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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,690,620 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH2:16]Cl)[CH:15]=1.[H-].[Na+]>>[Br:9][C:10]1[CH:15]=[C:14]([CH2:16][N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)[CH:13]=[N:12][CH:11]=1 | O=S1(=O)CCNCC1 | ClCc1cncc(Br)c1 | null | [H-] | [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 | null | null | In analogy to the procedure described for the preparation of intermediates A-12 [B], thiomorpholine 1,1-dioxide was reacted with 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A]) in the presence of NaH to give the title compound as a white solid. MS: 304.9, 307.0 (M+H+). | O=S1(=O)CCN(Cc2cncc(Br)c2)CC1 | null | null | null |
750,336 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Se](=O)=[O:13]>O1CCOCC1>[C:2]1([CH:1]=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1 | O=[Se]=O | Cc1nccc2ccccc12 | null | null | null | null | 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 | 25 | null | In 1,4-dioxane (20 ml) was dissolved 1-methylisoquinoline (300 mg, 2.10 mmol). To the resulting solution was added selenium dioxide (323 mg, 2.91 mmol), followed by heating under reflux for 1.5 hours under a nitrogen gas stream. After cooling to room temperature, the reaction mixture was filtered through Celite. The fi... | O=Cc1nccc2ccccc12 | null | 76.4 | null |
1,211,846 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]2[C:23]3[C:18](=[CH:19][C:20]([I:24])=[CH:21][CH:22]=3)[C:17](=[O:25])[C:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:15]2)[CH2:9]1)=O)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[CH2:29]([O:28][C:26]([C:16]1[C:17](=[O:25])[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([I:24])[CH:19]=2)... | CCOC(=O)c1cn(C[C@H]2CCN(C(=O)OC(C)(C)C)C2)c2ccc(I)cc2c1=O | null | null | Cl | null | null | 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 | 25 | 1 | The crude (R)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 95, ˜4.4 mmol) was dissolved in 1,4-dioxane (20 mL) and 4.0M hydrogen chloride in 1,4-dioxane (20 mL) was added. The reaction mixture was stirred at room temperature for 1 h, and the solv... | CCOC(=O)c1cn(C[C@@H]2CCNC2)c2ccc(I)cc2c1=O | null | null | null |
1,410,910 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]([C:26](N(OC)C)=[O:27])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:32][Mg]Br>O1CCCC1>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:16]([C:26](=[O:27])[CH3:32])=[... | C[Mg]Br | CON(C)C(=O)c1cc(Cl)c2cccnc2c1N1CCC(O[Si](C)(C)C(C)(C)C)CC1 | 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 | To a mixture of 8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide (312 mg, 0.672 mmol) in tetrahydrofuran (0.9 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (2.9 mL, 4.0 mmol). The reaction was stirred at room temperature overnight, then quenched wi... | CC(=O)c1cc(Cl)c2cccnc2c1N1CCC(O[Si](C)(C)C(C)(C)C)CC1 | null | 98 | null |
942,314 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[N:12]=[C:13]([NH2:25])[C:14]2[N:15]([N:17]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:16]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[N:12]=[C:13]([NH2:25])[C:14]2[N:15]([N:17]=[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:16]=1 | CC(C)(C)OC(=O)NCC#Cc1cn2nc(-c3ccco3)nc2c(N)n1 | 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 | To a solution of [3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-prop-2-ynyl]-carbamic acid tert-butyl ester (100 mg, 0.28 mmol; see Ex. 41 below which was prepared according to Example 3 above) in CH2Cl2 (3 mL) was added trifluoroacetic acid (107 uL, 1.4 mmol). The reaction was stirred at room temperature... | NCC#Cc1cn2nc(-c3ccco3)nc2c(N)n1 | null | null | null |
594,661 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [CH2:1]([N+:5]([O-:7])=[O:6])/[CH:2]=[N:3]\O.Cl.N[C:10]1[C:17]([F:18])=[C:16]([Cl:19])[C:15]([F:20])=[CH:14][C:11]=1[CH:12]=O>C(O)C>[Cl:19][C:16]1[C:17]([F:18])=[C:10]2[C:11]([CH:12]=[C:1]([N+:5]([O-:7])=[O:6])[CH:2]=[N:3]2)=[CH:14][C:15]=1[F:20] | Nc1c(C=O)cc(F)c(Cl)c1F | O=[N+]([O-])C/C=N\O | null | Cl | null | 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 | 35 | 16 | 17.4 g of methazonic acid and 60 cm3 of a 37% aqueous hydrochloric acid solution were rapidly added, with stirring, to a solution of 8.7 g of 2-amino-4-chloro-3,5-difluorobenzaldehyde in 300 cm3 of ethanol, while the mixture was maintained at a temperature in the region of 35° C. The mixture was stirred for 16 hours at... | O=[N+]([O-])c1cnc2c(F)c(Cl)c(F)cc2c1 | null | 72.9 | null |
1,486,977 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:47])=[C:8]([N:10]2[CH2:46][CH2:45][C:13]3[N:14]=[C:15]([C:25]4[CH:33]=[CH:32][CH:31]=[C:30]5[C:26]=4[C:27]([CH3:44])=[CH:28][N:29]5[S:34]([C:37]4[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=4)(=[O:36])=[O:35])[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][NH:21][C@H:20]([CH3:24])[CH2:19]4)... | Cc1ccc(S(=O)(=O)n2cc(C)c3c(-c4nc5c(c(N6CCN[C@H](C)C6)n4)CN(c4cc(C(C)C)ccc4C)CC5)cccc32)cc1 | O=C1COC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | A mixture of (R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (53 mg, 0.082 mmol), oxetan-3-one (17.6 mg, 0.245 mmol) and Na(AcO)3BH (51.9 mg, 0.245 mmol) in DCM (3 mL) was stirred at rt for 3 h. At that point starting material re... | Cc1ccc(S(=O)(=O)n2cc(C)c3c(-c4nc5c(c(N6CCN(C7COC7)[C@H](C)C6)n4)CN(c4cc(C(C)C)ccc4C)CC5)cccc32)cc1 | null | null | null |
764,403 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH:9]=[CH:10][CH3:11].[NH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:20])[CH2:14][CH2:13]1>CN(C)C=O>[CH2:8]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:2... | O=C(NC1CCNCC1)c1ccc2[nH]ncc2c1 | CC=CCCl | 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 | 25 | 20 | Potassium carbonate (55.0 mg, 0.398 mmol) and 1-chloro-2-butene (17.8 mg, 0.197 mmol) were added to a solution of the N-(4-piperidinyl)-1H-indazole-5-carboxamide (40.0 mg, 0.164 mmol) obtained in Example 58 in N,N-dimethylformamide (1.2 ml), and the resulting mixture was stirred for 20 hours while being maintained at r... | CC=CCN1CCC(NC(=O)c2ccc3[nH]ncc3c2)CC1 | null | 53.1 | null |
812,721 | ord_dataset-892acf7477db4d3a8a8559f004a7c0a2 | null | 2008-01-01T00:03:00 | true | CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:34])[C@H:16]([CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=1)[NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].[C:35]1([C:41]2[O:42][C:43]3[C:49]([CH2:50]O)=[CH:48][CH:47]=[CH:46][C:44]=3[N:45]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(P(... | COC(=O)[C@H](Cc1cc(Cl)c(O)c(Cl)c1)NC(=O)C(F)(F)F | OCc1cccc2nc(-c3ccccc3)oc12 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 60 | Diethylazodicarboxylate (40% toluene solution 0.63 ml) was added dropwise to a solution of 3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (252 mg, 0.7 mmol), [(2-phenyl)-benzoxazol-7-yl]methanol (193 mg, 0.857 mmol) and triphenylphosphine (374 mg, 1.43 mmol) in tetrahydrofuran (3 ml) under argon atmosphere at 5... | COC(=O)[C@H](Cc1cc(Cl)c(OCc2cccc3nc(-c4ccccc4)oc23)c(Cl)c1)NC(=O)C(F)(F)F | null | 81.6 | null |
349,205 | ord_dataset-66f304805e5d47fc8d3c722b1bd8dfa2 | null | 1996-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[C:16](OCC)(=[O:23])[CH2:17][C:18]([O:20]CC)=[O:19]>>[O:23]=[C:16]1[C:17]([C:18]([OH:20])=[O:19])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:1]1 | Nc1ccccc1C(=O)c1ccccn1 | CCOC(=O)CC(=O)OCC | 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 | 180 | null | A mixture of 2-(2-aminobenzoyl)pyridine (4.36 g), diethyl malonate (3.92 ml) and 1,9-diazabicyclo[5.4.0]-7-undecene(0.5 ml) was heated for 3 hours at 180° C. The reaction mixture was cooled to give ethyl ester of 1,2-dihydro-2-oxo-4-(2-pyridyl)-3-quinolinecarboxylic acid as crystals (6.1 g: unrefined). The crystalline ... | O=C(O)c1c(-c2ccccn2)c2ccccc2[nH]c1=O | null | null | null |
1,740,446 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[F:8].S(Cl)([Cl:16])=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([Cl:16])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8] | O=C(O)C=Cc1ccc(F)c(Br)c1 | O=S(Cl)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 | 100 | 2 | 3-(3-Bromo-4-fluoro-phenyl)-acrylic acid (3.3 g, 13.3 mmol) prepared in Step 1 was added to thionyl chloride (10.0 mL). The reaction mixture was stirred at 100° C. for 2 hours, concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to gi... | O=C(Cl)C=Cc1ccc(F)c(Br)c1 | null | null | null |
3,244 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [OH:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]=1[S:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[OH:20]O>C(O)(=O)C>[OH:10][C:4]1[CH2:5][C:6]([CH3:8])([CH3:9])[CH2:7][C:2](=[O:1])[C:3]=1[S:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:20] | Cc1ccc(CSC2=C(O)CC(C)(C)CC2=O)cc1 | OO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0 | 24 | A mixture of 3-hydroxy-5,5-dimethyl-2-(p-methylbenzylthio)-2-cyclohexen-1-one (10 g., 0.036 mole), 30 percent hydrogen peroxide (4.11 g., 0.0362 mole), and 100 ml. of glacial acetic acid was allowed to stand at room temperature for 24 hours. The solution was poured into ice water, and the resulting pink solid was filte... | Cc1ccc(CS(=O)C2=C(O)CC(C)(C)CC2=O)cc1 | null | null | null |
1,382,675 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.[CH:8]1([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[CH:28]=[N:27][CH:26]=[CH:25][C:21]=3[C:22](O)=[O:23])=[O:18])[C:14]([NH:29][C:30]3[CH:31]=[N:32][CH:33]=[N:34][CH:35]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1>>[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:22]([C:21]1[CH... | O=C(O)c1ccncc1NC(=O)c1nc(C2CC2)ccc1Nc1cncnc1 | OCC1CCCN1 | 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 | According to the general method described in step 3 of example 53, reaction of 2-hydroxymethylpyrrolidine with 3-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-isonicotinic acid provided the title compound as off-white solid (29%). | O=C(Nc1cnccc1C(=O)N1CCCC1CO)c1nc(C2CC2)ccc1Nc1cncnc1 | null | 29 | null |
1,471,509 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[CH3:9] | Cc1ccc(F)cc1F | O=[N+]([O-])O | null | O=S(=O)(O)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 | 45 | 1 | To a stirred solution of 2,4-difluorotoluene (25.0 g, 195.3 mmol) in conc. H2SO4 (60 mL) was added fuming HNO3 (30 mL) drop wise at the rate that temperature was maintained between 40-50° C. over a period of 1.5 h. The reaction mixture was stirred at 40° C. for an additional 1 h. The reaction mixture was poured into ic... | Cc1c(F)cc(F)cc1[N+](=O)[O-] | null | 62 | null |
541,327 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[O:26]CC=C)=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30]1(OC2C=CC=CC=2)[CH:35]=CC=C[CH:31]=1>>[CH2:35]([C:21]1[C:20]2[O:26][C:16]([CH2:15][C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])... | C=CCOc1ccc(Cl)cc1NC(=O)Cc1ccc(OC)c(OC2CCCC2)c1 | c1ccc(Oc2ccccc2)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 | A solution of N-(3-cyclopentyloxy-4-methoxyphenylacetyl)-2-allyloxy-5-chloroaniline (38.1 g, 0.092 mol) in 200 ml of diphenyl ether was heated under nitrogen at 180° for 8 hours. Protracted heating resulted in reduced yields. The reaction mixture was diluted with 500 ml of petroleum ether, applied to a column packed wi... | C=CCc1cc(Cl)cc2nc(Cc3ccc(OC)c(OC4CCCC4)c3)oc12 | null | 52 | null |
501,202 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][NH:6]1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>>[CH3:2][O:3][C:4](=[O:11])[C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20] | COC(=O)[C@H]1C[C@@H](O)CN1 | O=[N+]([O-])c1ccccc1F | 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 | The same procedures used in Reference Example 1 were repeated except for using the cis-4-hydroxy-D-proline methyl ester hydrochloride prepared in Reference Example 4 and 1-fluoro-2-nitrobenzene to give the title compound. Yield 97.2%. | COC(=O)[C@H]1C[C@@H](O)CN1c1ccccc1[N+](=O)[O-] | null | 97.2 | null |
1,214,643 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:14](=O)[CH3:15])[C:6](=O)[CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:2].O.[NH2:19][NH2:20]>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]([CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N:19][NH:20][C:14]=1[CH3:15])=[O:17])[CH3:2] | CCOC(=O)C(C(C)=O)C(=O)COC(C)(C)C | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 2-acetyl-4-tert-butoxy-3-oxo-butyric acid ethyl ester [0.325 g, Reference Example 46] in acetic acid (3 ml) was added hydrazine hydrate (71 μL). The mixture was stirred at ambient temperature for 16 hours and then evaporated to remove the acetic acid. The residue was dissolved in ethyl acetate and the ... | CCOC(=O)c1c(COC(C)(C)C)n[nH]c1C | null | null | null |
671,067 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([NH:20][C:21](=[O:23])[CH3:22])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1.[H-].[Na+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[... | CC(=O)Nc1cncc(N2CCN(C(=O)OC(C)(C)C)CC2)n1 | Clc1cccc(CBr)c1 | 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 | 25 | 4 | To a solution of 6′-acetylamino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-5b (36.9 mg, 0.11 mmol) and 1-bromomethyl-3-chloro-benzene (15.8 μL, 0.12 mmol) in DMF (1.1 mL) at room temperature was added 60% NaH in mineral oil (5 mg, 0.13 mmol). After stirring at room temperature for 4 h, th... | CC(=O)N(Cc1cccc(Cl)c1)c1cncc(N2CCN(C(=O)OC(C)(C)C)CC2)n1 | null | null | null |
1,057,238 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | COC1C=C(OC)C=CC=1C[O:6][N:7]1[C:12](=[O:13])[C:11]2[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10]=2[NH:9][C:8]1=[O:21].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>>[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:9]2[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[O:14][C:11]=3[C:12](=... | BrCc1ccc(Br)cc1 | COc1ccc(COn2c(=O)[nH]c3c(oc4ccccc43)c2=O)c(OC)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 | Following general procedure B2 and D1, 3-(2,4-dimethoxy-benzyloxy)-1H-benzo[4,5]furo[3,2-d]pyrimidine-2,4-dione was alkylated with 4-bromobenzyl bromide and subsequently deprotected to provide the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 5.52 (s, 2H); 7.29-7.40 (m, 3H); 7.52 (d, J=8 Hz, 2H); 7.60 (d... | O=c1c2oc3ccccc3c2n(Cc2ccc(Br)cc2)c(=O)n1O | null | null | null |
977,547 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[C:6]([CH:9]=1)[CH2:7]Cl.[CH:14]1([CH2:17][CH2:18][NH:19][C:20]([C:22]2[N:23]=[N:24][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:26][CH:27]=2)=[O:21])[CH2:16][CH2:15]1>>[CH:14]1([CH2:17][CH2:18][NH:19][C:20]([C:22]2[N:23]=[N:24][C:25]([N:28]3[CH... | Fc1ccc(C(F)(F)F)c(CCl)c1 | O=C(NCCC1CC1)c1ccc(N2CCNCC2)nn1 | 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 | Following the procedure of Example 11, making variations only as required to use 5-fluoro-2-trifluoromethylbenzyl chloride in place of 2-trifluoromethylbenzyl chloride to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide, the title compound was obtained as a white solid (40% yield). 1H ... | O=C(NCCC1CC1)c1ccc(N2CCN(Cc3cc(F)ccc3C(F)(F)F)CC2)nn1 | null | null | null |
745,366 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10] | O=Cc1ccccc1-c1cnccn1 | null | null | [BH4-] | [Na+] | 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 | 25 | 2 | To a stirred suspension of 2-pyrazin-2-ylbenzaldehyde (9.9 mmol from the previous step) in absolute MeOH (100 mL) at 0° C. was added sodium borohydride (420 mg, 11.1 mmol) in portions. The mixture was allowed to warm to room temperature and stirred under N2 atmosphere for 2 h. The solvent was removed in vacuo and the r... | OCc1ccccc1-c1cnccn1 | null | null | null |
1,273,562 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=O)[C:5]=12.[K+].[Br-]>>[CH3:10][C:6]1[C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=[CH:8][CH:7]=1 | O=Cc1cccn2ccnc12 | null | null | [Br-] | [K+] | 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 | From 4a (yield: 10%); mp: 150-152° C.; IR (KBr) 2100, 1700, 1600, 1280 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), ... | Cc1cccn2ccnc12 | null | 10 | null |
479,240 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[C:7]1[N:8]=[C:9]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:15]([CH3:16])=[C:14]([CH3:17])[S:13][C:11]=2[N:12]=1>>[N:1]1([C:7]2[N:8]=[C:9]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:10]3[C:15]([CH3:16])=[C:14]([CH3:17])[S:13][C:11]=... | Cc1sc2nc(Cl)nc(NCc3ccccc3)c2c1C | 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 | Following the procedure of Example 97, the reaction of pyrazole with 2-chloro-5,6-dimethyl-4-benzylamino-thieno-[2,3-d]-pyrimidine gives 2-(pyrazol-1-yl)-5,6-dimethyl-4-benzylamino-thieno-[2,3-d]-pyrimidine. | Cc1sc2nc(-n3cccn3)nc(NCc3ccccc3)c2c1C | null | null | null |
1,345,548 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH3:30].[Li+].[Br-].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[CH:22]=... | [Li]C | O=C(c1cccc(-c2ccccc2)n1)c1ccccc1OCc1ccccc1 | null | [Br-] | [Li+] | 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 | -90 | 0.33 | To a solution of 11.7 g (32.0 mmol) of 17 in 260 mL of THF, 37 mL (33.6 mmol) of 0.91 M MeLi*LiBr in THF was added dropwise with vigorous stirring for 20 min at −90° C. The reaction mixture was slowly warmed to room temperature and 50 mL of water was added. The organic solvent was evaporated using a rotary evaporator. ... | CC(O)(c1cccc(-c2ccccc2)n1)c1ccccc1OCc1ccccc1 | null | 98.3 | null |
1,357,800 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[C@@H:11]([NH:13]C(=O)OC(C)(C)C)[CH3:12]>CC(O)=O>[F:8][C:7]1[C:2]2[NH:1][C:10]([C@@H:11]([NH2:13])[CH3:12])=[N:9][C:3]=2[CH:4]=[CH:5][CH:6]=1 | C[C@H](NC(=O)OC(C)(C)C)C(=O)Nc1cccc(F)c1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | 0.67 | A stirred solution of (S)-tert-butyl 1-(2-amino-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate (2.08 g, 7.00 mmol) in AcOH (30 mL) was heated at 65° C. for 2 h, cooled to rt. After being concentrated under reduced pressure, the residue was subjected to 4 M HCl in 1,4-Dioxane (20 mL). The resultant mixture was stirred a... | C[C@H](N)c1nc2cccc(F)c2[nH]1 | null | null | null |
1,174,573 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][NH:6][C:7](=[O:12])[C:8](Br)([CH3:10])[CH3:9].[Cl:14][C:15]1[C:20]([OH:21])=[CH:19][C:18]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[C:17]([F:35])[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:... | Cn1c(C(F)(F)F)cc(=O)n(-c2cc(O)c(Cl)cc2F)c1=O | COC(=O)CCNC(=O)C(C)(C)Br | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC#N | null | null | null | null | null | null | null | null | null | null | null | 3-(2-Bromo-2-methylpropionylamino)propionic acid methyl ester (224 mg) and 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (250 mg) were dissolved in acetonitrile 5 ml. After addition of K2CO3 (204 mg), the reaction mixture was heated for 12 hours under reflux, cooled and diluted... | COC(=O)CCNC(=O)C(C)(C)Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1Cl | null | 63.8 | null |
1,035,396 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [C:1](#[N:3])[CH3:2].C([Li])(C)(C)C.[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([O:21]C)=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1>C1COCC1>[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19](=[O:21])[CH2:2][C:1]#[N:3])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1 | CC#N | COC(=O)c1ccc2cnccc2c1 | null | [Li]C(C)(C)C | 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 | 0.33 | To a solution of ACN (1.8 g, 43 mmol) in 90 mL of THF at −78° C. was added tert-butyllithium (25 mL, 1.7 M in heptane). After 20 minutes, methyl isoquinoline-6-carboxylate (2.0 g, 11 mmol) was added slowly in 10 mL of THF. After 1 hour, the reaction was quenched with 100 mL of aqueous NH4Cl and warmed to room temperatu... | N#CCC(=O)c1ccc2cnccc2c1 | null | 97.3 | null |
1,045,689 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].C(N(C(C)C)C(C)C)C.Cl[CH2:23][O:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][CH2:23][O:24][CH3:25] | COCCl | Oc1cccc2c(F)cccc12 | null | O=C([O-])[O-] | [Na+] | 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 | 0.5 | A solution of 0.257 g of 5-fluoro-1-hydroxynaphthalene in 6 ml of dry dichloromethane was cooled in an ice/salt bath after which was added 0.36 ml (2.07 mmol) of ethyl diisopropylamine followed by 0.15 ml (0.16 g, 1.96 mmol) of chloromethylmethyl ether. The mixture was stirred at 0° C. for 0.5 h after which it was allo... | COCOc1cccc2c(F)cccc12 | null | 79.6 | null |
772,916 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:19][C:20]4[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=4)=[O:18])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH:19][C:20]4[CH... | COC(=O)c1ccc(NC(=O)c2ccc3[nH]nc(-c4ccc(F)cc4)c3c2)cc1 | null | null | [Na+] | [OH-] | null | 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 | 25 | 2 | To a solution of methyl 4-{[3-(4-fluorophenyl)-1H-indazol-5-yl]carbonylamino}benzoate (112 mg, 0.29 mmol) in methanol (20 mL) and water (20 mL) was added sodium hydroxide (25 mg, 0.64 mmol). The solution was stirred at room temperature for 2 hours when it was acidified and the methanol removed under vacuo. The resultin... | O=C(O)c1ccc(NC(=O)c2ccc3[nH]nc(-c4ccc(F)cc4)c3c2)cc1 | null | null | null |
1,267,968 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]3)[N:15]2[CH3:18])=[C:11]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:10]=1.[C:36](O)(=O)[CH3:37]>>[CH3:18][N:15]1[C:14]([CH2:19][N:... | Cn1c(CN2CCC(C(C)(C)O)CC2)nc2c(N3CCOCC3)nc(Nc3ccccc3N)nc21 | CC(=O)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 | A mixture of 2-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (177 mg, 0.368 mmol) in acetic acid (1.5 mL) was stirred at reflux for 5 hours. The reaction mixture was then concentrated and then purified first by flash chromatography (10% MeOH in DCM containing 1% 2 M a... | Cc1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CCC(C(C)(C)O)CC3)n(C)c2n1 | null | 21.1 | null |
454,772 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH2:11][CH2:10]1.[NH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34]>C(O)COCCO>[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[... | Cc1cc(F)ccc1N1CCc2c(Cl)nc3c(OCC(F)(F)F)cccc3c21 | NCCCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | OCCOCCO | null | null | null | null | null | null | null | null | null | null | null | null | 1-(2-Methyl-4-fluorophenyl)-4-chloro-6-β,β,β-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(600 mg, 1.4 mmol) was dissolved in diethylene glycol(10 ml) and 4-amino-1-butanol(4 ml) was added. The reaction mixture was reacted at the same condition of Step 3 in the Example 42 to obtain 550 mg of desired compound as so... | Cc1cc(F)ccc1N1CCc2c(NCCCCO)nc3c(OCC(F)(F)F)cccc3c21 | null | null | null |
974,493 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2 | Fc1cccc2cc[nH]c12 | null | null | [BH3-]C#N | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 1 | 7-fluoroindole (2.0 g, 14.8 mmol) was dissolved in acetic acid (6 mL) and sodium cyanoborohydride (1.87 g, 29.6 mmol) was added in 5 portions. The mixture was stirred for 1 hour then poured into 150 mL of 2N NaOH. The mixture was extracted with methylene chloride. The organics were combined, washed with brine, dried ov... | Fc1cccc2c1NCC2 | null | 54.2 | null |
346,608 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=1)[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=... | COc1cccc(C(N)COc2noc3ccc(Cl)cc23)c1 | null | null | BrB(Br)Br | 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 | null | null | To a solution of 2.3 g of 3-[2-amino-2-(3-methoxyphenyl)ethoxy]-5-chloro-1,2-benzoisoxazole in 20 ml of methylene chloride is dropwise added 22 ml of a methylene chloride solution (1.0M) of boron tribromide over 15 minutes with ice-cooling, and they are subjected to reaction at the same temperature for 30 minutes. Subs... | NC(COc1noc2ccc(Cl)cc12)c1cccc(O)c1 | null | null | null |
1,243,595 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C(O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[N:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)([O-:14])=[O:13] | O=Cc1cccc([N+](=O)[O-])c1 | Nc1ccc(C(F)(F)F)cc1 | null | null | null | 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 | 25 | null | A mixture of 4-trifluoromethyl-phenylamine (2.6 mL, 21 mmol) and 3-nitro-benzaldehyde (3.44 g, 23 mmol) in ethanol (100 mL) was prepared. The reaction mixture was heated to reflux for 3 h. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to aff... | O=[N+]([O-])c1cccc(C=Nc2ccc(C(F)(F)F)cc2)c1 | null | 95.2 | null |
1,353,375 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | Cl[C:2]1[C:7]2[CH:8]3[O:15][CH2:14][CH2:13][N:9]3[C:10](=[O:12])[NH:11][C:6]=2[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:36])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[C:32]([F:35])([F:34])[F:33])=[CH:19][CH:18]=1.Cl.O1CCOCC1>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][... | O=C1Nc2nccc(Cl)c2C2OCCN12 | Nc1ccc(NC(=O)c2ccc(F)cc2C(F)(F)F)cc1 | null | Cl | null | null | 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 | null | 1 | 42 (16 mg, 0.07 mmol), N-(4-aminophenyl)-4-fluoro-2-(trifluoromethyl) benzamide (22 mg, 0.07 mmol), and 4.0M HCl in dioxane (18 μl, 0.07 mmol) were suspended in a sealed tube, and placed in microwave at 140° C. for 1 h. The crude product was purified directly via HPLC to provide 43. LC-MS (M+H=488, obsd.=488). | O=C(Nc1ccc(Nc2ccnc3c2C2OCCN2C(=O)N3)cc1)c1ccc(F)cc1C(F)(F)F | null | null | null |
760,283 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | C[O-].[Na+].C([C@@H]1CC[C@@H](C)C[C@H]1OC([N:17]1[CH:22]=[CH:21][C:20](=[O:23])[CH2:19][C@@H:18]1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH3:31])=O)(C)C>CO>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C@H:18]2[CH2:19][C:20](=[O:23])[CH:21]=[CH:22][NH:17]2)=[C:25]([CH3:31])[CH:26]=1 | Cc1cc(F)ccc1[C@H]1CC(=O)C=CN1C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C | null | null | C[O-] | [Na+] | 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 | Sodium methoxide (100 mg) was added to a solution of intermediate 6b (170 mg) in MeOH (15 mL) under a nitrogen atmosphere. The mixture was refluxed for two hours and the solvent was removed in vacuo. The residue was partitioned between water (10 mL) and AcOEt (15 mL). The layers were separated, and the aqueous phase wa... | Cc1cc(F)ccc1[C@H]1CC(=O)C=CN1 | null | 161 | null |
658,142 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | [C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([OH:3])=[O:2]>S(=O)(=O)(O)O>[O:13]=[C:11]1[C:6]2[C:7](=[CH:14][CH:15]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[O:8][CH2:9][CH2:10]1 | O=C(O)CCOc1ccc(C(=O)O)cc1 | null | null | O=S(=O)(O)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 | 3-(4-Carboxyphenoxy)propionic acid (2.5 g) [prepared according to the procedure of J. Lichtenberger and R. Geyer. Bull. Soc. Chim. Fr., 1963 275] in conc. sulfuric acid (20 ml) was heated to 100° C. for 4 h and then poured onto crushed ice. The resultant precipitate was filtered and dried in vacuo to give the title com... | O=C(O)c1ccc2c(c1)C(=O)CCO2 | null | 70 | null |
1,612,240 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][NH2:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:29][C:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH3:34])[C:31](O)=[O:32].C(N=C=NCCCN(C)C)C.ON... | CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CN)cc3)cc2)CC1 | CC(C)(C(=O)O)c1ccccc1 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | 1-[4′-(4-Aminomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.038 g, 0.1 mmol), α,α-dimethylphenylacetic acid (0.020 g, 0.12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (0.023 g, 0.12 mmol), 1-hydroxybenzotriazole (HOBt) (0.016 g, 0.12 mmol), and triethylamine (0.... | CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CNC(=O)C(C)(C)c4ccccc4)cc3)cc2)CC1 | null | null | null |
1,048,403 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:15])([CH3:14])[C:9]([O:11]CC)=[O:10].[OH-].[K+]>CCO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:15])([CH3:14])[C:9]([OH:11])=[O:10] | CCOC(=O)C(C)(C)c1ccccc1Cl | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A solution of ethyl 2-(2-chlorophenyl)-2-methylpropanoate (3.48 g, 15.4 mmol) and KOH (8.61 g, 154 mmol) in EtOH/water (1:1, 200 mL) was heated at 150° C. in a sealed vessel for 2 hours. The solution was concentrated in vacuo, suspended in diethyl ether (200 mL), and extracted with 1N NaOH(aq) (3×100 mL). The aqueous s... | CC(C)(C(=O)O)c1ccccc1Cl | null | 84.3 | null |
178,568 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | [CH:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:13])=[N-]>CCOCC>[CH:1]1([CH2:7][C:8]([O:10][CH3:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | O=C(O)CC1CCCCC1 | C=[N+]=[N-] | 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 | 0 | null | To an ice-cooled and stirred solution of cyclohexylacetic acid (9.34 g, 0.066 mol) in 30 ml of ether was slowly added an excess solution of diazomethane in ether. After concentration of ether, the residue was distilled under reduced pressure to give a colorless transparent liquid of methyl cyclohexylacetate (7.45 g, 0.... | COC(=O)CC1CCCCC1 | null | 72.4 | null |
522,026 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:18]([N:21]1[C:25](=[O:26])[CH:24]=[CH:23][C:22]1=[O:27])(=[O:20])[NH2:19].O>O1CCOCC1.[Cl-].[Zn+2].[Cl-]>[C:25]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]... | CCCCCCCCCCCCCCCCO | NC(=O)N1C(=O)C=CC1=O | null | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 24 | A mixture of 49 g of hexadecanol (0.202 moles), 28 g of N-carbamylmaleimide (0.2 moles) and 270 mg of zinc chloride (0.002 moles) in 300 mL of p-dioxane was heated to reflux. After 24 hours, the mixture was cooled to room temperature and 200 mL of H2O was added. The resulting solid was filtered, washed with additional ... | CCCCCCCCCCCCCCCCOC(=O)/C=C\C(=O)NC(N)=O | null | 98 | null |
1,464,300 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4](=[O:35])[N:5]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[CH:6]2[CH2:12][CH2:13][C:14]([NH:16][C:17]1C=CC(C(F)(F)F)=C[N:18]=1)=[O:15].NC1[S:38][CH:39]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])N=1>>[CH2:45]([O:44][C:42]([C:40]1[N:18]=[C:17]... | CCOC(=O)c1csc(N)n1 | O=C(CCC1c2c(F)ccc(F)c2C(=O)N1Cc1ccc(F)cc1)Nc1ccc(C(F)(F)F)cn1 | 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 product from Example 18, Part A (100 mg, 0.29 mmol) and ethyl 2-amino-1,3-thiazole-4-carboxylate were converted to the title compound in a manner analogous to the method described in Example 7, Part E without crystallization (80 mg, 55%). 1H (300 MHz, CDCl3) δ 10.31 (s, 1H), 7.77 (s, 1H), 7.28 (m, 2H), 7.12 (m, 1H)... | CCOC(=O)c1csc(NC(=O)CCC2c3c(F)ccc(F)c3C(=O)N2Cc2ccc(F)cc2)n1 | null | null | null |
1,032,812 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH3:1][C:2]1([CH3:15])[CH2:6][N:5](CC2C=CC=CC=2)[CH2:4][C@@H:3]1[OH:14].[ClH:16]>CO.[Pd]>[ClH:16].[CH3:1][C:2]1([CH3:15])[CH2:6][NH:5][CH2:4][C@@H:3]1[OH:14] | CC1(C)CN(Cc2ccccc2)C[C@@H]1O | null | null | [Pd] | Cl | 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 | 48 | To a solution of (3R)-4,4-dimethyl-1-(phenylmethyl)-3-pyrrolidinol (J. Med. Chem. 1992, 35, 4205-4213) (1.8634 g, 9.076 mmol) in MeOH (45 mL) was added 1 N aq. HCl (9.1 mL, 9.1 mmol) and 10% Pd/C (50% water, 375 mg). The mixture was hydrogenated under balloon pressure for 2 days, and was then filtered. The solution was... | CC1(C)CNC[C@@H]1O | null | 91.9 | null |
1,439,653 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:10]=1)#[N:2] | CCOC(=O)c1cnc2ccc(CCC#N)cn12 | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 50 | null | A stirring mixture of ethyl 6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-carboxylate (74) (100 mg, 0.411 mmol) and 2N LiOH (0.2 mL) in THF:MeOH (4:1, 3 mL) was heated at 50° C. for 45 minutes. The reaction was cooled to room temperature and the pH was adjusted between 3-5 with 10% citric acid. The solvent was partially red... | N#CCCc1ccc2ncc(C(=O)O)n2c1 | null | null | null |
369,824 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:16][CH2:17][CH:18]([OH:20])[CH3:19]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:16]([CH2:17][CH:18]([OH:20])[CH3:19])[C:5]=32)=[CH:10][CH:9]=1 | CC(O)CN | O=CCC1Cc2ccc(Cl)cc2C1=O | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 0.75 | A solution of 2.08 g of (RS)-2-(2-oxoethyl)-6-chloro-1-indanone and 80 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 3.0 g of (RS)-1-amino-2-propanol in 20 ml of anhydrous toluene was added dropwise to the boiling solution over a period of 5 minutes. Subsequen... | CC(O)Cn1ccc2c1-c1cc(Cl)ccc1C2 | null | 61.5 | null |
1,587,222 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CON(C)[C:16]([C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=1)=[O:17]>>[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[C:8]([C:16]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5] | CON(C)C(=O)c1cnccn1 | Cc1c(F)ccc(C(=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 | Starting materials: 2,4-difluoro-3-methylbenzoic acid (Intermediate 46) and N-methoxy-N-methylpyrazine-2-carboxamide. | Cc1c(F)c(C(=O)O)cc(C(=O)c2cnccn2)c1F | null | null | null |
1,377,966 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]#[N:17])[CH2:11][C:10]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1.[OH:18]O.[NH4+].[OH-]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]([NH2:17])=[O:18])[CH2:9][C:10]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:11]2)=[CH:4][CH:3]=1 | OO | N#CC1(c2ccc(Br)cc2)CC2(C1)OCCO2 | null | [NH4+] | [OH-] | null | 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 | 25 | 16 | To a mixture of Compound [XXXIII] (13.0 g, 44.2 mmol, 1.0 eq.) in MeOH (520 mL) was added H2O2 (13.7 mL, 33% in water, 133 mmol, 3.00 eq.), and NH4OH (52 mL). The resulting mixture was stirred for 16 hours at room temperature, then diluted with additional water and extracted with ethyl acetate (×3). The combined organi... | NC(=O)C1(c2ccc(Br)cc2)CC2(C1)OCCO2 | null | null | null |
1,722,220 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15](Cl)(=[O:17])[CH3:16]>C(OCC)(=O)C.O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]([CH3:16])=[O:17])=[CH:3][CH:4]=1 | CC(=O)Cl | Cc1ccc(N)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | O | null | null | null | null | null | null | null | null | null | null | 2 | 100 g (933.3 mmol) of p-toluidine and 154.8 g (1.120 mmol) of potassium carbonate were dissolved in a mixed solvent of 1,000 ml of ethyl acetate and 500 ml of water. Thereinto was dropped 87.9 g (1.120 mmol) of acetyl chloride with ice-cooling, followed by stirring for 2 hours. Extraction with ethyl acetate was carried... | CC(=O)Nc1ccc(C)cc1 | null | 77,801.2 | null |
905,385 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13](O)[CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.O=S(Cl)[Cl:18]>CN(C=O)C>[Cl:18][CH:13]([C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)[CH3:14] | CC(O)c1noc(-c2cccc(Cl)c2)n1 | O=S(Cl)Cl | null | null | null | 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 | 70 | null | 5 drops of DMF was added to 1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol (12.3 g, 54.9 mmol) in SOCl2 (150 mL) and the reaction was heated at 70° C. for 5 h. The excess SOCl2 was evaporated and the residue was purified by column chromatography (Hep to Hep-EA 5:1) to give 12.4 g (93%) of the title compound. 1H NMR... | CC(Cl)c1noc(-c2cccc(Cl)c2)n1 | null | 93 | null |
702,536 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH3:13][CH:14]([CH3:18])[CH2:15][CH2:16][OH:17]>>[CH3:13][CH:14]([CH3:18])[CH2:15][CH2:16][O:17][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1 | CC(C)CCO | O=C(O)c1ccc(Cl)nc1 | null | [H-] | [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 | null | null | 6-(3-Methylbutoxy)nicotinic acid was prepared from 6-chloronicotinic acid (0.50 g), 3-methyl-1-butanol (0.36 ml) and sodium hydride (60%, 0.32 g) according to the method described in Example 54 to give the product as a white solid (0.25 g, 38%): δH (400 MHz, DMSO-d6) 12.97 (1H, m), 8.71 (1H, d, J 2.5 Hz), 8.12 (1H, dd,... | CC(C)CCOc1ccc(C(=O)O)cn1 | null | null | null |
284,387 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=2[C:17](O)=[O:18])=[CH:10][CH:9]=1>C(OCC)C.C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=2[CH2:17][OH:18])=[CH:12][CH:13]=1 | O=C(O)c1c(F)cccc1Sc1ccc(F)cc1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 8 | LiAlH4 (0.77 g, 20.4 mmol) is suspended in 30 ml of dry diethyl ether with cooling in an ice bath. 2-(4--fluorophenylthio)-6-fluorobenzoic acid (4.53 g, 17.0 mmol) in 6 ml of diethyl ether and 6 ml of THF is then added and the reaction mixture stirred at room temperature overnight. The reaction mixture is quenched sequ... | OCc1c(F)cccc1Sc1ccc(F)cc1 | null | null | null |
724,964 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22]O)([CH3:16])([CH3:15])[CH3:14].N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:13]([O:17][C:18]([NH:19][CH2:20][CH2:21][CH2:22][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:... | Oc1cccc2c(Cl)nccc12 | CC(C)(C)OC(=O)NCCCO | null | CCCCP(CCCC)CCCC | CN(C)C(=O)N=NC(=O)N(C)C | 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 | 24 | A suspension of 1-chloro-5-hydroxyisoquinoline (539 mg, synthesized according to the method described in a reference (Georgian, V. et al., J. Org. Chem., 27, 4571 (1962))), (3-hydroxypropyl)carbamic acid tert-butyl ester (1.58 g, Tokyo Kasei Kogyo) and 1,1′-azobis(N,N-dimethylformamide) (1.55 g) in tetrahydrofuran (8 m... | CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12 | null | null | null |
985,495 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][CH:35]([C:37]([O:39]CC)=[O:38])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.[OH-].[Na+].O>C1COCC1>[Br:1... | CCOC(=O)C(C)COc1ccc(Br)cc1C1CC(=O)NC(c2cc(Cl)ccc2C)C12C(=O)Nc1cc(Cl)ccc12 | null | null | [Na+] | [OH-] | 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 | 80 | null | A mixture of racemic (2′S,3S,4′R)-4′-[5-bromo-2-(2-ethoxycarbonyl-2-methyl-ethoxy)-phenyl]-6-chloro-2′-(5-chloro-2-methyl phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (200 mg, 0.3 mmol), NaOH (40 mg, 1 mmol), H2O (5 mL) and THF (5 mL) was heated at 80° C. for 2 h. Then THF was removed in vacuum. The water sol... | Cc1ccc(Cl)cc1C1NC(=O)CC(c2cc(Br)ccc2OCC(C)C(=O)O)C12C(=O)Nc1cc(Cl)ccc12 | null | 52.7 | null |
359,949 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH2:19])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:20]1[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[N:21]1>>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:25]([C:22]3[CH:23]=[CH... | NC/C=C\COc1cc(CN2CCCCC2)ccn1 | O=C(O)c1cc[nH]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 | Following a procedure similar to that described in Example 13, but using 4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenylamine and 3-pyrazolecarboxylic acid as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained as an oil in a 57% yield. | O=C(NC/C=C\COc1cc(CN2CCCCC2)ccn1)c1cc[nH]n1 | null | 57 | null |
303,796 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | C([C:3]([C:17]([O:19][CH3:20])=[O:18])=[C:4]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH:5]=[CH:6][N:7](C)[CH3:8])#N.[BrH:21]>C(O)(=O)C>[CH3:20][O:19][C:17](=[O:18])[C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:5][CH:6]=[N:7][C:8]=1[Br:21] | COC(=O)C(C#N)=C(C=CN(C)C)c1ccc(Cl)cc1 | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 25 | null | 80.0 g (0.28 mol) of 1-cyano-1-methoxycarbonyl-4-(N,N-dimethylamino)-2-(4-chlorophenyl)-1,3-butadiene was weighed, and 100 ml of acetic acid was added thereto and an acetic acid solution of 25% HBr was then gradually added dropwise thereto at room temperature under stirring. After the dropwise addition, the resultant m... | COC(=O)c1c(-c2ccc(Cl)cc2)ccnc1Br | null | 83.5 | null |
1,265,982 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[C:3]=1[N+:9]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:9][C:3]1[C:4]([OH:8])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1] | O=[N+]([O-])c1c(Cl)ccnc1O | null | null | Cl[Sn](Cl)(Cl)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 | 2 | 4-chloro-3-nitro-pyridin-2-ol (1.69 g, 9.72 mmol) and tin tetrachloride dihydrate (SnCl2.2H2O) (10.97 g, 48.62 mmol) was dissolved in ethanol (32 ml), heated to 70□ and stirred for 2 hours. The reaction mixture was cooled to room temperature and the ethanol was evaporated under reduced pressure. The residue was neutral... | Nc1c(Cl)ccnc1O | null | 46.3 | null |
469,674 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[O:29]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][NH:26][C:10]([CH:7]1[CH2:6][CH2:5]... | NCC(=O)c1ccccc1 | CC(=O)N1CCC(C(=O)O)CC1 | null | Cl | O=C(n1ccnc1)n1ccnc1 | 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 | 23 | 1.5 | A suspension of 1-acetyl-4-piperidine carboxylic acid (93 g, 542 mmol) in CH2Cl2 (700 mL) is treated portionwise at 23° C. with carbonyldiimidazole (80 g, 542 mmol). The solution is allowed to stir at 23° C. under N2 for 1.5 h, then treated with 2-aminoacetophenone hydrochloride (93 g, 542 mmol) and diisopropylethylami... | CC(=O)N1CCC(C(=O)NCC(=O)c2ccccc2)CC1 | null | 78.1 | null |
1,582,971 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:17])=[CH:16][C:3]=12.CC(C)([O-])C.[Na+].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CN(C=O)C>[Br:17][C:15]1[S:14][C:4]2=[N:5][C:6]([CH3:13])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9... | O=S(=O)(Cl)c1ccccc1 | CCOC(=O)c1c(C)nc2sc(Br)cc2c1N | null | CC(C)(C)[O-] | [Na+] | 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 | 25 | 0.5 | To a stirring mixture of ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 66) (5.84 g, 18.53 mmol) in THF (110 mL) and DMF (55 mL) was added sodium tert-butoxide (4.45 g, 46.3 mmol) and benzenesulfonyl chloride (4.75 mL, 37.1 mmol). The resulting mixture was stirred at RT for 30 min. The r... | CCOC(=O)c1c(C)nc2sc(Br)cc2c1NS(=O)(=O)c1ccccc1 | null | 74.3 | null |
1,171,409 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([I:15])[N:12]=[C:11]1[CH3:16])(C)(C)C.[ClH:18].O1CCOCC1>C(Cl)Cl>[I:15][C:13]1[N:12]=[C:11]([CH3:16])[N:10]([CH2:9][CH2:8][NH2:7])[CH:14]=1.[ClH:18] | Cc1nc(I)cn1CCNC(=O)OC(C)(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1COCCO1 | null | null | null | null | null | null | null | null | null | 0 | 0.25 | To an ice-cooled solution of [2-(4-iodo-2-methyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (2.800 g; 7.973 mmol) in DCM (45 ml) was added slowly 4N HCl in dioxane (28.25 ml; 113.000 mmol). The resulting suspension was stirred at 0° C. for 15 min., then at rt for 1 h. The volatiles were removed under reduced ... | Cc1nc(I)cn1CCN | null | null | null |
1,757,038 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:12][C:13]1[C:33]2[O:32][C@:19]3([C@H:28]([CH3:29])[CH2:27][C:26]4[N:25]=[C:24]([CH3:30])[CH:23]=[CH:22][C:21]=4[C:20]3=[O:31])[C:18](=[O:34])[C:17]=2[C:16]([O:35][CH3:36])=[CH:15][C:14]=1[O:37][CH3:38]>ClCCl>[Cl:12][C:13]1[C:33]2[O:32][C@:19]3([C@H:28]([CH3:29])[CH2:27][C:26]4[N:25]=[C... | O=C(OO)c1cccc(Cl)c1 | COc1cc(OC)c2c(c1Cl)O[C@@]1(C(=O)c3ccc(C)nc3C[C@H]1C)C2=O | null | null | 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 | null | 16 | In a 250 mL round-bottomed flask 1.3 g (7.7 mmol, 2 eq.) of mCPBA was added to a solution of (2S,7′R)-7-chloro-4,6-dimethoxy-2′,7′-dimethyl-7′,8′-dihydro-3H,5′H-spiro[benzofuran-2,6′-quinoline]-3,5′-dione (1.5 g, 3.9 mmol, 1.0 eq) in 45 mL of dichloromethane. The mixture was left under agitation at ambient temperature ... | CCc1ccc2c(n1)C[C@@H](C)[C@]1(Oc3c(Cl)c(OC)cc(OC)c3C1=O)C2=O | null | 102.1 | null |
435,541 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH:10]=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[C:6]([CH3:19])[C:5]=1[N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21]>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][... | COC(=O)c1cc(C=CC(=O)OC(C)(C)C)cc(C)c1N(C)S(=O)(=O)c1ccc(OC)cc1 | null | null | [Pd] | null | 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 | 2 | A mixture of 340 mg (0.71 mmol) of the product of Example 203 and 35 mg of 10% palladium on carbon in 15 ml of ethanol was hydrogenated on a Parr shaker for 2 hr. The resulting mixture was filtered through Celite and Magnesol to provide 325 mg (95%) of the desired product as a colorless gum. Electrospray Mass Spec 478(... | COC(=O)c1cc(CCC(=O)OC(C)(C)C)cc(C)c1N(C)S(=O)(=O)c1ccc(OC)cc1 | null | 95.8 | null |
332,097 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([NH:8][NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7].[CH3:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:22](Cl)=[O:23].[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([NH:8][N:9]([C:22](=... | COc1cccc(C(=O)NNC(C)(C)C)c1C | Cc1cc(C)cc(C(=O)Cl)c1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | null | null | To a stirred solution of N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine (506 g, 2.14 mole) in methylene chloride (1.5 L) at 5° C. were simultaneously added solutions of 3,5-dimethylbenzoyl chloride (360 g, 2.14 moles) in methylene chloride (500 mL) and sodium hydroxide (50% aqueous, 171.2 g, 2.14 moles) diluted w... | COc1cccc(C(=O)NN(C(=O)c2cc(C)cc(C)c2)C(C)(C)C)c1C | null | 84.1 | null |
509,195 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1I.C(N(CC)CC)C.[CH:29]#[C:30][CH3:31]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[... | C#CC | N#Cc1nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c(N)c1I | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | -78 | 48 | To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-iodopyrazole (0.904 g, the compound of Example A1) in dimethylformamide(2 ml) and triethylamine (10 ml) contained in a stainless steel bomb was added cuprous iodide (60 mg) and bis(triphenylphosphine)palladium(II) chloride (120 mg). The ... | CC#Cc1c(C#N)nn(-c2c(Cl)cc(C(F)(F)F)cc2Cl)c1N | null | null | null |
486,634 | ord_dataset-7b02d32cc502407f94aea8e5caf405a2 | null | 2000-01-01T00:12:00 | true | [C:1]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])C.CC(C)=O.N1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH2:15]([C:8]1[CH:7]=[CH:6][C:5](=[C:1]([CH3:3])[CH3:4])[CH:9]=1)[CH2:16][CH2:17][CH3:18] | CC(C)(C)C1=CC=CC1 | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CO | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A mixture of t-butylcyclopentadiene (15 g, 123 mmol), acetone (9.0 mL, 135.2 mmol), pyrrolidine (11.7 mL, 135.3 mmol) and methanol (100 mL) was stirred at 0° C., for 30 minutes, and then at room temperature overnight. The reaction mixture was quenched with acetic acid (7.38 g) and with water (100 mL) at 0° C. The mixtu... | CCCCC1=CC(=C(C)C)C=C1 | null | 91.4 | null |
1,617,789 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [OH-].[Na+].Cl[C:4]([O:6][CH2:7][C:8]([Cl:11])([Cl:10])[Cl:9])=[O:5].Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18]>>[Cl:9][C:8]([Cl:11])([Cl:10])[CH2:7][O:6][C:4]([NH:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])=[O:5] | O=C(Cl)OCC(Cl)(Cl)Cl | Nc1cccc(C(=O)O)c1 | null | Cl | [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 | To an aqueous solution (200 ml) of 8.22 g of m-aminobenzoic acid and 4.8 g of sodium hydroxide was dropwise added 25.0 g of 2,2,2-trichloroethyl chloroformate at room temperature. During the dropwise addition, the reaction solution was controlled to pH 10 or more by appropriately adding a 1N sodium hydroxide aqueous so... | O=C(Nc1cccc(C(=O)O)c1)OCC(Cl)(Cl)Cl | null | 86.5 | null |
1,746,331 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].[CH2:19]([NH2:25])[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][O:24]1)=[CH:13][CH:12]=[CH:11][C:10... | CCOC(=O)c1cnc2c(OC)cccc2c1Cl | NCc1ccco1 | 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-Chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (300 mg, 1.13 mmol) was treated with furfurylamine following general procedure B to afford 8-methoxy-4-[(tetrahydro-furan-2-ylmethyl)-amino]-quinoline-3-carboxylic acid ethyl ester (280 mg). Thus obtained amino-ester was hydrolyzed to the corresponding acid in ... | CCOC(=O)c1cnc2c(OC)cccc2c1NCC1CCCO1 | null | null | null |
1,495,628 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [NH2:1][N:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].[CH3:19][N:20]([CH3:31])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1>>[CH3:31][N:20]([CH3:19])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:1][N:2]2[N:11]=[C:10](... | Nn1nc(N2CCOCC2)c2ccccc2c1=O | CN(C)c1ccc(CC(=O)O)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 product of Example 1B and 2-[4-(dimethylamino)phenyl]acetic acid were treated using a method similar to that described in Example 111 to give the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ 8.30 (dd, J=7.9, 1.0, 1H), 8.04 (d, J=7.5, 1H), 8.02-7.96 (m, 1H), 7.94-7.88 (m, 1H), 7.47 (d, J=8.7, 2H), 7.37 (d, J=8.6,... | CN(C)c1ccc(CC(=O)Nn2nc(N3CCOCC3)c3ccccc3c2=O)cc1 | null | null | null |
1,031,967 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.Br[CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19].[H-].[Na+]>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:7]=1 | CC(C)=CCBr | Ic1ccc(Nc2ncccn2)cc1 | null | [H-] | [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 | null | null | In the same manner as in Reference Example 13, N-(4-iodophenyl)pyrimidin-2-amine (150 mg) and 1-bromo-3-methyl-2-butene (90 mg) were reacted in the presence of sodium hydride to obtain N-(4-iodophenyl)-N-(3-methyl-2-butenyl)pyrimidin-2-amine (175 mg). | CC(C)=CCN(c1ccc(I)cc1)c1ncccn1 | null | 94.9 | null |
117,781 | ord_dataset-3708161f4ba04e959b9a7a8d59fd86e1 | null | 1984-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)C.[Pt]=O>[OH:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:9]1([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=... | [H][H] | CCOC(=O)CC1(c2cccc(OC)c2)CCCCC1=O | null | O=[Pt] | null | 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 | null | 200 g of ethyl 1-(m-methoxyphenyl)-2-oxo-cyclohexaneacetate are dissolved in 2000 ml of ethanol, and after treatment with 20 g of platinum oxide, the mixture is reduced with hydrogen at 50° C. and 50 bar. After separation of the catalyst, the solvent is removed by distillation, and there is obtained ethyl 2-hydroxy-1-(... | CCOC(=O)CC1(c2cccc(OC)c2)CCCCC1O | null | null | null |
1,298,591 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | N1C=CN=C1.[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:17])([CH3:16])[CH3:15])[N:9]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:17])([CH3:15])[CH3:16])[N:9]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])... | CC(C)(O)c1cccc(CO)n1 | CC(C)(C)[Si](C)(C)Cl | null | c1c[nH]cn1 | null | 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 | 16 | Imidazole (2.27 g, 33.3 mmol) was added to a stirred solution of 2-hydroxymethyl-6-(1-hydroxy-1-methylethyl)pyridine (5.30 g, 31.7 mmol) and tert-butyldimethylsilylchloride (5.02 g, 33.3 mmol) in DMF (70 mL) and the mixture was stirred for 16 h at room temperature. The mixture was poured onto water, extracted with EtOA... | CC(C)(O)c1cccc(CO[Si](C)(C)C(C)(C)C)n1 | null | 91.8 | null |
1,305,146 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | O1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][C:10](=[O:13])[NH:9]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[NH:9]1[C:8]2([CH2:14][CH2:15][C:5](=[O:4])[CH2:6][CH2:7]2)[CH2:12][CH2:11][C:10]1=[O:13] | O=C1CCC2(CCC3(CC2)OCCO3)N1 | 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 | 25 | 20 | A suspension of 1,4-dioxa-9-aza-dispiro[4.2.4.2]tetradecan-10-one (prepared according to J. Org. Chem. 2004, 69, 2755) (500 mg, 2.4 mmol) in THF (7 mL) was treated with 1M aqueous HCl (7 mL) and the resulting mixture stirred at ambient temperature for 20 hours. The reaction mixture was quenched with 1M aqueous NaOH (7 ... | O=C1CCC2(CC1)CCC(=O)N2 | null | 99.2 | null |
804,583 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH:18]2O[CH:21]=[N:20][C:19]2([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])S(C2C=CC(C)=CC=2)(=O)=O)[N:9]=[N:8]1.C[NH2:51].CO>C1(C... | Cc1ccc(S(=O)(=O)C2(Cc3ccccc3Cl)N=COC2c2nnn(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)c2-c2ccccc2)cc1 | CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | 25 | 19 | Combine 1-(3,5-bis-trifluoromethyl-benzyl)-4-[4-(2-chloro-benzyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazol-5-yl]-5-phenyl-1H-[1,2,3]triazole (0.100 mmol), 2.5 mL of xylene, and 2N solution of methylamine in methanol (0.2 mL, 0.40 mmol) and heat in a sealed pyrex tube to 135° C. After 19 hours, cool to RT. Concentrate ... | FC(F)(F)c1cc(Cn2nnc(-c3nc[nH]c3Cc3ccccc3Cl)c2-c2ccccc2)cc(C(F)(F)F)c1 | null | null | null |
308,974 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:12]1([CH2:18][CH2:19][CH:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22][C:21]2=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([CH2:18][CH2:19][C:20]2([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][N:3]=3)[C:25](=[O:26])[... | O=C1NC(=O)C(CCc2ccccc2)C(=O)N1 | Clc1ncnc2ccccc12 | 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 | 170 | null | A mixture of 3.3 g of 4-chloroquinazoline and 4.65 g of 5-(2-phenylethyl) barbituric acid was heated to 170° C. for two and one-half hours, then cooled to form the 5-(2-phenylethyl)-5-(4-quinazolyl) barbituric acid. This compound was hydrolyzed, without isolation, by adding 40 ml of water and 4.5 g of NaOH to the mixtu... | O=C1NC(=O)C(CCc2ccccc2)(c2ncnc3ccccc23)C(=O)N1 | null | null | null |
235,495 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([C:34](=[O:36])[NH2:35])[N:33]=[C:29]4[N:28]=[C:27]([CH3:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[NH2:39][O:40][CH2:41][C:42]1[NH:43][CH:44]=[... | NOCc1nc(=O)c(O)c[nH]1 | Cc1cc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)C(=O)c4csc(N)n4)[C@H]3SC2)n2nc(C(N)=O)nc2n1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 0.33 | 0.230 g (0.4 mmol) of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido) -3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid was dissolved in 3.5 ml of dimethylacetamide. Within 6 hours 0.11 g (0.7 mmol) of 2-(aminooxy)methyl-5-hydroxy-4(1H)-pyrim... | Cc1cc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)/C(=N\OCc4nc(=O)c(O)c[nH]4)c4csc(N)n4)[C@H]3SC2)n2nc(C(N)=O)nc2n1 | null | null | null |
863,790 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | FC(F)(F)C(O)=O.[CH:8]1([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]([NH:19]C(=O)OC(C)(C)C)[C:13]2=[O:27])[CH2:10][CH2:9]1>ClCCl>[NH2:19][C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][N:12]([CH2:11][CH:8]2[CH2:10][CH2:9]2)[C:13]1=[O:27] | CC(C)(C)OC(=O)N[C@@H]1CCCCN(CC2CC2)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 1 | Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl (3R)-1-(cyclopropylmethyl)-2-oxoazepan-3-ylcarbamate (257 mg, 0.91 mmol) in dichloromethane (10 mL). After 1 h, the mixture was concentrated and azeotroped with dichloromethane (3×) to give the crude amine. | N[C@@H]1CCCCN(CC2CC2)C1=O | null | null | null |
1,248,127 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[C:4](=[O:22])[C:5](C(O)=O)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:8]=1.C1C=CC(P([N:37]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:37][C:5]1[C:4](=[O:22])[C:3]([O:2][CH3:1])=[CH:8][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11... | [N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COc1cn(-c2cccc(C(F)(F)F)c2)nc(C(=O)O)c1=O | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 100 | 3 | A mixture of 5-methoxy-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylic acid (6.00 g, 19.1 mmol), DPPA (6.16 mL, 28.6 mmol) and Et3N (3.99 mL, 28.6 mmol) in toluene (60 mL) was heated to 100° C. for 2 h. To the mixture was added 8 M NaOH aqueous solution (23.8 mL) at 0° C. The mixture was stirred ... | COc1cn(-c2cccc(C(F)(F)F)c2)nc(N)c1=O | null | 65.5 | null |
879,988 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1)=[O:4].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][O:16][C:13](=[O:15])[CH3:14])=[N:7][CH:8]=1 | O=C(CCl)Nc1ccc(Cl)cn1 | CC(=O)[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | 5 | 2-Cloro-N-(5-chloropyridin-2-yl)acetamide (30.68 g) obtained in Reference Example 20(1) is dissolved in N,N-dimethylformamide (500 ml), thereto is added sodium acetate (24.55 g) and the mixture is stirred at 60° C. for 5 hours. The reaction solution is diluted with ethyl acetate, washed successively with water and satu... | CC(=O)OCC(=O)Nc1ccc(Cl)cn1 | null | 89.4 | null |
1,215,714 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[H-].[Na+].Cl[C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[CH3:17][O:16][C:14](=[O:15])[O:10][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[C:7]([F:8])[C:2]=1[F:1] | COC(=O)Cl | Cc1ccc(O)c(F)c1F | 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 | 3 | A solution of 2,3-difluoro-4-methyl phenol (3.3 g, 22.89 mmol) in THF (30 ml) was cooled to 0° C. in an ice bath, and 60% NaH (0.916 g, 22.9 mmol) was added. When the gas evolution ceased, methyl chloroformate (1.76 ml, 22.9 mmol) was added. The ice-bath was removed and the mixture was stirred at room temperature for t... | COC(=O)Oc1ccc(C)c(F)c1F | null | 83.2 | null |
334,725 | ord_dataset-ba1248d90e3e465693710bbc45866f37 | null | 1996-01-01T00:07:00 | true | [F:1][C:2]1[C:3]([CH2:35][OH:36])=[C:4]([F:34])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)C(C)(C)C)=[C:13]([F:24])[CH:12]=3)=[CH:8][C:7](=[O:25])[C:6]=2[C:26]=1[NH:27]C(=O)C(C)(C)C.[C:37](O)(=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].S(=O)(=O)(O)O>>[NH2:27][C:26]1[C:6]2[C:7](=[O:25])[CH:8]=[C:9]([... | CC(C)(C)C(=O)Nc1ccc(-c2cc(=O)c3c(NC(=O)C(C)(C)C)c(F)c(CO)c(F)c3o2)cc1F | CCCCCC(=O)O | null | O=S(=O)(O)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 | Substantially the same manner as that in Example 123 was repeated except that 1.06 g (2.10 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in Example 118 (4), 24 mL of hexanoic acid and 6 mL of concentrated sulfuric acid were used, and the resultin... | CCCCCC(=O)OCc1c(F)c(N)c2c(=O)cc(-c3ccc(N)c(F)c3)oc2c1F | null | 55 | null |
1,629,295 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:39])[CH2:23][O:24][C:25]2[CH:38]=[CH:37][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[NH:32][C:31]3=[O:36])=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1.CS(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([C:22](=[O:39])[CH2:23][O:24][C... | O=C1NC(=O)C(Cc2ccc(OCC(O)c3cccc(Cl)c3)cc2)S1 | null | null | O=C([O-])O | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 0.25 | To a stirring solution of phosphorus pentoxide (0.38 g, 1.30 mmol) in DCM (8 mL) at 0° C. was added a solution of 5-{4-[2-(3-chlorophenyl)-2-hydroxyethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.25 g, 0.66 mmol) in DCM (8 mL) followed by dimethyl sulfoxide (0.23 mL, 3.30 mL). After stirring for 15 minutes N,N-diiisopropy... | O=C1NC(=O)C(Cc2ccc(OCC(=O)c3cccc(Cl)c3)cc2)S1 | null | 47.2 | null |
1,375,568 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:19]1[C:20]2[CH:27]=[CH:26][NH:25][C:21]=2[N:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6]([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][N:14]([C:19]3[C:20]4[CH:27]=[CH:26][N... | CC(C)(C)OC(=O)N1CCCC12CCCNC2 | Clc1ncnc2[nH]ccc12 | null | O=C([O-])[O-] | [K+] | 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 | 1.5 | 1,7-Diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester (51 mg) was mixed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (36 mg), potassium carbonate (59 mg) and water (1 ml), and the mixture was stirred for 1.5 hours with refluxing. The mixture was cooled to room temperature, and thereto was added water. The mixture w... | CC(C)(C)OC(=O)N1CCCC12CCCN(c1ncnc3[nH]ccc13)C2 | null | 79.1 | null |
752,989 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [NH2:1][C:2]1[C:3]([NH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:27](OCC)(=[O:33])[C:28](OCC)=[O:29]>C(OCCO)C>[CH:22]1([N:21]2[C:3]3[N:4]=[C:5]([NH:8][C:9]4[CH:14]=[CH:13][C:12]([N:15]5[CH... | CCOC(=O)C(=O)OCC | Nc1cnc(Nc2ccc(N3CCOCC3)cc2)nc1NC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 0.354 g (1 mmol) of 5-amino-4-(cyclopentylamino)-2-[[4-(morpholin-4-yl)phenyl]amino]pyrimidine and 5 mL (32 mmol) of diethyl oxalate in 20 mL of 2-ethoxyethanol is heated under reflux for 3 hours and then cooled to give 0.20 g (49%) of the title compound (Compound 23): mp (EtOH) 283–286° C. 1H NMR [(CD3)2S... | O=c1[nH]c2cnc(Nc3ccc(N4CCOCC4)cc3)nc2n(C2CCCC2)c1=O | null | 49 | null |
1,691,228 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [CH3:1][C:2]1[C:7]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>C(O)C.[H][H]>[CH3:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1 | [H][H] | Cc1ncccc1C1=CCN(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 | CCO | null | null | null | null | null | null | null | null | null | null | null | null | tert-Butyl 4-(2-methyl-3-pyridyl)-3,6-dihydro-2H-pyridine-1-carboxylate (209 mg, 0.76 mmol) was dissolved in ethanol (42 ml) and hydrogenated in a H-cube hydrogen generator with a flow of 1 ml/min and at a temperature of 70° C. The mixture was evaporated under reduced pressure, the residue was purified by preparative H... | Cc1ncccc1C1CCN(C(=O)OC(C)(C)C)CC1 | null | 47.4 | null |
606,610 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:28]1[CH:29]=[CH:30][C:31]2[N:32]([C:34](=[O:38])[N:35]([CH3:37])[N:36]=2)[N:33]=1>CN(C)C=O>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:... | Cn1nc2ccc(Cl)nn2c1=O | OCCCN1CCC(OC(c2ccccc2)c2ccccc2)CC1 | 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 | 1 | 0.52 g of 4-(diphenylmethoxy)-1-piperidinepropanol was dissolved in 3 ml of N,N-dimethylformamide; 0.0704 g of 60% oily sodium hydride was added, followed by stirring at room temperature for 1 hour. 0.325 g of 6-chloro-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one was added, followed by stirring at room temperature... | Cn1nc2ccc(OCCCN3CCC(OC(c4ccccc4)c4ccccc4)CC3)nn2c1=O | null | 66.3 | null |
1,515,117 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([C:3]1[CH:4]=[C:5]2[C:11]([CH:12]([OH:28])[C:13]3[C:14]([F:27])=[C:15]([NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1)#[N:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([C:12]([C:13]3[C:14]([F:27])=... | CCCS(=O)(=O)Nc1ccc(F)c(C(O)c2c[nH]c3ncc(C#N)cc23)c1F | null | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | 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 propane-1-sulfonic acid {3-[(5-cyano-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-amide (14, 313 mg, 0.770 mmol) dissolved in 5 mL of tetrahydrofuran, Dess-Martin periodinane (327 mg, 0.770 mmol) was added as a solid. The reaction was stirred at room temperature for 1 hour, then quenched with ... | CCCS(=O)(=O)Nc1ccc(F)c(C(=O)c2c[nH]c3ncc(C#N)cc23)c1F | null | 57.5 | null |
1,195,526 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].B.C1COCC1>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH2:13][NH2:14])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1)([O-:3])=[O:2] | N#CC1(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | B | 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 | null | The mixture of 1-(4-nitro-phenyl)-cyclopropanecarbonitrile (3.0 g, 15.9 mmol) and borane THF complex (1.0 M solution in THF, 32 ml, 32 mmol) in 50 ml of anhydrous THF was heated at reflux overnight. The mixture was cooled to RT, quenched with 2.5 ml of 50% AcOH aqueous solution, then partitioned between EtOAc and NaHCO... | NCC1(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | null |
734,696 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [C:1]([CH2:4][S:5][C:6]1[N:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=[C:8]([CH2:20][CH2:21][CH3:22])[C:7]=1[C:23]#[N:24])(=[O:3])[NH2:2].Cl.Cl.Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([NH:34][CH2:35][CH:36]([OH:45])[CH2:37][O:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[CH2:30][CH2:29]1.C[O-].[Na+].CO>CN(C=O)C>[NH2:24][C:23]... | OC(CNC1CCNCC1)COc1ccncc1 | CCCc1cc(OS(=O)(=O)C(F)(F)F)nc(SCC(N)=O)c1C#N | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CO | null | null | null | null | null | null | null | null | null | 70 | 2 | To a sealed tube was added trifluoro-methanesulfonic acid 6-carbamoylmethylsulfanyl-5-cyano-4-propyl-pyridin-2-yl ester (66.7 mg, 0.174 mmol) in 4 mL of dry DMF, followed by the addition of 1-(piperidin-4-ylamino)-3-(pyridin-4-yloxy)-propan-2-ol trihydrochloride salt (69 mg, 0.191 mmol) and N-N-diisopropylethylamine (1... | CCCc1cc(N2CCC(NCC(O)COc3ccncc3)CC2)nc2sc(C(N)=O)c(N)c12 | null | 28.5 | null |
1,717,224 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[C:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:3]=1 | [H][H] | Cc1ccnc(C#CCNC(=O)OC(C)(C)C)c1 | null | [Pd] | null | 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 | null | The residue of step A was dissolved in absolute ethanol (50 ml). The solution was flushed with argon, and a slurry of Pd/C (9.346 g, 0.325 mmol) in absolute ethanol (20 ml) was added. The resulting suspension was stirred in an athmosphere of hydrogen overnight. The reaction mixture was filtered and the filtrate was eva... | Cc1ccnc(CCCNC(=O)OC(C)(C)C)c1 | null | null | null |
1,142,470 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)/[C:9]1=[O:26])=O)(C)(C)C.[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([O:43][CH:44]2[CH2:53][CH2:52][C:47]3([O:51][CH2:50][CH2:49][O:48]3)[CH2:46][CH2:45]2)=[C:32]([CH:34]=[N:35][C:36]([O:38... | CC(C)(C)OC(=O)N1C(=O)/C(=C\c2cccc(Cl)c2)c2ccc(Cl)cc21 | C=C(N=Cc1cc(Cl)ccc1OC1CCC2(CC1)OCCO2)O[Si](C)(C)C | 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 | null | null | In a manner similar to the method described in example 1e, E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester prepared in example 1b (0.4 g, 1 mmol) was reacted 1-[5-chloro-2-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene (1.5 g, 5 mmol) i... | O=C1CC(c2cccc(Cl)c2)C2(C(=O)Nc3cc(Cl)ccc32)C(c2cc(Cl)ccc2OC2CCC3(CC2)OCCO3)N1 | null | null | null |
33,672 | ord_dataset-2e96d163c3f64eb5b470e1ea1a41922a | null | 1977-01-01T00:12:00 | true | Cl[C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:11][CH3:12])[C:6]=2[N:5]=[C:4]2[C:13](=[O:22])[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[CH2:16][CH2:17][C:3]=12.[Na].[CH2:24]([OH:26])[CH3:25]>>[CH2:24]([O:26][C:2]1[C:7]2[CH:8]=[N:9][N:10]([CH2:11][CH3:12])[C:6]=2[N:5]=[C:4]2[C:13](=[O:22])[C:14]3[CH:21]=[CH:20][CH:19]=[CH:18]... | CCn1ncc2c(Cl)c3c(nc21)C(=O)c1ccccc1CC3 | CCO | null | [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 | null | null | null | 6.2 g. of 4-chloro-1-ethyl-5,6-dihydrobenzo[5,6]-cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-one (0.02 mol.) are added to a solution of 0.5 g. of sodium (0.022 mol.) in 150 ml. of absolute ethanol. The mixture is heated at 120° (bath temperature) in an autoclave for four hours. After cooling, the crystallized 4-etho... | CCOc1c2c(nc3c1cnn3CC)C(=O)c1ccccc1CC2 | null | null | null |
639,833 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | C[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[CH:2][S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12] | O=[N+]([O-])O | Cc1nc2ccccc2s1 | null | O=S(=O)(O)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 | 25 | null | See FIG. 3A. Nitration of 2-methylbenzothiazole was performed following the method of Mizuno, J. Pharm. Soc. Japan, 72, 745 (1952). A mixture of fuming nitric acid (1.6 mL) and concentrated sulfuric acid (1.2 mL) was added to an ice-cooled solution of 2-methylbenzothiazole (2 g) in sulfuric acid (8 mL). The solution wa... | O=[N+]([O-])c1ccc2ncsc2c1 | null | null | null |
386,631 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | CS(C)=O.[F:5][C:6]1[C:11]2[N:12]=[C:13]([S:15][CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[S:14][C:10]=2[C:9]([F:26])=[CH:8][C:7]=1[F:27].Br[CH2:29][C:30]([OH:32])=[O:31].C(=O)([O-])[O-].[K+].[K+]>O>[F:5][C:6]1[C:11]2[N:12]=[C:13]([S:15][CH2:16][C:17]([N:19]([C:20]3[CH:25]=[CH:24][CH:23... | O=C(O)CBr | O=C(CSc1nc2c(F)c(F)cc(F)c2s1)Nc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 5 | To DMSO (5 ml) was added 2-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamide (354 mg, 1 mmol), bromoacetic acid (278 mg, 2 mmol) and potassium carbonate (414 mg, 3 mmol) and the mixture was stirred at room temperature for 5 hours under a nitrogen stream. The resultant reaction mixture was diluted with water and ... | O=C(O)CN(C(=O)CSc1nc2c(F)c(F)cc(F)c2s1)c1ccccc1 | null | 19.4 | null |
284,344 | ord_dataset-d63ab258f4634f87bdebbaff0a341c28 | null | 1994-01-01T00:02:00 | true | [N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:2]=[O:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17]>O1CCCC1>[CH2:8]([O:7][C:5]([CH2:4][NH:1][C:2]([O:10][C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][C:23]([C:2... | CCOC(=O)CN=C=O | O=C(C=Cc1cc(O)c(O)c([N+](=O)[O-])c1)c1ccccc1 | 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 | 20 | 72 | 1.5 g of ethyl isocyanatoacetate was added to a solution containing 0.54 g of the product obtained in Example 8 in 10 ml of tetrahydrofuran and the solution was stirred for 3 days at 20° C. The solvent was evaporated in reduced pressure and the raw product was purified in a silica gel column using toluene-dioxane-aceti... | CCOC(=O)CNC(=O)Oc1cc(C=CC(=O)c2ccccc2)cc([N+](=O)[O-])c1O | null | 16.6 | null |
1,361,916 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | COC1C=C(OC)C=CC=1C[NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@H:23]4[C@H:19]([O:20]C(C)(C)[O:22]4)[C@@H:18]([CH2:26][N:27]([CH3:47])[CH:28]4[CH2:31][CH:30]([CH2:32][CH2:33][C:34]5[NH:38][C:37]6[CH:39]=[CH:40][C:41]([CH:43]7[CH2:46][O:45][CH2:44]7)=[CH:42][C:36]=6[N:35]=5)[CH2:29]4)[CH2:17]3)[C:9]=2[N:10]=[CH:11... | COc1ccc(CNc2ncnc3c2ccn3[C@@H]2C[C@H](CN(C)C3CC(CCc4nc5cc(C6COC6)ccc5[nH]4)C3)[C@H]3OC(C)(C)O[C@H]32)c(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 0 | 2 | N-(2,4-dimethoxybenzyl)-7-((3aS,4R,6R,6aR)-2,2-dimethyl-6-((methyl(3-(2-(5-(oxetan-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)cyclobutyl)amino)methyl)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (115 mg, 0.159 mmol) was dissolved in a mixture of Trifluoroacetic Acid (4.00 ml, 51.9 mmol) an... | CN(C[C@H]1C[C@@H](n2ccc3c(N)ncnc32)[C@H](O)[C@@H]1O)C1CC(CCc2nc3cc(C4COC4)ccc3[nH]2)C1 | null | 43.8 | null |
32,514 | ord_dataset-8f61d01cf5b34e85a3ccc89f8901797b | null | 1977-01-01T00:11:00 | true | [CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O[CH2:28][CH:29]([OH:31])[CH3:30].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:28]... | CCCCCCCCCCCCCCCCNc1ccc(C(=O)O)cc1 | CC(O)CO | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOCC | null | null | null | null | null | null | null | null | null | null | 8 | A solution of 7.2 g. of 4-n-hexadecylaminobenzoic acid, 15.2 g. of 1,2-dihydroxypropane, and 3.9 ml. of boron trifluoride etherate are stirred together, under nitrogen, at 115° C. for 19 hours. The solution is cooled, diluted with methylene chloride, and placed in a freezer overnight. The solid is collected, washed wit... | CCCCCCCCCCCCCCCCNc1ccc(C(=O)OCC(C)O)cc1 | null | null | null |
152,268 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([C:9]1[CH:27]=[CH:26][C:12]([NH:13][C:14](=[O:25])[C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[CH2:16][S:17][CH2:18][CH3:19])=[CH:11][C:10]=1[C:28]([F:31])([F:30])[F:29])#[N:8]>O.CO>[C:7]([C:9]1[CH:27]=[CH:26][C:12]([NH:13][C:14](=[O:25])[C:15]([OH:24])([C:20]([F:21])([F:22])[F:23])[C... | [O-][I+3]([O-])([O-])[O-] | CCSCC(O)(C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1)C(F)(F)F | null | [Na+] | null | null | 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 | null | 48 | A solution of sodium metaperiodate (0.407 g.) in water (15 ml.) was added dropwise to a stirred solution of 4-cyano-3-trifluoromethyl-N-(3-ethylthio-2-hydroxy-2-trifluoromethylpropionyl)aniline (0.6 g.) in methanol (25 ml.) and the mixture was stirred at laboratory temperature for 48 hours and then filtered. The solid ... | CCS(=O)CC(O)(C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1)C(F)(F)F | null | null | null |
162,160 | ord_dataset-c34472859da14a81bfe0f74e60f15c43 | null | 1987-01-01T00:08:00 | true | [CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:21][CH2:20]1)=[O:4].[C:32](Cl)(=[O:35])[CH2:33][CH3:34].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:32](=[O:35])[C... | CNC(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | CCC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2.22 g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide, 1.39 g of propionyl chloride, 2.53 g of triethylamine and 50 ml of toluene is refluxed for 2.5 days with stirring. The mixture is concentrated under reduced pressure to remove solvent. Water is added to... | CCC(=O)N(C)C(=O)N1CCSC1c1ccccc1OCCN1CCN(c2cccc(F)c2)CC1 | null | 12 | null |
1,730,327 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | O[C@H:2]([CH:22]([CH3:24])[CH3:23])[C@H:3]([NH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[NH:7][C@... | CC(C)[C@@H](O)[C@H](NC(=O)OCCCCCc1ccccc1)C(=O)O | null | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[B-](F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 15 | Under nitrogen atmosphere, to a stirred mixture of (2S*,3R*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid (0.14 g, 0.43 mmol) in dry CH2Cl2 (20 mL), at 0° C., Et3N (0.18 mL, 1.3 mmol) and subsequently TBTU (0.17 g, 0.55 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt fo... | CC(C)[C@@H]1OC(=O)[C@@H]1NC(=O)OCCCCCc1ccccc1 | null | 37.9 | null |
898,618 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [C:1]1([S:7]([CH2:10][C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:25]([O-])=O.[Na+].C([O-])(O)=O.[Na+].[ClH:34]>O>[ClH:34].[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([C:13]2[N:12]=[C:11]3[C:10]([S:7]([C:1]... | O=N[O-] | CN1CCN(c2ccc(N)c(CS(=O)(=O)c3ccccc3)n2)CC1 | null | Cl | O=C([O-])O | [Na+] | 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 | A stirred solution of 2-[(phenylsulfonyl)methyl]-6-(4-methylpiperazin-1-yl)-pyridin-3-ylamine (1.20 g, 3.50 mmol) in 1.0 M aqueous hydrochloric acid (20 mL) is cooled in an ice bath, treated dropwise with NaNO2 (358 mg, 5.2 mmol) in water, stirred for 1h, treated with aqueous saturated NaHCO3 and filtered. The brown so... | CN1CCN(c2ccc3[nH]nc(S(=O)(=O)c4ccccc4)c3n2)CC1 | null | null | null |
1,278,144 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | CC([N:5]([CH2:9][CH:10]([NH:18][C:19]([C:21]1[S:22][C:23]([Cl:33])=[C:24]([C:26]2[N:30]([CH2:31][CH3:32])[N:29]=[CH:28][CH:27]=2)[CH:25]=1)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(=O)[O-])(C)C.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[C:34]([OH:40])([C:36]([F:39])([F:38])[F:3... | CCn1nccc1-c1cc(C(=O)NC(Cc2ccccc2)CN(C(=O)[O-])C(C)(C)C)sc1Cl | 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 | null | 0.5 | 1,1-dimethylethyl[2-({[5-chloro-4-(1-ethyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate (61 mg, 0.12 mmol) was dissolved in DCM (2 mL) and treated with TFA (1 mL). After 0.5 h, the solution was concentrated and neutralized through silica using 4% MeOH in DCM (1% NH4OH). The title compound was fur... | CCn1nccc1-c1cc(C(=O)NC(CN)Cc2ccccc2)sc1Cl | null | 53 | null |
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