 | null |
461,992 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11]3[CH2:12][CH2:13][N:14]4[C:19]([C:10]=3[NH:9][C:6]2=[CH:7][CH:8]=1)=[CH:18][CH2:17][CH2:16][C:15]4=[O:20]>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11]3[CH:12]=[CH:13][N:14]4[C:19]([C:10]=3[NH:9][C:6]2=[CH:7][CH:8]=1)=[CH:18][CH:17]=[CH:16][C:15]4=[O:20] | COc1ccc2[nH]c3c(c2c1)CCN1C(=O)CCC=C31 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | Activated manganese dioxide (400 mg) is added to a solution of 9-methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one (150 mg) in THF (5 ml). After refluxing for 2 h 30, the mixture is cooled and activated manganese dioxide (400 mg) is again added. The medium is refluxed for 24 h. After filtration ard washing of... | COc1ccc2[nH]c3c(ccn4c(=O)cccc34)c2c1 | null | null | null |
1,479,101 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [C:1]([N:5]1[CH2:22][CH:21]([CH2:23][O:24][CH3:25])[O:20][C:7]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1>ClCCl>[C:1]([N:5]1[CH2:22][CH:21]([CH2:23][O:24][CH3:25])[O:20][C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2] | COCC1CN(C(C)(C)C)CC2(CCN(C(=O)OC(C)(C)C)CC2)O1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | null | 1.5 | Tert-butyl 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (732 mg, 2.05 mmol) was dissolved in dichloromethane (10 mL) and treated dropwise with a solution of HCl in dioxane (12.8 mL of 4 M, 51.3 mmol). The reaction was stirred for 1.5 h and then diluted with dichloromethane. The organ... | COCC1CN(C(C)(C)C)CC2(CCNCC2)O1 | null | 100 | null |
1,348,556 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([N:3]1[CH2:9][CH2:8][C:7]2[C:10]([NH2:16])=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:6]=2[CH2:5][CH2:4]1)[CH3:2].Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([NH:29][CH3:30])=[O:28])[C:21]([Cl:35])=[CH:20][N:19]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[Na]>O.CC(O)C>[Cl:35][C:21]1... | CCN1CCc2c(N)ccc(OC)c2CC1 | CNC(=O)c1ccccc1Nc1nc(Cl)ncc1Cl | null | CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2 | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | 120 | null | 3-Ethyl-9-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ylamine (50.01 mg, 0.2270 mmol), 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (67.4 mg, 0.227 mmol) and 10-camphorsulfonic acid (79.1 mg, 0.340 mmol) were charged to 2 ml IPA in a microwave tube. The reaction was heated to at 120° C. for 40 minutes. Po... | CCN1CCc2c(Nc3ncc(Cl)c(Nc4ccccc4C(=O)NC)n3)ccc(OC)c2CC1 | null | null | null |
108,114 | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | null | 1983-01-01T00:08:00 | true | C([S:9][CH2:10][CH:11]([CH3:26])[C:12]([N:14]1[CH2:22][CH:21]2[N:17]([CH2:18][CH2:19][CH2:20]2)[CH2:16][CH:15]1[C:23]([OH:25])=[O:24])=[O:13])(=O)C1C=CC=CC=1>CO>[SH:9][CH2:10][CH:11]([CH3:26])[C:12]([N:14]1[CH2:22][CH:21]2[N:17]([CH2:18][CH2:19][CH2:20]2)[CH2:16][CH:15]1[C:23]([OH:25])=[O:24])=[O:13] | CC(CSC(=O)c1ccccc1)C(=O)N1CC2CCCN2CC1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 6 | By allowing a solution of (-)4-(3-benzoylthio-2-methylpropionyl)-1,4-diazabicyclo[4.3.0]nonane-3-carboxylic acid in ammoniacal methanol to stand at 25° C. for 4-8 hours the title compound is obtained. | CC(CS)C(=O)N1CC2CCCN2CC1C(=O)O | null | null | null |
555,376 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | [C:1]([BH3-])#[N:2].[Na+].C([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([OH:16])[CH:8]=1)=O.C(=O)([O-])O.[Na+]>O>[C:11]([C:10]1[CH:14]=[CH:15][C:7]([CH2:1][NH2:2])=[CH:8][C:9]=1[OH:16])([OH:13])=[O:12] | O=Cc1ccc(C(=O)O)c(O)c1 | [BH3-]C#N | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 4 | Sodium cyanoborohydride (32 mg; 0.5 mmol) was added to a mixture of PAMAM 4.0 (EDA) (69 mg; 0.01 mmol), 4-formyl-2-hydroxybenzoic acid (83 mg; 0.5 mmol), and sodium hydrogen carbonate (42 mg; 0.5 mmol) in water (4 ml). The inhomogeneous orange mixture was stirred for four hours at room temperature, during which time it... | NCc1ccc(C(=O)O)c(O)c1 | null | null | null |
1,314,535 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [C:1](=[O:5])([O:3][CH3:4])[NH2:2].O=[C:7]([CH2:11][CH2:12][PH:13]([CH2:15][OH:16])=[O:14])[C:8]([OH:10])=[O:9].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:4][O:3][C:1]([NH:2]/[C:7](=[CH:11]\[CH2:12][PH:13]([CH2:15][OH:16])=[O:14])/[C:8]([OH:10])=[O:9])=[O:5] | COC(N)=O | O=C(O)C(=O)CC[PH](=O)CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 1 | 5.835 g of methyl carbamate and 10.000 g of 2-oxo-4-(hydroxymethylphosphinyl)-butanoic acid were added to 17 mL of acetic acid to be suspended. After being dissolved by heating, 68 mL of toluene was added thereto and then the solution was refluxed with vigorous stirring. The internal temperature of the reaction solutio... | COC(=O)N/C(=C\C[PH](=O)CO)C(=O)O | null | 75.4 | null |
969,823 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [Br:1]N1C(=O)CCC1=O.[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]([O:28]CC)=[CH2:27])[C:12]=1[CH3:31])#[N:10]>O1CCCC1.O>[Br:1][CH2:28][C:26]([C:13]1[C:12]([CH3:31])=[C:11]([C:9]#[N:10])[C:16]2[N:17]=[C:18]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[O:... | O=C1CCC(=O)N1Br | C=C(OCC)c1c(C)c(C#N)c2nc(C(=O)N(C)C)oc2c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | 0.33 | Next, at room temperature, N-bromosuccinimide (2.10 g, 11.8 mmol) was added to a tetrahydrofuran/water (178 ml/11 ml) mixed solution of the obtained 4-cyano-6-[1-(ethoxy)ethenyl]-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide (3.56 g, 11.2 mmol), and stirred for 20 minutes. The solvent was evaporated away under... | Cc1c(C(=O)CBr)c(F)c2oc(C(=O)N(C)C)nc2c1C#N | null | null | null |
1,580,437 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12](C(O)=O)[O:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[CH:12][O:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C(O)c1cc(=O)c(OCc2ccccc2)co1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc2ncccc2c1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 5-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (68.9 g, 280 mmol) was added to 300 mL of quinoline at 235° C. and the mixture was heated at reflux for 30 min. The mixture was cooled to room temperature and concentrated to give a residue which was purified by silica gel chromatography to give 3-(benzyloxy)-4H-pyran-4-on... | O=c1ccocc1OCc1ccccc1 | null | null | null |
892,821 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | CN(C)C=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[OH:18])[N:14]=[CH:13][CH:12]=[C:11]2[O:19][C:20]1[C:21]([CH3:30])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:... | COc1cc2c(Oc3cc4ccccc4nc3C)ccnc2cc1O | CCOC(=O)CBr | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 8 | N,N-Dimethylformamide (1.5 ml) was added to 6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (50 mg), ethyl bromoacetate (75 mg), and potassium carbonate (62 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with e... | CCOC(=O)COc1cc2nccc(Oc3cc4ccccc4nc3C)c2cc1OC | null | 49.2 | null |
1,559,286 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | C[O:2][C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:21](=[CH:22][CH:23]=1)[O:20][C:11]1([CH2:16][CH2:15][CH2:14][N:13]([CH:17]([CH3:19])[CH3:18])[CH2:12]1)[CH2:10][C:9]2=[O:24].[OH-].[Na+]>>[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][C:11]2([CH2:10][C:9](=[O:24])[C:8]3[C:21](=[CH:22][CH:23]=[C:6](/[CH:5]=[CH:4]/[C:3](... | COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCCN(C(C)C)C1)O2 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (±)-(E)-3-[1′-Isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (234 mg, 0.681 mmol) was treated with 1 M NaOH according to the procedure described in Example 16 STEP B to give (±)-(E)-3-[1′-isopropyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid. The acid was treated with NH2OT... | CC(C)N1CCCC2(CC(=O)c3cc(/C=C/C(=O)O)ccc3O2)C1 | null | null | null |
910,413 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:45])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([NH:27][C:28]([CH:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])=[O:29])[S:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C... | CC(C)(C)OC(=O)N1CCCC(NC(=O)c2ccc(-c3csc(NC(=O)C4CCCN4C(=O)OCc4ccccc4)n3)cc2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | 3-(4-{2-[(1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-thiazol-4-yl}-benzoylamino)-piperidine-1-carboxylic acid tert butyl ester (Compound 5336, Example 336, 100 mg, 0.16 mmol) was dissolved in 4 mL of 1:1 solution of CH2Cl2/TFA and stirred for 1.5 at room temperature. Reaction mixture was evaporated under reduce... | O=C(NC1CCCNC1)c1ccc(-c2csc(NC(=O)C3CCCN3C(=O)OCc3ccccc3)n2)cc1 | null | null | null |
395,778 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [C:1]1([CH:7]=[CH:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl>C(Cl)(Cl)Cl.CC(O)C>[C:1]1([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=[N+]([O-])C=Cc1ccccc1 | null | null | Cl | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CC(C)O | null | null | null | null | null | null | null | null | null | 25 | 1.5 | 2-Phenylnitroethene (5.12 g, 34.3 mmol, from step 15a) was dissolved in CHCl3 /i-PrOH (410:85 mL) and SiO2 (51.4 g) was added. NaBH4 (5.2 g, 137 mmol) was added in portions, and the mixture was stirred for 90 minutes at room temperature. HCl (0.5N, 100, mL) was added, and the mixture was stirred for 30 minutes. The lay... | O=[N+]([O-])CCc1ccccc1 | null | 75 | null |
968,852 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([NH:28]S(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:16][CH2:17][C:10]=12.[OH-].[Na+]>S(=O)(=O)(O)O>[NH:15]1[C:11]2=[N:12][CH:13]=[CH:14][C:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:28])=[CH:3][C:2]=3[F:1])=[C:10]2[CH2:17][CH2... | Cc1ccc(S(=O)(=O)Nc2ccc(Oc3ccnc4c3CCN4S(=O)(=O)c3ccc(C)cc3)c(F)c2)cc1 | null | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 50 mg (0.09 mmol) of N-[3-fluoro-4-({1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]-4-methylphenylsulfonamide (from example XLV) are dissolved in 1.00 ml of sulfuric acid (95%) and stirred at RT overnight. With ice-cooling, the reaction solution is neutralized with 20% strength aqueo... | Nc1ccc(Oc2ccnc3c2CCN3)c(F)c1 | null | null | null |
326,229 | ord_dataset-8fe3c7256e6747e59933c880f5f642a0 | null | 1996-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][NH2:32])[C:6]=2[CH:33]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C... | CC(=O)OC(C)=O | Cc1ccccc1C(=O)Nc1ccc(C(=O)N2CCCC(CCN)c3cc(Cl)ccc32)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 80 | 2 | To a solution of 7-chloro-5-(2-aminoethyl)-1-[6-(2-methylbenzoyl-amino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.42 g) in pyridine (10 ml) is added acetic anhydride (0.13 ml), and the mixture is stirred at 80° C. for 2 hours, and then stirred at room temperature overnight. Water is added to the reaction solution... | CC(=O)NCCC1CCCN(C(=O)c2ccc(NC(=O)c3ccccc3C)nc2)c2ccc(Cl)cc21 | null | null | null |
1,306,033 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | CON(C)[C:4](=[O:23])[C:5]1[CH:10]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:8]=[C:7]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:6]=1.[CH3:25][Mg]Br.Cl>C1COCC1.O>[N:17]1([C:7]2[CH:6]=[C:5]([C:4](=[O:23])[CH3:25])[CH:10]=[C:9]([S:11]([F:12])([F:16])([F:15])([F:13])[F:14])[CH:8]=2)[CH2:22][CH2:21][O:2... | C[Mg]Br | CON(C)C(=O)c1cc(N2CCOCC2)cc(S(F)(F)(F)(F)F)c1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 2 | N-Methoxy-N-methyl-3-morpholin-4-yl-5-(pentafluorosulfanyl)benzamide (2.38 g) was dissolved in THF (50 ml), methylmagnesium bromide (4.22 ml, 3 M in ether) was added dropwise at 0° C. and then the mixture was stirred at RT for 2 h. Then 1N hydrochloric acid (100 ml) was added, and the mixture was diluted with water and... | CC(=O)c1cc(N2CCOCC2)cc(S(F)(F)(F)(F)F)c1 | null | null | null |
852,275 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([O:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.[F:21][C:22]([F:36])([C:27]1[NH:31][C:30]2[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=2[N:28]=1)[C:23]([F:26])([F:25])[F:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:19]([O:18][CH:12]([CH2... | CCOC(=O)C(Cc1ccc(OCCBr)cc1)OCC | FC(F)(F)C(F)(F)c1nc2ccccc2[nH]1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate (371 mg, 1 mmol), 2-(pentafluoroethyl)-1H-benzimidazole (259 mg, 1.1 mmol), K2CO3 (552 mg, 4 mmol) and DMF (5 ml) using the procedure described in Step B of Example 1. Yield 420 mg (84%). | CCOC(=O)C(Cc1ccc(OCCn2c(C(F)(F)C(F)(F)F)nc3ccccc32)cc1)OCC | null | null | null |
482,562 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[O:22]>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:29][C:26]1[C... | O=C(c1ccc(O)cc1)c1cccs1 | COc1cc2nccc(Cl)c2cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 160 | 0.67 | 4-Chloro-6,7-dimethoxyquinoline (112 mg) and 4-hydroxyphenyl 2-thienyl ketone (102 mg) obtained in Example 39 were mixed and stirred at 160° C. for 40 minutes. The reaction mixture was purified in the same manner as described in Example 24 to obtain 34 mg of the title compound (yield: 17%). | COc1cc2nccc(Oc3ccc(C(=O)c4cccs4)cc3)c2cc1OC | null | 17.4 | null |
469,826 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [CH:1]1([CH2:4][C:5]2[C:13]3[O:12][N:11]=[C:10]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:9]=3[CH:8]=[CH:7][C:6]=2[OH:20])[CH2:3][CH2:2]1.[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:1]1([CH2:4][C:5]2[C:13]3[O:12][N:11]=[C:10]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[CH... | BrCCCBr | Oc1ccc2c(-c3ccccc3)noc2c1CC1CC1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 7-cyclopropylmethyl-3-phenyl-6-hydroxybenz-[4,5]-isoxazole (0.25 grams) in 2-butanone (3.0 mL) was treated with 1,3-dibromopropane (0.48 mL) and potassium carbonate (0.50 grams). The mixture was refluxed for 4 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The organ... | BrCCCOc1ccc2c(-c3ccccc3)noc2c1CC1CC1 | null | null | null |
232,513 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:14]>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][CH2:11][CH2:10][S:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:20][CH:19]=1 | Cc1ccc(S)cc1 | O=C(CCCCl)c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound (58.0 g, 100%) was prepared from 4-thiocresol and 4-chloro-4'-fluorobutyrophenone as described in Example 2 as an oil; IR(neat): C=O @ 1700 cm-1 ; NMR(DMSO-d6, TMS): δ 1.8-1.95(m,2H, CH2), 2.26(s,3H,ArCH3), 2.98(t,2H,CH2 --CO), 3.16(t,2H,S--CH2), 7.1-8.1(m,8H, aromatic); mass spectrum m/e 288. | Cc1ccc(SCCCC(=O)c2ccc(F)cc2)cc1 | null | 100 | null |
522,271 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([S:30](C)(=[O:32])=[O:31])=[CH:26][CH:25]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[NH3:34]>O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][C:17]3[CH:22]=[... | N | CS(=O)(=O)c1ccc(-c2cnn(-c3ccc(F)c(F)c3)c(=O)c2Oc2ccc(F)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 109 was converted to the title sulfonamide according to the method of Example 384 (yield: 110 mg, 45.7%). mp 224-226° C. 1H NMR (300 MHz, CDCl3) δ 4.86 (br s, 2H), 6.89-7.03 (m, 4H), 7.19-7.30 (m, 1H), 7.45-7.52 (m, 1H), 7.56-7.66 (m, 1H), 7.79 (d, J=9 Hz, 2H), 8.04 (d, J=9 Hz, 1H), 8.08 (s, 1H... | NS(=O)(=O)c1ccc(-c2cnn(-c3ccc(F)c(F)c3)c(=O)c2Oc2ccc(F)cc2)cc1 | null | null | null |
269,567 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | [N:1]12[CH2:8][C:5]([C:9](N(OC)C)=[O:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[CH3:15][Li]>CCOCC>[C:9]([C:5]12[CH2:8][N:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2)(=[O:10])[CH3:15] | CON(C)C(=O)C12CCCN(CC1)C2 | [Li]C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | -10 | 1 | A solution of (±) 1-azabicyclo[3.2.1]oct-5-yl-N-methyl-N-methoxycarboxamide (D3) (22.0 g; 0.11 mole) in dry ether (500 ml) was cooled to -30° C. under nitrogen and treated dropwise with methyl lithium (80.0 ml of a 1.4 M solution in diethyl ether; 0.11 mole). The rate of addition was controlled to ensure that the tempe... | CC(=O)C12CCCN(CC1)C2 | null | null | null |
628,970 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [OH:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][CH2:9][N:8]2[CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[CH:4][C:3]=1[O:34][CH3:35].[CH2:36](Br)[CH:37]=[CH2:38]>>[CH2:38]([O:1][C:2]1[CH:33]=[CH... | COc1cc(CC2c3cc(OC)c(OC)cc3CCN2CC(=O)NCc2ccccc2)ccc1O | C=CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared by reaction of 2-[1-(4-hydroxy-3-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide with allyl bromide | C=CCOc1ccc(CC2c3cc(OC)c(OC)cc3CCN2CC(=O)NCc2ccccc2)cc1OC | null | null | null |
1,617,761 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[O:8])([O-:3])=[O:2].[F:23][C:24]([F:51])([O:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][CH2:46][C:47]([F:50])([F:49])[F:48])=[CH:39][CH:38]=1)[C:25]1[CH:30]=[CH:29][... | O=C(O)/C=C/c1ccc(C(F)(F)Oc2ccc(OCCCC(F)(F)F)cc2)cc1 | O=C(OCCCCCCO)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 1 | 3.68 g (11.8 mmol) of 6-hydroxyhexyl 3,5-dinitrobenzoate, 4.91 g (11.8 mmol) of (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}phenyl)prop-2-enoic acid, 144 mg (1.2 mmol) of 4-dimethylaminopyridine are dissolved in 30 mL of dichloromethane. 2.48 g (13.0 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimi... | O=C(/C=C/c1ccc(C(F)(F)Oc2ccc(OCCCC(F)(F)F)cc2)cc1)OCCCCCCOC(=O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1 | null | 81.7 | null |
780,649 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | [OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-].C1CCCCC=1>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1 | [O-][n+]1ccccc1NCCCO | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | C1=CCCCC1 | null | null | null | null | null | null | null | null | null | null | 48 | A mixture of 2-(3-hydroxypropyl)aminopyridine N-oxide (3.0 g, 17.9 mmol), as prepared in the preceding step, cyclohexene (10 ML, 100 mmol), and 10% palladium(0) on carbon (300 mg) in ethanol (50 mL) was heated to reflux. After two days, the reaction mixture was cooled. The catalyst was removed by filtration through Cel... | OCCCNc1ccccn1 | null | 88.1 | null |
1,671,521 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:17]1[C:18]2[CH:25]=[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[S:23][C:19]=2[N:20]=[CH:21][N:22]=1>C1COCC1>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([O:13][C:17]3[C:18]4[... | CC(C)(C)OC(=O)NCCc1cc2c(Cl)ncnc2s1 | OC1CCC(N2CCOCC2)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 4-(morpholin-4-yl)cyclohexan-1-ol (143 mg, 0.77 mmol, 1.10 equiv) in THF (20 mL) was added sodium hydride (140 mg, 3.50 mmol, 5.00 equiv, 60% dispersion in mineral oil) at 0° C. The solution was stirred for 30 min at room temperature under nitrogen. Then tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-... | CC(C)(C)OC(=O)NCCc1cc2c(OC3CCC(N4CCOCC4)CC3)ncnc2s1 | null | 39.2 | null |
1,687,188 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH2:14])[N:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>>[Br:15][C:13]1[N:12]=[N:11][C:10]([NH2:14])=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1 | O=C1CCC(=O)N1Br | Nc1nncc(-c2ccc(F)cc2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 6-Bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1.95 g, 49%) was prepared from 5-(4-fluorophenyl)-1,2,4-triazin-3-amine (2.8 g, 14.00 mmol) and N-bromosuccinimide (7.87 g, 44.00 mmol) according to the general procedure of Preparation 3. | Nc1nnc(Br)c(-c2ccc(F)cc2)n1 | null | 51.8 | null |
1,361,315 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]1[CH:20]=[C:19]([CH:21]=[C:22]2[S:26][C:25](SC)=[N:24][C:23]2=[O:29])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[F:1][C:2]1[CH:20]=[C:19]([CH:21]=[C:22]2[S:26][C:25]([N:30]3[CH2:35][CH2:34][O:33... | C1COCCN1 | CSC1=NC(=O)C(=Cc2ccc(Oc3ccc(C#N)cc3C(F)(F)F)c(F)c2)S1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-[2-Fluoro-4-(2-morpholin-4-yl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenoxy]-3-trifluoromethyl-benzonitrile was prepared using 4-[2-Fluoro-4-(2-methylsulfanyl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenoxy]-3-trifluoromethyl-benzonitrile and morpholine as described in Example 5C. 1H NMR (400 Hz, DMSO-d6) δ 8.40 (bs, 1H), 8.10... | N#Cc1ccc(Oc2ccc(C=C3SC(N4CCOCC4)=NC3=O)cc2F)c(C(F)(F)F)c1 | null | null | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.