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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,658,883 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([CH:23]=O)[CH:17]=[CH:16]3)[CH2:2]1.[NH2:25][CH2:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].C(O)C.C([BH3-])#N.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[F:31][C:27]([F:32])([CH2:... | NCC(F)(F)C(=O)O | O=Cc1ccc2cc(OC3CCC4(CCCCC4)CC3)ccc2c1 | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [BH3-]C#N | [Na+] | 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 solution of 6-(spiro[5.5]undec-3-yloxy)-naphthalene-2-carbaldehyde (150 mg, 0.46 mmol) and 3-amino-2,2-difluoro-propionic acid (58.2 mg, 0.465 mmol) in ethanol (0.7 mL, 10 mmol) was heated to reflux for 2 h. The yellow solution was then cooled to room temperature and sodium cyanoborohydride (35.1 mg, 0.558 mmol) was ... | O=C(O)C(F)(F)CNCc1ccc2cc(OC3CCC4(CCCCC4)CC3)ccc2c1 | null | 41.4 | null |
1,364,029 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | CC(C)N=C=NC(C)C.[Cl:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][C:12]=1[NH:25][C:26]([NH:28][C:29]1[CH:30]=[C:31]([C:42](=[O:54])[NH:43][C@H:44]2[CH2:49][CH2:48][C@H:47]([C:50]([F:53])([F:52])[F:51])[CH2:46][CH2:45]2)[C:32]([O:37][CH2:38][CH:39]([F:41])[F:40... | CNc1nc(OCC(F)F)c(C(=O)N[C@H]2CC[C@H](C(F)(F)F)CC2)cc1NC(=S)Nc1cc(CNC(=O)C(C)(C)C)ccc1Cl | null | null | CC(C)N=C=NC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 60 | 8 | DIC (40 μL, 0.24 mmol) is added to a mixture of N-{4-chloro-3-[3-(trans-4-trifluoromethyl-cyclohexylcarbamoyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-pyridin-5-ylthioureido]benzyl}-2,2-dimethyl-propionamide (135 mg, 0.20 mmol) and MeCN (3.5 mL). The reaction mixture is stirred at 60° C. overnight, allowed to cool and co... | Cn1c(Nc2cc(CNC(=O)C(C)(C)C)ccc2Cl)nc2cc(C(=O)N[C@H]3CC[C@H](C(F)(F)F)CC3)c(OCC(F)F)nc21 | null | null | null |
1,504,729 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:26]C(OC(C)(C)C)=O)[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[O:10])=[CH:3][CH:2]=1.[ClH:40].O1CCOCC1>>[ClH:40].[NH2:26][C@@H:8]([CH2:7][C:4]1[CH:3]... | CC(C)(C)OC(=O)N[C@@H](Cc1ccc(-c2ccccc2)cc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | 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 | null | 1 | A solution of (S)-benzyl 1-((S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoyl)pyrrolidine-2-carboxylate (429 mg, 0.812 mmol) and HCl in 1,4-dioxane (2.03 ml, 8.12 mmol) was allowed to stir for 1 hour and concentrated under reduced pressure to give (S)-benzyl 1-((S)-2-amino-3-(biphenyl-4-yl)propanoyl)pyrrolidi... | N[C@@H](Cc1ccc(-c2ccccc2)cc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1 | null | null | null |
1,501,637 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][CH:24]=[C:25]([CH:46]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:38]([CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:39].[C:47]1([CH2:53]... | O=C(Nc1ccc2cc1CCc1cccc(c1)Nc1ncc(Cl)c(n1)N2)C1CCNCC1 | O=C(Cl)Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The desired compound was prepared according to the procedure of Example A20, using N-[6-chloro-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20), 3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]piperidine-4-carboxamide bis(trifluoroacetate) and benzeneacetyl chloride as starting materials in 70% yield. 1H NMR (30... | O=C(Nc1ccc2cc1CCc1cccc(c1)Nc1ncc(Cl)c(n1)N2)C1CCN(C(=O)Cc2ccccc2)CC1 | null | 70 | null |
1,753,219 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][N:2]([CH2:6][CH2:7][OH:8])[CH2:3][CH2:4][OH:5].[C:9]([OH:28])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[CH3:1][N:2]([CH2:6][CH2:7][O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:1... | CCCCCCCC/C=C\CCCCCCCC(=O)O | CN(CCO)CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Compound A-6 (333 mg, 51.4%) was obtained in the same manner as that in Reference Example 2, by using N-methyldiethanolamine (Tokyo Chemical Industry Co., Ltd.; 119 mg, 1.00 mmol) and oleic acid (Tokyo Chemical Industry Co., Ltd.; 621 mg, 2.20 mmol) | CCCCCCCC/C=C\CCCCCCCC(=O)OCCN(C)CCOC(=O)CCCCCCC/C=C\CCCCCCCC | null | null | null |
1,219,292 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][NH2:15])=[O:13])=[CH:10][CH:9]=2)[CH2:4]1.[O:19]([CH2:26][CH2:27][S:28][CH2:29][C:30](O)=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]3[O:13... | O=C(O)CSCCOc1ccccc1 | CN(C)C1CCN(c2ccc(C(=O)NN)cc2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-(3-Dimethylaminopyrrolidin-1-yl)benzohydrazide was reacted with (2-phenoxy-ethylsulfanyl)acetic acid by Method A. The product with the molecular weight of 424.57 (C23H28N4O2S) was obtained in this way; MS (ESI): 425 (M+H+). | CN(C)C1CCN(c2ccc(-c3nnc(CSCCOc4ccccc4)o3)cc2)C1 | null | null | null |
671,606 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]2([CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH:13]=O)[CH2:10][CH2:9]2)[CH:7]=1.[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[NH2:36])[N:27]=1)=[O:25]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]([C:26]1[CH:3... | COC(=O)c1ccc2c(N)cccc2n1 | COc1ccc(F)cc1C1(CC(O)(C=O)C(F)(F)F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | Analogously to Example 37, 306 mg (1.2 mmol) of 5-{3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanal is reacted with 170 mg (0.84 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester in 4.0 ml of concentrated acetic acid and 20 ml of toluene. After working-up and purification on s... | COC(=O)c1ccc2c(N=CC(O)(CC3(c4cc(F)ccc4OC)CC3)C(F)(F)F)cccc2n1 | null | null | null |
205,002 | ord_dataset-72fffaae67c8473fb9d951cb1b026646 | null | 1990-01-01T00:03:00 | true | [C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(#N)C>[CH:12]1([CH2:11][CH2:10][NH:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1 | NCc1ccccc1 | BrCCC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | Combine 10.7 g (0.1 mol) of benzenemethanamine and 17.7 g (0.1 mol) of (2-bromoethyl)cyclopentane in 100 mL of acetonitrile. Heat the mixture to reflux and follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction remove the solvent in vacuo and add 100 mL of satu... | c1ccc(CNCCC2CCCC2)cc1 | null | null | null |
108,831 | ord_dataset-d9235b0d1f9f4e85b2690ee8f860dc30 | null | 1983-01-01T00:09:00 | true | N[C:2]1[C:6]2[C:7]([OH:11])=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:13])(=[O:12])[N:3]=1.[OH-:14].[Na+].C.Cl>O>[OH:11][C:7]1[C:6]2[C:2](=[O:14])[NH:3][S:4](=[O:13])(=[O:12])[C:5]=2[CH:10]=[CH:9][CH:8]=1 | NC1=NS(=O)(=O)c2cccc(O)c21 | [OH-] | null | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | 5 gm (25.2 mmols) of 3-amino-4-hydroxy-1,2-benzoisothiazole-1,1-dioxide and 2.02 gm (50.5 mmols) of sodium hydroxide were refluxed in 15 ml of water for 6.5 hours. Subsequently, the solution was treated with activated charcoal at 60° C. and filtered. At 60° C. the filtrate was acidified with concentrated aqueous hydroc... | O=C1NS(=O)(=O)c2cccc(O)c21 | null | 92 | null |
1,437,374 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | C(OC(=O)[NH:10][CH2:11][C:12]1[N:21]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[CH3:29])[C:20](=[O:30])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)C1C=CC=CC=1.[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH3:29][C:23]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=... | Cc1ccc(-n2c(CNC(=O)OCc3ccccc3)nc3ccccc3c2=O)c(C)c1 | O=S(=O)(Cl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | [3-(2,4-Dimethylphenyl)-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]carbamic acid benzyl ester, as prepared above in Example 4, was hydrogenated in a similar manner as described above in Example 6, and then condensed, as described above in Paragraph A, with benzenesulfonyl chloride to yield N-[3-(2,4-dimethylphenyl)-4-oxo-3... | Cc1ccc(-n2c(CNS(=O)(=O)c3ccccc3)nc3ccccc3c2=O)c(C)c1 | null | null | null |
1,327,715 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.Cl[C:11]1[N:16]=[CH:15][C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>>[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][N:6]([C:11]2[N:16]=[CH:15][C:14]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=2)[CH:7]=1 | CCCC(=O)c1ccc(Cl)nc1 | FC(F)(F)c1cn[nH]c1 | null | O=C([O-])[O-] | [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 | 50 | 4 | A mixture of 4-(trifluoromethyl)pyrazole (116 mg, 0.85 mmol), 1-(6-chloropyridin-3-yl)butan-1-one (130 mg, 0.71 mmol), and potassium carbonate (294 mg, 2.12 mmol) was stirred 4 h at 50° C. The mixture was cooled to room temperature and stirred overnight. The mixture was partitioned between ethyl acetate and water. The ... | CCCC(=O)c1ccc(-n2cc(C(F)(F)F)cn2)nc1 | null | 99.4 | null |
1,553,021 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][OH:23])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26]>CO.C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:1... | C=CC(=O)OC(C)(C)C | OCC12CCC(c3cccc(Oc4ccccc4)c3)(CC1)OC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CO | null | null | null | null | null | null | null | null | null | 25 | 5 | A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methanol (50 mg, 0.161 mmol), tert-butyl acrylate (0.059 mL, 0.403 mmol), and Triton B (40% in MeOH) (7 μL, 0.016 mmol) in toluene (1 mL) was stirred at rt for 5 h. The mixture was concentrated in vacuo and the residue was purified by flash chromatography ... | CC(C)(C)OC(=O)CCOCC12CCC(c3cccc(Oc4ccccc4)c3)(CC1)OC2 | null | 86.4 | null |
397,557 | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | null | 1998-01-01T00:04:00 | true | [F:1][C:2]([F:40])([F:39])[CH2:3][NH:4][C:5]([C:7]1([CH2:20][CH2:21][NH:22][C:23]([N:25]2[CH2:30][CH2:29][CH:28]([NH:31][C:32](=O)[O:33]C(C)(C)C)[CH2:27][CH2:26]2)=[O:24])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].Cl.O1[CH2:47][CH2:46]OCC1>C1COCC1>[C:32]([NH:31][CH:... | C1COCCO1 | CC(C)(C)OC(=O)NC1CCN(C(=O)NCCC2(C(=O)NCC(F)(F)F)c3ccccc3-c3ccccc32)CC1 | 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 | 3 | To a solution of Example 487 compound (1.1 g, 1.97 mmol) in THF (4 mL) was added 4N HCl in dioxane (9 mL, 36.4 mmol). The reaction mixture was stirred at room temperature for 3 h and concentrated in vacuo and then from dioxane (3×10 mL) to give crude title compound (1.46 g) as a white foamy solid. | O=C(NC1CCN(C(=O)NCCC2(C(=O)NCC(F)(F)F)c3ccccc3-c3ccccc32)CC1)c1ccccc1 | null | null | null |
373,765 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [N+:1]([O-:4])(O)=[O:2].[CH:5]1([N:10]2[C:14]3=[N:15][C:16]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:17][C:18](=[O:19])[C:13]3=[C:12]([CH2:27][CH3:28])[NH:11]2)[CH2:9][CH2:8][CH2:7][CH2:6]1>>[CH:5]1([N:10]2[C:14]3=[N:15][C:16]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([N+:1]([O-:4])=[O:2])=[CH:25][CH:26]=4... | O=[N+]([O-])O | CCc1[nH]n(C2CCCC2)c2nc(Cc3ccccc3)nc(=O)c1-2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 1.5 | and (b) To 90% HNO3 (95 mL) at -10° to -15° C. was added 1-cyclopentyl-3-ethyl-6-(phenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one (9.62 g, 30 mmol). The reaction mixture was stirred as such for 1.5 hours, and then was poured into ice water. A precipitate formed which was collected by filtration, recrystallized from ethyl a... | CCc1[nH]n(C2CCCC2)c2nc(Cc3ccc([N+](=O)[O-])cc3)nc(=O)c1-2 | null | null | null |
1,308,356 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].OO.[OH-].[Na+].[ClH:15]>O>[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:15])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5] | NC(=O)c1cccnc1N | Cl | null | OO | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 60 | 1 | (Step 1) To a solution of 2-aminonicotinamide (0.5 g) in concentrated hydrochloric acid (3 ml) was added dropwise 30% aqueous hydrogen peroxide (0.3 ml). After stirring at 60° C. for 1 hr, the reaction mixture was diluted with water and basified with 1N aqueous sodium hydroxide solution. The mixture was extracted with ... | NC(=O)c1cc(Cl)cnc1N | null | null | null |
696,443 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:30][CH3:31])[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2[O:27][CH2:28][CH3:29])=[N:13][C:14]=1[CH2:15][CH3:16].N1C=CN=C[C:33]=1N>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:... | Nc1cnccn1 | CCO[C@H]1Cc2ccccc2[C@H]1Nc1nc(CC)c(-c2ccc(Cl)cc2Cl)nc1CC | null | null | null | null | null | null | null | 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 for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting (cis)-2-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]pyrazin-2-amine and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.1... | CCO[C@H]1CCc2ccccc2[C@H]1Nc1nc(CC)c(-c2ccc(Cl)cc2Cl)nc1CC | null | null | null |
786,102 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][O:1... | Cc1oc(-c2ccc(Cl)nc2)nc1CCO | Cc1ccc(S(=O)(=O)Cl)cc1 | null | CN(C)c1ccncc1 | null | 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 | null | 8 | The crude 2-[2-(6-Chloro-pyridin-3-yl)-5-methyl-oxazol-4-yl]-ethanol from step C is dissolved in methylene chloride (50 mL), then TsCl, DMAP and triethyl amine are added and stirred overnight. The reaction mixture is washed with water, brine and concentrated. Column chromatography on silica gel gave the title compound ... | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccc(Cl)nc3)oc2C)cc1 | null | null | null |
297,343 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | [Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:18](=[O:20])[CH3:19])[C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].[NH2:21]/[C:22](/[CH3:31])=[CH:23]\[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C(O)CCC>[C:18]([C:10]1[CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[C:23](... | CC(=O)C(=Cc1cccc(Cl)c1Cl)C(=O)CCCCCl | C/C(N)=C/C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCO | null | null | null | null | null | null | null | null | null | null | null | null | 25 g (70 mmol) 6-(2,3-dichlorophenyl-methylene)-1-chloro-5,7-octanedione and 22 g (0.14 mol) tert-butyl β-amino-crotonate are boiled under reflux in 200 ml 1-butanol for 6 h. The mixture is concentrated and the residue is prepurified by chromatography with toluene/acetone=8/2. The product thus obtained is chromatograph... | CC(=O)C1=C(CCCCCl)NC(C)=C(C(=O)OC(C)(C)C)C1c1cccc(Cl)c1Cl | null | null | null |
645,337 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])O)=[O:5])[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl.[OH-].[Na+]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[... | CCOC(=O)C1CC1C(O)c1ccc2[nH]cc(C#N)c2c1 | null | null | CC[SiH](CC)CC | [Na+] | [OH-] | 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 | A solution of the 2-[(3-cyano-1H-indol-5-yl)-hydroxy-methyl]-cyclopropane-carboxylic acid ethyl ester (1.0 g, 3.5 mmol), dichloromethane (25 ml), and trifluoroacetic acid (5 ml) was cooled to 0° C. and treated with triethylsilane (0.57 g, 5.0 mmol). The solution was stirred for 30 min and then diluted with an additiona... | CCOC(=O)C1CC1Cc1ccc2[nH]cc(C#N)c2c1 | null | 66 | null |
37,720 | ord_dataset-b0ddd49dad024fc7a23ae6f474f9c52f | null | 1978-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2N(C)C(=O)[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[CH3:21][O:22][C:23](=[O:26])OC>>[CH3:21][O:22][C:23]([C:9]1[NH:8][C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:6]2[C:5]=1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20]2)=[O:26] | CN1C(=O)CN=C(c2ccccc2)c2cc(Cl)ccc21 | COC(=O)OC | null | null | null | null | null | null | null | 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 starting material can be prepared from 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one and dimethylcarbonate in a manner analogous to that described in Example 1. After recrystallization from acetone, there is obtained 5-chloro-3-phenylisoindole-1-carboxylic acid methyl ester; melting point 208°-2... | COC(=O)c1[nH]c(-c2ccccc2)c2cc(Cl)ccc12 | null | null | null |
687,526 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]=O)[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][C:23](=[O:44])[CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:21]>ClCCl>[CH2:20]([O:22][C:23](=[O:44])/[CH:24]=[CH:17]/[C@H:14]1[CH2:15][CH2:16][C@H:11]([CH2:... | CN(CC[C@H]1CC[C@H](C=O)CC1)C(=O)OC(C)(C)C | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | 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 | null | A solution of 4.02 g (14.9 mmol) trans-[2-(4-formyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester and 5.47 g (14.9 mmol) of (triphenyl-phosphoranylidene)-acetic acid ethyl ester in 40 ml of dichloromethane was stirred at room temperature for 60 hours. After concentration under reduced pressure, the crude pro... | CCOC(=O)/C=C/[C@H]1CC[C@H](CCN(C)C(=O)OC(C)(C)C)CC1 | null | 75.5 | null |
1,767,133 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH:29][C:30]([NH:32][C@@H:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C@H:36]([O:43][C:44]3[CH:45]=[CH:46][C:47]4[N:48]([C:50]([N:53]5[CH2:58][CH2:57][CH2:56][CH2:55][C@@H:54]5[CH3:59])=[N:51][N:52]=4)[CH:49]=3)[CH2:35][CH2:34]2)=[O:31])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][Si:17](... | CS(=O)(=O)Cl | CC(C)[Si](Oc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CCCC[C@@H]5C)n4c3)c3ccccc32)cc1CO)(C(C)C)C(C)C | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 0 | 0.5 | A solution of Intermediate 61e (124 mg, 0.15 mmol) in DCM (1.5 mL) at 0° C. was treated with DIPEA (79 μL, 0.45 mmol) then methanesulfonyl chloride (23 μL, 0.30 mmol) and the mixture was stirred at RT for 1 h. The mixture was cooled to 0° C. and treated with another portion of DIPEA (40 μL, 0.23 mmol) and methanesulfon... | CC(C)[Si](Oc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)N[C@H]2CC[C@@H](Oc3ccc4nnc(N5CCCC[C@@H]5C)n4c3)c3ccccc32)cc1CCl)(C(C)C)C(C)C | null | 27 | null |
1,739,286 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Br:1][C:2]1[C:7]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9... | OCCBr | CCOc1ccc(Cc2cc([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c(Br)c(O)c2Cl)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 50 | 15 | To a solution of crude compound 78 (2.67 g, 3.1 mmol) in acetone (30 mL) were added 2-bromoethanol (0.33 mL, 4.63 mmol) and K2CO3 (640 mg, 4.63 mmol) at 0° C. The mixture was stirred at 50° C. for 15 hours. The mixture was filtrated and concentrated in vacuo. The resultant was partitioned between EtOAc and water. The o... | CCOc1ccc(Cc2cc([C@@H]3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c(Br)c(OCCO)c2Cl)cc1 | null | 95.2 | null |
594,006 | ord_dataset-278fb6af8a994ac69e4d95e6e6eff756 | null | 2003-01-01T00:05:00 | true | [H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:40]([CH3:41])[C:23]2=[N:24][C:25]([S:28][C:29]3[CH:34]=[C:33]([CH3:35])[C:32]([N+:36]([O-:38])=[O:37])=[C:31]([CH3:39])[CH:30]=3)=[CH:26][CH:27]=[C:22]2[N:21]=1>CN(C)C=O>[CH3:39][C:31... | O=C1NC(=O)C(Cc2ccc(O)cc2)S1 | Cc1cc(Sc2ccc3nc(CCl)n(C)c3n2)cc(C)c1[N+](=O)[O-] | 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 | 0.33 | To a suspension of sodium hydride (0.12 g, 55% w/w) in N,N-dimethylformamide (6 ml) was added 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (0.31 g). The mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added dropwise a solution of 2-chloromethyl-5-(3,5-dimethyl-4-nitrophenylthio)-3-methy... | Cc1cc(Sc2ccc3nc(COc4ccc(CC5SC(=O)NC5=O)cc4)n(C)c3n2)cc(C)c1[N+](=O)[O-] | null | null | null |
493,583 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [C:1]1([S:7]([C:10]2[C:11]([NH2:15])=[N:12][NH:13][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](OCC)(=O)[CH2:17][C:18]([CH3:20])=O>C(O)(=O)C>[C:1]1([S:7]([C:10]2[CH:14]=[N:13][N:12]3[CH:16]=[CH:17][C:18]([CH3:20])=[N:15][C:11]=23)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1 | Nc1n[nH]cc1S(=O)(=O)c1ccccc1 | CCOC(=O)CC(C)=O | 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 | A solution of 1.0 g (4.47 mmol) of 4-benzenesulphonyl-1H-pyrazol-3-ylamine and 0.6 ml (5.37 mmol) of ethyl acetoacetate in 8 ml of acetic acid was heated at reflux for 1.5 hrs. The reaction solution was cooled to RT and evaporated. The residue was partitioned between CH2Cl2 and H2O and the aqueous phase was washed thre... | Cc1ccn2ncc(S(=O)(=O)c3ccccc3)c2n1 | null | 74.5 | null |
1,557,223 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11](N)=[CH:12][C:7]=2[N:6]=[N:5]1.N([O-])=[O:17].[Na+]>OS(O)(=O)=O.O>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:7]=2[N:6]=[N:5]1 | O=N[O-] | CC(C)(C)Cn1nnc2cc(N)ccc21 | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution of 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (2-4, 150 mg, 0.734 mmol, 1.0 equv.) in 20% H2SO4 (5 mL), was slowly added sodium nitrite (70.8 mg, 1.026 mmol, 1.4 equiv.). The reaction mixture was stirred at room temperature until LCMS showed complete conversion to diazonium ion. The reaction sol... | CC(C)(C)Cn1nnc2cc(O)ccc21 | null | null | null |
1,095,913 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3]C(C)(C)C)=O.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1C(Cl)=O.C(N(CC)CC)C>ClCCl>[N:8]1([C:1]([C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[C:15]([F:26])([F:25])[F:14])=[O:3])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | O=C(Cl)c1ccccc1C(F)(F)F | CC(C)(C)OC(=O)N1CCNCC1 | null | null | null | 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 | 18 | To a stirred solution of 1-Boc-piperazine (1.96 g, 10.5 mmol) in dichloromethane (50 mL) was added 2-trifluoromethylbenzoyl chloride (2.09 g, 10.0 mmol) as a dichloromethane solution in the presence of triethylamine (3 mL) at 0° C. The resulting mixture was stirred at ambient temperature for 18 hours and then quenched ... | O=C(c1ccccc1C(F)(F)F)N1CCNCC1 | null | null | null |
1,533,865 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][C:12](=[O:34])[C@H:13]([NH:26]C(=O)OC(C)(C)C)[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:36])([CH3:35])[O:3]1>Cl.CCOC(C)=O>[NH2:26][C@H:13]([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:24])([... | CC(C)(C)OC(=O)N[C@H](CCc1ccc(C(F)(F)F)cc1)C(=O)Nc1ccc2c(c1)B(O)OC2(C)C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | (R)-tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-ylamino)-1-oxo-4-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (1.44 g, 2.844 mmol) was stirred with 4.4 M HCl/EtOAc (10 mL) at room temperature for 30 min. The solution was evaporated to dryness under vacuum to produce (R)-2-amino-N-(1-hydrox... | CC1(C)OB(O)c2cc(NC(=O)[C@H](N)CCc3ccc(C(F)(F)F)cc3)ccc21 | null | 96.7 | null |
1,274,718 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | Br[C:2]1[S:6][C:5]([C:7]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[C:14]([C:33]4[CH:48]=[CH:47][C:36]([C:37]([O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:38])=[CH:35][CH:34]=4)[N:15]3[CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]3=[O:32])=[CH:1... | CCOC(=O)Cc1cc(C(=O)c2ccc3cc(-c4ccc(C(=O)OCc5ccccc5)cc4)n(CCCCN4C(=O)c5ccccc5C4=O)c3c2)sc1Br | OB(O)c1cccc(O)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Cs+] | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOC | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5 (60 mg, 0.075 mmol), Pd(PPh3)4 (17 mg, 0.015 mmol), CsF (34 mg, 0.22 mmol), 3-hydroxyphenylboronic acid (16 mg, 0.12 mmol), and H2O (80 μL) in DME (8 mL) was degassed with N2 for 10 min and then refluxed. When the reaction was over by TLC monitoring, the mixture was poured into H2O (10 mL) and then extra... | CCOC(=O)Cc1cc(C(=O)c2ccc3cc(-c4ccc(C(=O)OCc5ccccc5)cc4)n(CCCCN4C(=O)c5ccccc5C4=O)c3c2)sc1-c1cccc(O)c1 | null | 81.6 | null |
1,183,493 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [Sn](Cl)(Cl)(Cl)Cl.[C:6](Cl)(=[O:8])[CH3:7].[S:10]1[C:14]([NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2.O>ClCCl>[C:6]([C:13]1[C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=2[S:10][C:14]=1[NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])(=[O:8])[CH3:7] | CCS(=O)(=O)Nc1cc2ccccc2s1 | CC(=O)Cl | null | Cl[Sn](Cl)(Cl)Cl | null | 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 | 25 | 0.08 | Tin (IV) chloride (173 μL, 1.48 mmol) was added to a solution of acetyl chloride (124 μL, 1.75 mmol) in dichloromethane (10 mL), at 0° C., and the resulting solution was stirred for 5 min. To the resulting mixture was then added a solution of ethanesulfonic acid benzo[b]thiophen-2-ylamide (325 mg, 1.35 mmol) in dichlor... | CCS(=O)(=O)Nc1sc2ccccc2c1C(C)=O | null | null | null |
1,262,402 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[C:11]([C:13]1[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH:20]=1)[C:18]#[N:19])#[CH:12].N>>[F:21][C:16]1[CH:15]=[CH:14][C:13]([C:11]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[CH:12]=2)=[CH:20][C:17]=1[C:18]#[N:19] | C#Cc1ccc(F)c(C#N)c1 | ON=C(Cl)c1cccnc1 | null | N | null | null | null | null | null | 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 titled compound was prepared according to Method CB using the product of Example 1A (78 mg, 0.5 mmol) and the product of Example 68A (73 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.49 (s, 1H), 7.52-7.68 (m, 2H), 8.28 (ddd, J=8.8, 5.1, 2.4 Hz, 1H), 8.33-8.41 (m, 2H), 8.68 (dd, J=4.9, 1.5 Hz, 1H), 9.09 (d, J=2.4 Hz,... | N#Cc1cc(-c2cc(-c3cccnc3)no2)ccc1F | null | null | null |
1,112,682 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][NH:25][CH2:26][CH3:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].Cl[C:30]1[O:31][C:32]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:33]=2[N:34]=1.C(N(C(C)C)CC)(C)C>CCO>[CH2:1]([O:3][... | Cc1ccc2oc(Cl)nc2c1 | CCNCc1cc(C(F)(F)F)ccc1-c1cc(CC(=O)OCC)ccc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 80 | 8 | (2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.300 g, 0.76 mmol), chloro-5-methyl-benzooxazole (0.135 g, 0.81 mmol), and diisopropylethylamine (0.5 mL, 2.87 mmol) were combined in EtOH (2 mL) in a sealed tube, and the reaction was stirred at 80° C. for 8 hours. The mixture w... | CCOC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(CC)c2nc3cc(C)ccc3o2)c1 | null | null | null |
125,132 | ord_dataset-6d96290c60d941d098c4ddc9d0cb01a0 | null | 1984-01-01T00:12:00 | true | [H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH:12]=[C:11]([C:14]([O:16]CC)=O)[CH:10]=[CH:9]2.[CH3:19][S:20][CH2:21][S:22]([CH3:24])=[O:23]>CN(C)C=O>[O:16]=[C:14]([C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:4]([Cl:3])[CH:5]=[CH:6][CH:7]=2)[CH:12]=1)[CH:21]([S:20][CH3:19])[S:22]([CH3:24])=[O:23] | CSCS(C)=O | CCOC(=O)c1ccc2cccc(Cl)c2c1 | 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 | 4 | A suspension of 9.2 g sodium hydride in 50 ml of N,N-dimethylformamide was added in one portion to a stirred solution of 5.6 g (24 mM) of ethyl 8-chloro-2-naphthylformate and 4.4 g (36 mM) of methyl methylthiomethyl sulfoxide in 10 ml of N,N-dimethylformamide. The reaction mixture was stirred for four hours at 25° C., ... | CSC(C(=O)c1ccc2cccc(Cl)c2c1)S(C)=O | null | 63.4 | null |
1,696,444 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C[O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:10]([OH:38])=[C:11]2[C:16](=[C:17]([C:19]3[N:20]=[CH:21][S:22][CH:23]=3)[N:18]=1)[N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14](=[O:31])[C:13]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:12]2)=[O:8].[OH-].[Na+].CO.C1COCC1>C([O-])(O)=O.... | COC(=O)CCNC(=O)c1nc(-c2cscn2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | null | O=C([O-])O | [Na+] | [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 | 25 | 16 | A mixture of 3-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-8-thiazol-4-yl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-propionic acid methyl ester (24 mg, 0.044 mmol), 2 M NaOH (3 mL), MeOH (3 mL) and THF (3 mL) was stirred at r.t. for 16 h, then concentrated to approximately one-third of its original volume. 1 M HCl was ... | O=C(O)CCNC(=O)c1nc(-c2cscn2)c2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | 56.1 | null |
576,682 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | NC(N)=O.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[C:22]([OH:29])=[C:23]([CH:25]=[CH:26][C:27]=2[Cl:28])[NH2:24])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[Cl:30][C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=1[N:38]=[C:39]=[O:40]>>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH... | O=C=Nc1cccc(Cl)c1Cl | CC(C)(C)OC(=O)N1CCN(S(=O)(=O)c2c(Cl)ccc(N)c2O)CC1 | null | NC(N)=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 | Following the general procedure for urea formation outlined in example 15, 3-[4-(tert- butoxycarbonyl)piperazin-1-yl]sulfonyl4-chloro-2-hydroxyaniline (110 mg, 0.28 mmol) and 2,3-dichlorophenylisocyanate (64 mg, 0.34 mmol) were coupled to form the desired urea (34 mg, 25%). EI-MS (m/z) 576.65, 578.65, 580.67 (M−). | CC(C)(C)OC(=O)N1CCN(S(=O)(=O)c2c(Cl)ccc(NC(=O)Nc3cccc(Cl)c3Cl)c2O)CC1 | null | 20.9 | null |
937,867 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([OH:20])=[N:8][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.[C:21]([O:25][C:26]([C@@H:28]1[CH2:32][C@@H:31](O)[CH2:30][C@H:29]1[C:34](=[O:46])[NH:35][C@:36]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:38][C@H:37]1[CH:39]=[CH2:40])=[O:... | C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@H](O)C[C@H]1C(=O)OC(C)(C)C)C(=O)OCC | COc1ccc2c(O)nc(-c3ccccc3)nc2c1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Quinazolinol derivative (83) (480 mg, 1.8 mmol) was coupled to compound 15 (0.55 mg, 1.5 mmol) as described in example 16, which gave the title compound (700 mg, 75%) | C=CC1CC1(NC(=O)C1CC(Oc2nc(-c3ccccc3)nc3c(C)c(OC)ccc23)CC1C(=O)OC(C)(C)C)C(=O)OCC | null | 75.8 | null |
1,568,269 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[S:22][C:21]([CH2:23][CH2:24][NH:25][C:26]([NH:28][NH:29]C(OC(C)(C)C)=O)=[O:27])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O1CCOCC1.Cl>>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17... | CC(=O)N1CCN(c2ccc(CCc3ccc(CCNC(=O)NNC(=O)OC(C)(C)C)s3)nc2)CC1 | 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 | null | null | By a method similar to Production Example 115, step 5, tert-butyl 2-{[2-(5-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}thiophen-2-yl)ethyl]carbamoyl}hydrazinecarboxylate (498.0 mg, 0.964 mmol) was deprotected with 4M hydrogen chloride dioxane solution. The crude product was purified by aminopropylated silica gel a... | CC(=O)N1CCN(c2ccc(CCc3ccc(CCNC(=O)NN)s3)nc2)CC1 | null | 42.5 | null |
1,527,816 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1.[CH3:29][C:30]1([CH3:44])[CH2:34][C:33]2[CH:35]=[C:36](/[CH:39]=[CH:40]/[C:41](O)=[O:42])[CH:37]=[CH:38][C:32]=... | CC1(C)Cc2cc(/C=C/C(=O)O)ccc2O1 | NC(=O)C(NC1CCC(c2c[nH]c3ccccc23)CC1)C1CCNCC1 | 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 title compound was prepared from the product of Example 1, step J, and (2E)-3-(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoic acid, by the method of Example 1, step K, giving a yellow solid that was a mixture of cyclohexyl diastereomers by LCMS. Mass spectrum (LCMS, ESI pos.) calcd. for C33H40N4O3: 541 (M+... | CC1(C)Cc2cc(/C=C/C(=O)N3CCC(C(NC4CCC(c5c[nH]c6ccccc56)CC4)C(N)=O)CC3)ccc2O1 | null | null | null |
127,513 | ord_dataset-e61c1950b2fc468dbf0701c65768f73f | null | 1985-01-01T00:03:00 | true | C(=O)=O.CC(C)=O.[NH3:8].C([O:11][C:12]([C:14]1[O:25][C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]([CH3:26])[C:16]=2[C:15]=1[O:27][CH3:28])=O)C>O1CCCC1>[CH3:28][O:27][C:15]1[C:16]2[N:17]([CH3:26])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]=2[O:25][C:14]=1[C:12]([NH2:8])=[O:11] | N | CCOC(=O)c1oc2c3ccccc3n(C)c2c1OC | null | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 16 | A flask fitted with a Dewar condenser containing dry ice/acetone was cooled in a dry ice/acetone bath and charged with 350 ml of anhydrous ammonia. A few crystals of hydrated ferric nitrate catalyst were added, and the cooling bath was removed. Lithium amide was then generated by the addition, over one hour, of 1.78 g ... | COc1c(C(N)=O)oc2c3ccccc3n(C)c12 | null | 79 | null |
1,495,493 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[N:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[CH:24][C:23]=2[CH3:31])=[O:21])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].O>ClCCl>[NH2:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[N:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[C:24]([Br:1])[C:23]... | O=C1CCC(=O)N1Br | COC(=O)c1cc(C(=O)c2c(C)cc3ccccn23)ccc1N | null | null | null | 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 | 2 | 0.492 g (2.73 mmol) of N-bromosuccinimide is added, under an inert atmosphere at ambient temperature, to 0.812 g (2.6 mmol) of methyl 2-amino-5-[(2-methylindolizin-3-yl)carbonyl]benzoate in 17 ml of dichloromethane. The reaction medium is stirred for 2 hours and then hydrolysed with water. The aqueous phase is extracte... | COC(=O)c1cc(C(=O)c2c(C)c(Br)c3ccccn23)ccc1N | null | 89.4 | null |
1,532,532 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:27])[NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[C:29]([CH3:36])([CH3:35])[C:30](OCC)=[O:31].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH... | CCOC(=O)C(C)(C)C1CC2(CCN(C(=O)NC3C4CC5CC(C4)CC3C5)CC2)c2c(Br)cccc21 | null | null | CC(C)C[AlH]CC(C)C | 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 | 0.5 | To a solution of (±)-ethyl 2-(7-bromo-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)-2-methylpropanoate (100 mg, 0.18 mmol) in anhydrous toluene was added DIBAL-H (0.4 mL, 1 M) at −78° C. The mixture was stirred for 30 min and quenched with MeOH. The organic layer was separated, dried and co... | CC(C)(C=O)C1CC2(CCN(C(=O)NC3C4CC5CC(C4)CC3C5)CC2)c2c(Br)cccc21 | null | null | null |
683,328 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [C:1]([N:8]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O=[Pt]=O.CO>[C:1]([N:8]1[CH2:16][C@@H:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH... | COC(=O)[C@@H]1C[C@H](c2ccccc2)CN1C(=O)OC(C)(C)C | null | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | A mixture of N-BOC-4(R)-phenyl-(L)-proline, methyl ester from Example 61, Step B (0.165 g, 0.54 mmol), PtO2 (0.1 g, 0.44 mmol) and MeOH was shaken under 50 psi of H2 overnight. The reaction was filtered through a pad of celite and concentrated in vacuo to afford N-BOC-4(R)-cyclohexyl-(L)-proline, methyl ester which was... | COC(=O)[C@@H]1C[C@H](C2CCCCC2)CN1C(=O)OC(C)(C)C | null | null | null |
10,221 | ord_dataset-53cd7fd33c6f4f1c804e187bec94be57 | null | 1976-01-01T00:07:00 | true | C([Cl:4])(=O)C.[CH3:5][C:6](/[CH:14]=[CH:15]/[CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:7][C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9]>>[Cl:4][C:21]([CH3:22])([CH3:23])[CH2:20][CH2:19][CH2:18][CH:17]([CH3:24])[CH2:16]/[CH:15]=[CH:14]/[C:6]([CH3:5])=[CH:7][C:8]([O:10][CH:11]([CH3:13])... | CC(=O)Cl | CC(C)=CCCC(C)C/C=C/C(C)=CC(=O)OC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.25 | To 40 ml. of ice cold isopropanol is added 2.49 g. of acetyl chloride. The resulting solution is stirred at 0° for 15 min. and 1.0 g. of trans isopropyl 3,7,11-trimethyldodeca 2,4,10-trienoate added. The solution is stirred for 1 hour at 0° and for 48 hours at 25°. Solvent is removed under reduced pressure and the conc... | CC(=CC(=O)OC(C)C)/C=C/CC(C)CCCC(C)(C)Cl | null | null | null |
1,697,361 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [Br:1][C:2]1[N:3]=[C:4]([C:18]([F:21])([F:20])[F:19])[N:5]2[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][C:6]=12.[ClH:22]>O1CCOCC1>[ClH:22].[Br:1][C:2]1[N:3]=[C:4]([C:18]([F:20])([F:19])[F:21])[N:5]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=12 | CC(C)(C)OC(=O)N1CCn2c(C(F)(F)F)nc(Br)c2C1 | 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 | null | 4 | Crude tert-butyl 1-bromo-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxylate 11b (470 mg, 1.27 mmol) was dissolved in 50 mL of a 2 M solution of hydrogen chloride in 1,4-dioxane. After stirring for 4 hours, the reaction mixture was concentrated under reduced pressure to obtain 1-bromo-3-(trifluorome... | FC(F)(F)c1nc(Br)c2n1CCNC2 | null | 56.5 | null |
519,838 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [OH: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][CH2:16][CH2:17][OH:18].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>N1C=CC=CC=1>[C:25]1([CH3:26])[CH:27]=[CH:28][C:22]([S:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2... | OCCCCCCCCCCCCCCCCO | Cc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748... | Cc1ccc(S(=O)(=O)OCCCCCCCCCCCCCCCCO)cc1 | null | null | null |
354,364 | ord_dataset-930bf31b476c482e8ba87824089eb600 | null | 1997-01-01T00:02:00 | true | N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>B(F)(F)F>[CH:2]1[C:6]2[C:6](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:5]=[CH:4][CH:3]=1 | c1ccncc1 | null | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Naphthalene was polymerized at a temperature of from 200° to 400° C. in the presence of a HF.BF3 catalyst to obtain a pitch which had an optical anisotropy of 100% as observed under a polarization microscope, an optical anisotropic structure of a "rough flow type", a Mettler softening point of 250° C. and an elemental ... | c1ccc2ccccc2c1 | null | null | null |
27,407 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | [C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>ClCCCl>[N+:10]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([OH:9])=[O:8])([O-:12])=[O:11] | O=[N+]([O-])O | O=C(O)c1ccccc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 40 | 3 | 61 g of benzoic acid were suspended in 200 ml of 1,2-dichloroethane. The suspension was heated to 40° C. following the addition of 38.6 g (0.60 mol) of 98% nitric acid. 63.5 g of 100% sulphuric acid were then added dropwise over a period of 2 hours at that temperature, followed by stirring for another 3 hours. After co... | O=C(O)c1cccc([N+](=O)[O-])c1 | null | null | null |
1,701,609 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | C(OC([N:6]1[CH2:27][CH2:26][C:10]2[C:11]3[CH:12]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.Br>C(O)(=O)C>[F:19][C:13]1([F:18])[CH:12]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:11]2[C:10]3[CH2:26][CH2:27][NH:6][CH2:7][CH2:8][C:9]=... | CCOC(=O)N1CCc2ccc3c(c2CC1)C(c1cccnc1)C(F)(F)C3 | null | null | Br | 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 | 60 | null | Into a 250 ml flask, the product from step (c) (3.7 g, 9.9 mmol) dissolved in acetic acid (50 ml) and HBr (33% in acetic acid, 50 ml) was added. The stirred reaction mixture was heated to 60° C. for 6 hours. The reaction mixture was cooled and the volatiles were evaporated in vacuo. The crude product was dissolved in w... | FC1(F)Cc2ccc3c(c2C1c1cccnc1)CCNCC3 | null | 94.2 | null |
1,481,396 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [Br:1][C:2]1[C:3]([C:8]([F:11])([F:10])[F:9])=[N:4][NH:5][C:6]=1[CH3:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([C:8]([F:9])([F:11])[F:10])=[N:4][N:5]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:24]2)[C:6]=1[CH3:7] | Cc1[nH]nc(C(F)(F)F)c1Br | C1=COCCC1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | O | null | null | null | null | null | null | null | null | null | 0 | 1.5 | A solution of 4-bromo-5-methyl-3-(trifluoromethyl)-1H-pyrazole (1.00 g, 4.37 mmol) and p-toluenesulfonic acid monohydrate (80 mg, 0.4 mmol) in CHCl3 (3.5 mL) was cooled to 0° C. and dihydropyran (480 μL, 5.2 mmol) was added dropwise. The reaction was stirred at 0° C. for 1.5 h. The solvent was removed in vacuo and the ... | Cc1c(Br)c(C(F)(F)F)nn1C1CCCCO1 | null | 86.2 | null |
267,537 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH2:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH2:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3])(=[O:21])[CH3:20] | C=Cc1ccc(C(C)(C)O)cc1 | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | A mixture of 6.7 g of 1-(1-hydroxy-1-methylethyl)-4-ethenyl-benzene and 4.0 g of pyridine in 100 ml of dichloromethane was stirred while 4.0 g of acetyl chloride in 20 ml of dichloromethane was added dropwise. After the addition was complete, the mixture was refluxed gently overnight. After cooling, an additional 30 ml... | C=Cc1ccc(C(C)(C)OC(C)=O)cc1 | null | 48 | null |
500,969 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13](Cl)=[O:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[NH2:16][CH:17]([C:37](N1CCCCC1)=[O:38])[CH2:18][NH:19][C:20](=[O:36])[CH2:21][NH:22][S:23]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)(=[O:25])=[O:24]>>[CH:27]1[C:28]2[C:33](=[CH... | NC(CNC(=O)CNS(=O)(=O)c1ccc2ccccc2c1)C(=O)N1CCCCC1 | O=C(Cl)C1CCN(c2ccncc2)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 | Using an analogous procedure to that described in Example 1, 1-(4-pyridyl)piperidine-4-carbonyl chloride was reacted with N-[2-amino-2-(piperidinocarbonyl)ethyl]-2-(2-naphthalenesulphonamido)-acetamide to give 2-(2-naphthalenesulphonamido)-N-{2-piperidino-carbonyl-2-[1-(4-pyridyl)piperidin-4-ylcarbonylamino]ethyl}aceta... | O=C(CNS(=O)(=O)c1ccc2ccccc2c1)NCC(NC(=O)C1CCN(c2ccncc2)CC1)C(=O)C1CCCCN1 | null | 41 | null |
1,215,342 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][C:2]1([C:7]2[N:8]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][C:15]([NH2:18])=[N:14]3)[S:10][CH:11]=2)[O:6]CCO1.[CH3:19][C:20]1[O:21][C:22]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)=[C:23]([C:25](O)=[O:26])[N:24]=1>>[C:2]([C:7]1[N:8]=[C:9]([CH2:12][N:13]2[CH:17]=[CH:16][C:15]([NH:18]... | CC1(c2csc(Cn3ccc(N)n3)n2)OCCO1 | Cc1nc(C(=O)O)c(-c2cccc(C(F)(F)F)c2)o1 | null | null | null | null | null | null | null | 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 B followed by C, starting from 1-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiazol-2-ylmethyl]-1H-pyrazol-3-ylamine and 2-methyl-5-(3-trifluoromethyl-phenyl)-oxazole-4-carboxylic acid. LC-MS-conditions 05: tR=0.96 min; [M+H]+=476.03. | CC(=O)c1csc(Cn2ccc(NC(=O)c3nc(C)oc3-c3cccc(C(F)(F)F)c3)n2)n1 | null | null | null |
692,512 | ord_dataset-35824232b132464aa99e71aba765981d | null | 2005-01-01T00:12:00 | true | C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH... | COc1ccc(CCc2ccc(Nc3ccccc3C(=O)O)cc2)cc1OC | 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 | 25 | 2 | To a solution of 2-{4-[2-(3,4-dimethoxy-phenyl)-ethyl]phenylamino}-benzoic acid (0.28 g, 0.74 mmol) in CH2Cl2 (20 mL), BBr3 (3.5 mL, 1M in CH2Cl2, 3.5 mmol) was added at room temperature under a N2 atmosphere. The reaction mixture was allowed to stir at room temperature for 2 hours and then poured into ice water (50 mL... | O=C(O)c1ccccc1Nc1ccc(CCc2ccc(O)c(O)c2)cc1 | null | 93.2 | null |
534,700 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [CH3:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[C:18]([NH:21][NH2:22])([NH2:20])=[NH:19].[ClH:23].Cl.O>C(O)C>[ClH:23].[NH:21]([N:22]=[C:10]1[CH2:9][CH:8]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]1=2)[C... | N=C(N)NN | Cc1ccnc2c1C(=O)CC(c1cccs1)C2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-methyl-7-(2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (0.52 g), aminoguanidine hydrochloride (0.25 g), concentrated hydrochloric acid (0.53 ml), water (0.53 ml) and ethanol (50 ml) was refluxed for 7 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The so... | Cc1ccnc2c1C(=NNC(=N)N)CC(c1cccs1)C2 | null | 79.4 | null |
952,856 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | C(O)(=O)C.[CH2:5]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:19]1([CH:15]2[CH2:16][CH2:17][N:12]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:13][CH2:14]2)[CH2:22][CH2:21][CH2:2... | C1CNC1 | O=C1CCN(Cc2ccccc2)CC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 12 | 1.0 mL (17.5 mmol) glacial acetic acid were added to the stirred mixture of 3.0 mL (16.5 mmol) 1-benzyl-4-piperidone, 1.0 g (17.5 mmol) azetidine and 100 mL DCM. Then 6.0 g (39.5 mmol) sodium triacetoxy-borohydride was added batchwise within one hour while cooling with an ice bath and the mixture was stirred for a furt... | c1ccc(CN2CCC(N3CCC3)CC2)cc1 | null | null | null |
195,348 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]1[C:18](=[O:19])[O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:18]([OH:17])=[O:19])(=[O:16])[C:20]1[CH:25]=[CH... | O=C1CCCCCCCCCCC(=O)O1 | c1ccccc1 | null | [Al+3] | [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 | 2.5 | To a stirred suspension of 18 gms AlCl3 (0.135 mole) in 150 ml dry benzene was added 13 gms 1,10-decanedicarboxylic anhydride in small portions over 15 minutes, then the mixture was refluxed for 6 hours. The solid was filtered off, stirred for 2.5 hours in 350 ml 2N HCl, removed by filtration, and stirred in 300 ml 1N ... | O=C(O)CCCCCCCCCCC(=O)c1ccccc1 | null | null | null |
160,465 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [OH:1][CH2:2][CH2:3][O:4][C:5]1[CH2:10][CH2:9]S[CH:7]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:6]=12.OO[S:20]([O-:22])=[O:21].[K+]>CO.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH2:10][CH2:9][S:20](=[O:22])(=[O:21])[CH:7]2[S:11][C:12]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:13][C:6]=12 | O=S([O-])OO | NS(=O)(=O)C1=CC2=C(OCCO)CCSC2S1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 8 | To a stirred solution of 5,6-dihydro-4-(2-hydroxyethoxy)thieno[2,3-b]thiopyran-2-sulfonamide (1.0 g, 0.0034 mole) in CH3OH (20 ml) was added dropwise a solution of OXONE® (3.15 g, 0.005 mole) in water (20 ml). The mixture was stirred at ambient temperature overnight and then filtered, washing the filter cake thoroughly... | NS(=O)(=O)C1=CC2=C(OCCO)CCS(=O)(=O)C2S1 | null | null | null |
1,688,087 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19](O)=[O:20])[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:22]([F:25])([F:24])[F:23])([O-:3])=[O:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:55][CH2:56][CH2:57][N:58]([CH2:70][CH2:71]Cl)[C:59]1[CH:68]=[CH:67][C:66]2[C:61](=[CH... | O=C(O)COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1 | NCCN(CCCl)c1ccc2cc(Cl)ccc2n1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | To a solution of 2-[(4-[4-nitro-3-(trifluoromethyl)phenyl]aminocyclohexyl)oxy]acetic acid (100 mg, 0.28 mmol) in dichloromethane (20 ml) was added EDAC.HCl (79.4 mg, 0.41 mmol, 1.5 eq), HOBt (56 mg, 0.41 mmol, 1.5 eq), triethylamine (111.6 mg, 1.10 mmol, 4 eq), and N-(2-aminoethyl)-6-chloro-N-(2-chloroethyl)quinolin-2-... | O=C(COC1CCC(Nc2ccc([N+](=O)[O-])c(C(F)(F)F)c2)CC1)N1CCN(c2ccc3cc(Cl)ccc3n2)CC1 | null | 42.1 | null |
244,626 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [H-].[Na+].O[C:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([CH2:25][O:6][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:24]=[CH:2... | CC(O)(O)c1ccc(OCc2ccc3ccccc3n2)cc1 | BrCc1ccccc1 | 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 | 18 | At 0° C., 50% NaH in oil (37 mg) was added portionwise to a solution of 1-hydroxy-1-(4-2(-quinolinylmethoxy)phenyl)ethanol (Step 1) (104 mg) and benzyl bromide (92 mg). Stirring was continued for 18 h and the reaction was quenched with 25% aqueous NH4OAc. The product was extracted with EtOAc, dried over MgSO4 and purif... | c1ccc(COCC(OCc2ccccc2)c2ccc(OCc3ccc4ccccc4n3)cc2)cc1 | null | null | null |
1,459,070 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:24]=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21.[CH:26]1([Mg]Br)[CH2:28][CH2:27]1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C... | Br[Mg]C1CC1 | COc1ccc(N2CCCn3c2nc2c(Cl)ccc(C=O)c23)c(Cl)c1 | null | [Cl-] | [NH4+] | 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 | 0 | 0.5 | To a solution of 9-chloro-1-(2-chloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (274 mg, 0.728 mmol) in tetrahydrofuran (10 mL) was added cyclopropylmagnesium bromide in tetrahydrofuran (1.0 M, 2.2 mL, 2.2 mmol) at 0° C. The mixture was stirred at 0° C. for 0.5 hr. Aqueous ammonium ... | COc1ccc(N2CCCn3c2nc2c(Cl)ccc(C(O)C4CC4)c23)c(Cl)c1 | null | 77 | null |
1,512,492 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:33](=[O:34])[C:12]2=[CH:13][N:14]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[CH:31][CH:30]=[N:29]4)=[CH:24][CH:23]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10]1.C(N(C(C)C)CC)(C)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH3:44][S:4... | O=c1c2cn(Cc3ccc(-n4cccn4)cc3)c3ccccc3c-2nn1-c1ccccc1CO | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | -78 | 0.5 | 2-[2-(Hydroxymethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 654, 0.23 g, 0.51 mmol) was suspended in dichloromethane (5 mL), treated with diisopropylethylamine (0.20 mL, 1.1 mmol, 2.2 equiv) and cooled to −78° C. Methanesulfonyl chloride (60 μL, 0.77 mmol, 1.5... | CS(=O)(=O)OCc1ccccc1-n1nc2c3ccccc3n(Cc3ccc(-n4cccn4)cc3)cc-2c1=O | null | null | null |
1,738,805 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH:17](N1CCCCC1)=[O:18].C(O)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([CH:17]=[O:18])=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1 | O=CN1CCCCC1 | Clc1ccnc(Cl)c1 | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CC(=O)O | null | null | null | null | null | null | null | null | null | -78 | 1 | To a solution of 2,4-dichloropyridine (10 g) in THF (100 mL) was added dropwise lithium diisopropylamide solution (2M, 37 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added dropwise 1-formylpiperidine (7.7 g) at −78° C. The reaction mixture was stirred at −78° C. for ... | O=Cc1c(Cl)ccnc1Cl | null | 58.9 | null |
666,004 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][N:21]=2)=[CH:4][CH:3]=1.[OH-].[K+].CO.Cl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]... | COC(=O)c1ccc(-c2cc3cc(S(C)(=O)=O)ccc3n2Cc2ccc(F)cc2)nc1 | null | null | Cl | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-(4-fluorobenzyl)-5-methanesulfonyl-2-(5-methoxycarbonylpyridin-2-yl)indole (0.37 g), potassium hydroxide (0.12 g) and methanol (40 ml) was heated under reflux for 3 hours under nitrogen atmosphere. To the reaction solution was added water and the mixture was neutralized with hydrochloric acid. The precip... | CS(=O)(=O)c1ccc2c(c1)cc(-c1ccc(C(=O)O)cn1)n2Cc1ccc(F)cc1 | null | 97.7 | null |
82,995 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | Cl.[Cl-].[CH:3]([NH2+:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([C:24]([NH2:26])=[O:25])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:5])[CH3:4]>C(OCC)C>[CH:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([C:24]([NH2:26])=[O:25])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=... | CC(C)[NH2+]CCCCC(C(N)=O)c1ccccc1-c1ccccc1 | null | null | Cl | [Cl-] | 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 | null | null | A solution of 4.9 g. of N-isopropyl-5-cyano-5-(1,1'-biphenyl-2-yl)pentylaminium chloride in 18.0 g. of conc. sulfuric acid containing 2.0 g. of water was heated at 100° C. for three hours. After cooling the reaction mixture to 5° C., the mixture was made alkaline by the addition of 10% sodium hydroxide. The alkaline so... | CC(C)NCCCCC(C(N)=O)c1ccccc1-c1ccccc1 | null | null | null |
174,762 | ord_dataset-4937da99a6a247eb90fa70f0d2eac3db | null | 1988-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10](=O)[CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1 | O=c1cc(-c2ccc(F)cc2)c2ccccc2[nH]1 | O=P(Cl)(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 | null | null | A mixture of 12 g of 4-(4-fluorophenyl)carbostyril and 50 ml of phosphorus oxychloride is heated under reflux for 1.5 hours and then concentrated under reduced pressure. Ice-water is added to the residue and the resulting mixture is extracted with chloroform. The organic layer is dried over anhydrous sodium sulfate and... | Fc1ccc(-c2cc(Cl)nc3ccccc23)cc1 | null | null | null |
176,654 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | [CH2:1]([N:8]1[CH2:12][CH:11](N)[CH:10](C)[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16](=O)[CH3:17].Cl>[Pd].O>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:9][N:8]([CH2:16][CH3:17])[CH2:1][CH3:2])[CH2:10][C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | CC=O | CC1C(=O)N(Cc2ccccc2)CC1N | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 11.5 g (0.056 mol) of (-)-1-benzyl-4-amino-methyl-pyrrolidin-2-one, 130 ml of water, 13 g of acetaldehyde, 5.8 ml of concentrated hydrochloric acid and 6.5 g of 20% palladium-on-charcoal was hydrogenated for 51/4 hours at 5 bar and at 25° C. The reaction mixture was filtered, the filtrate was evaporated, t... | CCN(CC)CC1CC(=O)N(Cc2ccccc2)C1 | null | null | null |
445,079 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:3]=1.Br[CH2:17][CH3:18]>>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:17][CH3:18])[N:5]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:3]=1 | Cc1cc(C)nc(-n2c(C)ccc2C)c1 | CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By analogy to Example 53, Step B, the anion of 4,6-dimethyl-2-(2,5-dimethylpyrrol-1-yl)pyridine was alkylated with bromoethane to give 4-methyl-2-(2,5-dimethylpyrrol-1-yl)-6-propylpyridine. | CCCc1cc(C)cc(-n2c(C)ccc2C)n1 | null | null | null |
544,533 | ord_dataset-d31180f42ced44719fd9e72685c798bf | null | 2002-01-01T00:05:00 | true | [NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[CH3:11]CCCCC.C[Si](C=[N+]=[N-])(C)C>ClCCl.CO>[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1 | CCCCCC | NC1CCC(C(=O)O)CC1 | null | C[Si](C)(C)C=[N+]=[N-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 21 | To a solution of 4-amino-1-cyclohexanecarboxylic acid (500 mg) in dichloromethane (20 mL) and methanol (10 mL) was added 10% hexane solution of trimethylsilyldiazomethane (638 mg), and the mixture was stirred for 21 hours at ambient temperature. The mixture was evaporated in vacuo to give methyl 4-amino-1-cyclohexaneca... | COC(=O)C1CCC(N)CC1 | null | null | null |
1,250,145 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[C:8]([CH3:21])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[NH:22]1[CH2:25][CH2:24][CH2:23]1>>[N:22]1([C:16]([C:15]2[CH:14]=[N:13][C:12]([O:11][CH2:10][C:9]3[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=3[CH3:21])=[CH:20][CH... | CCCCc1noc(C)c1COc1ccc(C(=O)O)cn1 | C1CNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 19b, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) was converted, using azetidine instead of L-2,2,2-trifluoro-1-(methyl)ethylamine, to the title compound (45 mg, 39%) which was obtained as a light yellow oil after purification by chromatography (silica, heptane:e... | CCCCc1noc(C)c1COc1ccc(C(=O)N2CCC2)cn1 | null | 39 | null |
1,531,706 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | Cl.[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]([F:15])[F:14])=[CH:9][C:8]=2[C:16]2[C:17]3[NH:24][C:23]([CH3:25])=[C:22]([C:26]([NH:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[O:27])[C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:4][CH2:3]1.[C:35](Cl)(=[O:37])[CH3:36]>>[C:35]([N:32]1[CH2:31][CH2:30][CH:29]([NH... | CC(=O)Cl | Cc1[nH]c2c(-c3cc(C(F)F)ccc3OCC3CC3)ncnc2c1C(=O)NC1CCNCC1 | 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 | Starting from 4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-(piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide hydrochloride (example D.f60) and commercially available acetyl chloride the title compound is obtained as colorless solid. | CC(=O)N1CCC(NC(=O)c2c(C)[nH]c3c(-c4cc(C(F)F)ccc4OCC4CC4)ncnc23)CC1 | null | null | null |
534,687 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [CH3:1][C:2]1[C:11]2[C:10](=O)[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.O>C(O)C>[ClH:25].[NH:23]([N:24]=[C:10]1[CH2:9][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH2:7][C:6]2[N:5]=[CH:4][... | N=C(N)NN | Cc1ccccc1C1CC(=O)c2c(C)ccnc2C1 | null | Cl | null | 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 mixture of 4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.30 g), aminoguanidine hydrochloride (0.14 g), concentrated hydrochloric acid (0.018 ml), water (0.018 ml) and ethanol (30 ml) was refluxed for 7 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water.... | Cc1ccccc1C1CC(=NNC(=N)N)c2c(C)ccnc2C1 | null | 97.5 | null |
1,644,393 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=2[N:6]=1.FC(F)(F)C(O)=O.[NH:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)(=[O:35])=[O:34])[CH2:21][CH2:20]1>>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([N:19]3[CH2:2... | Clc1ccc2oc(Cl)nc2c1 | O=S(=O)(Nc1ccccc1OC1CCNCC1)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Compound 24 is prepared using synthesis method 3 using intermediates 2h and 6a (yield: 92%). | O=S(=O)(Nc1ccccc1OC1CCN(c2nc3cc(Cl)ccc3o2)CC1)c1ccccn1 | null | null | null |
1,417,095 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20... | NCc1ccncc1 | CCOC(=O)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=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 | This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-(aminomethyl)pyridine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 12.40 (1H, br), 11.31 (1H, br), 10.15 (1H, br), 8.48 (2... | O=C(NCc1ccncc1)c1c(O)c2ncc(Cc3ccc(F)cc3)cc2[nH]c1=O | null | null | null |
1,302,245 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[C:15]([CH2:16]C)=[C:14](F)[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].[NH2:19][C@@H:20]([C:24]([OH:26])=[O:25])[C@@H:21]([CH3:23])[OH:22].O>CS(C)=O>[Cl:7][C:8]1[C:15]([CH3:16])=[C:14]([NH:19][C@H:20]([C@H:21]([OH:22])[CH3:23])[C:24]([OH:26])=[O:25])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11] | CCc1c(F)ccc(C#N)c1Cl | C[C@@H](O)[C@@H](N)C(=O)O | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 80 | 72 | K2CO3 (3.15 g, 22.8 mmol) was added to a solution of 2-chloro-3-ethyl-4-fluorobenzonitrile (2.1 g, 11.4 mmol) and D-allo-threonine (2.04 g, 17.1 mmol) in DMSO (25 mL) at room temperature The reaction mixture was heated to 80° C. and stirred for 72 h then allowed to cool to room temperature. H2O (200 mL) was added and t... | Cc1c(N[C@@H](C(=O)O)[C@@H](C)O)ccc(C#N)c1Cl | null | 47 | null |
527,688 | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | null | 2001-01-01T00:12:00 | true | [H-].[Na+].[Si:3]([O:10][C@@H:11]1[C@H:15]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@@H:14]([CH2:24][O:25][CH3:26])[O:13][C@H:12]1[N:27]1[CH:35]=[N:34][C:33]2[C:28]1=[N:29][C:30]([CH2:51][OH:52])=[N:31][C:32]=2[NH:36][CH2:37][CH:38]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:... | COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(CO)nc32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | BrCc1ccccc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | Sodium hydride (23 mg of an 80% dispersion in mineral oil, 0.76 mmol) was added to a stirred solution of {9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol (550 mg, 0.76 mmol) (preparation 15) in tetrahydrofuran (3 ml). Th... | COC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(COCc4ccccc4)nc32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C | null | 10.6 | null |
1,451,977 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C@@H:14]([C:16]2[CH:17]=[C:18](B(O)O)[C:19]([F:22])=[N:20][CH:21]=2)[CH3:15])[C@@H:10]([CH3:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:28]1[N:33]=[C:32]([CH3:34])[N:31]=[C:30]([N:35]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[CH2:36][C:3... | COc1ccc(CN(Cc2ccc(OC)cc2)c2cc(Cl)nc(C)n2)cc1 | C[C@H](c1cnc(F)c(B(O)O)c1)N1CCN(C(=O)OC(C)(C)C)C[C@@H]1C | null | CC(=O)[O-] | [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 | 120 | null | A glass microwave reaction vessel was charged with (5-((1R)-1-((2S)-4-(tert-butoxycarbonyl)-2-methyl-1-piperazinyl)ethyl)-2-fluoro-3-pyridinyl)boronic acid (Example 272, Step 2) (0.530 g, 1.443 mmol), 6-chloro-N,N-bis(4-methoxybenzyl)-2-methylpyrimidin-4-amine (Example 177) (0.554 g, 1.443 mmol), PdCl2 (AmPhos)2 (0.102... | COc1ccc(CN(Cc2ccc(OC)cc2)c2cc(-c3cc([C@@H](C)N4CCN(C(=O)OC(C)(C)C)C[C@@H]4C)cnc3F)nc(C)n2)cc1 | null | 24.8 | null |
1,726,559 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | C([O:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:15][C:16]=1[CH3:17])(=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[O:15][C:16]([CH3:17])=[C:12]([CH2:11][CH2:10][OH:9])[N:13]=2)=[CH:23][CH:22]=1 | Cc1oc(-c2ccc(F)cc2)nc1CCOC(=O)c1ccccc1 | null | null | [Na+] | [OH-] | 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 intermediate, 2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethyl benzoate (19.5 g, 60 mmol) was dissolved in 70 ml ethanol and stirred. 10% sodium hydroxide solution (NaOH: 4.8 g, 120 mmol) was slowly added dropwise, and the mixture was stirred overnight at room temperature. After the reaction was completed, the ethan... | Cc1oc(-c2ccc(F)cc2)nc1CCO | null | null | null |
247,917 | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | null | 1992-01-01T00:05:00 | true | [F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:9]([O:11][CH:12]=[CH:13][C:14](Cl)=[O:15])[CH3:10]>N1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:14](=[O:15])[CH:13]=[CH:12][O:11][CH2:9][CH3:10] | CCOC=CC(=O)Cl | Nc1ccccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-fluoroaniline (ex. Aldrich) (3 g) in pyridine (20 ml) was treated at 0° with 3-ethoxyacryloyl chloride (3.64 g) (Prepared according to Paul et al, U..S. Pat. No. 2,768,174, (1956)). After 30 minutes at 0°-10° the reaction mixture was partitioned between ether and water and worked-up in conventional fash... | CCOC=CC(=O)Nc1ccccc1F | null | 17.7 | null |
1,584,419 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=[N:14]O.S(Cl)(Cl)=[O:17]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([CH:8]3[CH2:13][CH:6]([NH:14][C:5]2=[O:17])[CH2:7]3)=[CH:10][C:11]=1[F:12] | ON=C1c2cc(Br)c(F)cc2C2CC1C2 | O=S(Cl)Cl | 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 | null | null | Into a 100-mL round-bottom flask was placed a solution of 6-Bromo-7-fluoro-2,3-dihydro-1H-1,3-methano-naphthalen-4-one oxime (3.5 g, 12.96 mmol, 1.00 equiv) in 1,4-dioxane (30 mL) and thionyl chloride (24.7 g, 207.56 mmol, 16.00 equiv). The resulting solution was heated to reflux for 6 h, cooled, concentrated under vac... | O=C1NC2CC(C2)c2cc(F)c(Br)cc21 | null | 88.6 | null |
399,761 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH2:1]([O:3][P:4]([CH:9]1[N:14]2[C:15](=[O:28])[C:16](=[O:27])[NH:17][C:18]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[C:21]([NH2:22])=[C:12]([C:13]=32)[CH2:11][CH2:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>>[CH2:6]([O:5][P:4]([CH:9]1[N:14]2[C:15](=[O:28])[C:16](=[O:27])[NH:17]... | CCOP(=O)(OCC)C1CCc2c(N)c(C(F)(F)F)cc3[nH]c(=O)c(=O)n1c23 | COC1CCC(OC)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 211 mg of 8-amino-9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid diethyl ester and 66 mg of 2,5-dimethoxytetrahydrofuran are reacted for one hour at 140° C. bath temperature. After recrystallization from ethanol, 123 mg of 8-(1-pyrrolyl)-9-trifluoromethyl-2,3-dioxo-1,2,3... | CCOP(=O)(OCC)C1CCc2c(-n3cccc3)c(C(F)(F)F)cc3[nH]c(=O)c(=O)n1c23 | null | null | null |
484,694 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [C:1]([N:4]([CH2:9][C:10]([OH:12])=O)[CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[OH2:13]>C(O)(=O)C>[C:6]([CH2:5][N:4]1[CH2:2][C:1](=[O:3])[N:4]([CH2:5][C:6]([OH:8])=[O:7])[CH2:9][C:10]1=[O:12])([OH:7])=[O:13] | CC(=O)N(CC(=O)O)CC(=O)O | O | 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 | 195 | null | N-acetyliminodiacetic acid (XVI) monohydrate (45 g) and varying amounts of water and acetic acid were heated at 175° C. or 195° C. for various periods of time. After cooling to room temperature, the mixture was filtered. The solid was washed with water (10 mL) and dried to give 1,4-di(carboxymethyl)-2,5-diketopiperazin... | O=C(O)CN1CC(=O)N(CC(=O)O)CC1=O | null | null | null |
1,375,235 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH2:12][CH:13]([C:18]1[C:22]([CH:23]2[CH2:25][CH2:24]2)=[C:21]([CH:26]2[CH2:29][CH:28]([CH2:30][CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:27]2)[O:20][N:19]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:11].[OH-].[Na+:37]>C(O)C>[Na+:37].[Cl:1][C:2]1[CH:7]=[C:... | CCC(CC)CC1CC(c2onc(C(CC(=O)O)CC(=O)Nc3ccc(C)cc3Cl)c2C2CC2)C1 | null | null | [Na+] | [OH-] | 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 | 0.33 | 4-(2-Chloro-4-methylphenylcarbamoyl)-3-{4-cyclopropyl-5-[3-(2-ethylbutyl)cyclobutyl]isoxazol-3-yl}butanoic acid (28.9 mg) and ethanol (1 mL) were mixed. To the mixture was added aqueous 1 N sodium hydroxide (0.0577 mL) at ice temperature. The mixture was stirred at ice temperature 20 min., and then the solvent was evap... | CCC(CC)CC1CC(c2onc(C(CC(=O)[O-])CC(=O)Nc3ccc(C)cc3Cl)c2C2CC2)C1 | null | null | null |
1,696,059 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | CO[C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:8]2)=[O:4].[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>>[CH2:15]([N:11]1[C:12]2[C:7](=[C:6]([OH:29])[C:5]([C:3]([NH:30]... | COC(=O)c1ncc2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | NCC(=O)O | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (162 mg, 0.42 mmol), glycine (2.11 g, 28 mmol) and NaOMe solution (42 mL, 21 mmol, 0.5M in MeOH) was refluxed for 32 h. After the mixture was cooled to r.t., the solvent was evaporated in vacuo. The residue was ... | O=C(O)CNC(=O)c1ncc2c(cc(-c3ccccc3)c(=O)n2Cc2ccccc2)c1O | null | 72.6 | null |
374,015 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | C(OC([N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH:9]1[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15])=O)(C)(C)C.O1CCOCC1.[ClH:27]>CO>[ClH:27].[N:16]1([C:14]([CH:9]2[CH2:10][S:11][CH2:12][CH2:13][NH:8]2)=[O:15])[CH2:17][CH2:18][CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCSCC1C(=O)N1CCCC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 4-(t-butoxycarbonyl)-3-(pyrrolidine-1-carbonyl)thiomorpholine (3.2 g) was dissolved in 50 ml of methanol. A 4N 1,4-dioxane solution of hydrogen chloride (13.1 ml) was added, and the solution was condensed to yield white crystals. These crystals was recrystallized from ethanol and diethyl ether to give 2.47 g (96%) of 3... | O=C(C1CSCCN1)N1CCCC1 | null | 96 | null |
1,394,246 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:5]([CH:6]=O)[C:4]=1[OH:13].CC1(C)O[C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1>O>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([CH:6]=[C:19]([C:17]([OH:18])=[O:16])[C:20](=[O:21])[O:13]2)=[CH:8][CH:9]=1 | CC1(C)OC(=O)CC(=O)O1 | COc1ccc(C=O)c(O)c1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 75 | 2 | 3,4-dimethoxy-salicylaldehyde (252.8 mg, 1.39 mmol) and Meldrum's acid (200 mg, 1.39 mmol) were combined in H2O (2 mL). The solution was stirred at 75° C. for 2 h. After cooling to room temperature, the precipitate was filtered and dried at suction to give 271.0 mg of 7,8-dimethoxy-3-carboxy-coumarin in an 78% yield. | COc1ccc2cc(C(=O)O)c(=O)oc2c1OC | null | 77.9 | null |
1,173,176 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1>ClCCl>[C:1]1([NH:7][NH:8][C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=C1CCC(=O)O1 | NNc1ccccc1 | 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 | 25 | 16 | 2.5 g (23 mmol) of phenylhydrazine were dissolved in 30 ml of dichloromethane and 2.3 g (23 mmol) of succinic anhydride were added portionwise. The reaction mixture was stirred at room temperature for 16 h. The precipitated product was isolated by filtration and washed with dichloromethane. Yield: 4.2 g. | O=C(O)CCC(=O)NNc1ccccc1 | null | null | null |
204,809 | ord_dataset-72fffaae67c8473fb9d951cb1b026646 | null | 1990-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O>[CH3:10][C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1)=[O:11] | CC(=O)OC(C)=O | Nc1cccc(O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 0 | null | To a stirred solution of 66.0 g (0.60 mole) of 3-aminophenol in 180 mL of water was added dropwise 77.9 g (0.76 mole) of acetic anhydride. After complete addition, the reaction mixture was heated on a steam bath for 10 minutes, then cooled to 0° C. A precipitate formed and was collected by filtration. The filter cake w... | CC(=O)Nc1cccc(O)c1 | null | 89.3 | null |
1,392,329 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [Br:1][C:2]1[CH:21]=[C:20]([F:22])[C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:23])[CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37]O)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[Br:1][C:2]1[CH:3]=[C:4]([F:23])[C:5]... | CC(C)(C)OC(=O)N1CCC(CO)CC1 | COc1cc2c(Nc3c(F)cc(Br)cc3F)ncnc2cc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using an analogous procedure to that described in the preparation of the starting material in Example 8, 4-(4-bromo-2,6-difluoroanilino)-7-hydroxy-6-methoxyquinazoline (1 g, 2.62 mmol) was reacted with 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (845 mg, 3.93 mmol), (prepared as described for the starting materia... | COc1cc2c(Nc3c(F)cc(Br)cc3F)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | null | 40.8 | null |
1,181,234 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1 | CS(=O)(=O)N1CCC(O)(c2ccc(Br)cc2)CC1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | 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 | 100 | 16 | A mixture of 4-(4-bromo-phenyl)-1-methanesulfonyl-piperidin-4-ol (60.00 g, 179.51 mmol) and p-toluenesulfonic acid (9.37 g, 53.85 mmol) in toluene (1.08 L) is stirred at 100° C. for 16 h. The reaction is cooled to 23° C. and successively washed with 2 M aq. sodium hydroxide to pH 10, and water. The phases are separated... | CS(=O)(=O)N1CC=C(c2ccc(Br)cc2)CC1 | null | 61.7 | null |
669,508 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | C([O:3][C:4](=O)/[C:5](/[F:29])=[C:6](\[C:9]1[C:18]([O:19][CH2:20][CH3:21])=[C:17]([Br:22])[C:16]2[C:15]([CH3:24])([CH3:23])[CH2:14][CH:13]=[C:12]([CH:25]([CH2:27][CH3:28])[CH3:26])[C:11]=2[CH:10]=1)/[CH2:7][CH3:8])C.[H-].C([Al+]CC(C)C)C(C)C>>[Br:22][C:17]1[C:16]2[C:15]([CH3:24])([CH3:23])[CH2:14][CH:13]=[C:12]([CH:25]... | CCOC(=O)/C(F)=C(/CC)c1cc2c(c(Br)c1OCC)C(C)(C)CC=C2C(C)CC | null | null | CC(C)C[Al+]CC(C)C | [H-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described in General Procedure G-1, (2E)-3-(4-bromo-8-sec-butyl-3-ethoxy-5,5-dimethyl-5,6-dihydronaphthalen-2-yl)-2-fluoro-pent-2-enoic acid ethyl ester (Compound A-132, 567 mg, 1.18 mmol) and diisobutylaluminum hydride (1M in methylene chloride, 2.84 mL, 2.84 mmol) were reacted to give the title compound as a color... | CCOc1c(/C(CC)=C(/F)CO)cc2c(c1Br)C(C)(C)CC=C2C(C)CC | null | null | null |
1,114,708 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH3:1][C:2]1([CH3:29])[CH2:7][CH:6]([C:8]2[C:16]3[C:11](=[C:12]([C:24]([NH2:26])=[O:25])[CH:13]=[C:14]([C:17]4[CH:21]=[C:20]([CH:22]=O)[S:19][CH:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:5][CH2:4][S:3]1(=[O:28])=[O:27].[NH:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(... | CC1(C)CC(c2c[nH]c3c(C(N)=O)cc(-c4csc(C=O)c4)cc23)CCS1(=O)=O | C1CCCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CC(=O)O | null | null | null | null | null | null | null | null | null | 100 | 0.42 | 3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (40 mg, 0.093 mmol) was dissolved in dimethyl sulfoxide (1.5 mL) and put in a microwave vial. The mixture was stirred and acetic acid (0.056 mg, 0.929 μmol) was added, hexahydro-1H-azepine (0.453 mL, 4.02 mmol) was a... | CC1(C)CC(c2c[nH]c3c(C(N)=O)cc(-c4csc(CN5CCCCCC5)c4)cc23)CCS1(=O)=O | null | 25.1 | null |
1,579,381 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[S:17][C:13]=3[C:12](=[O:24])[N:11]([CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[C:10]2=[O:38])[CH:5]=[N:4]1)[CH3:2].[ClH:39]>O1CCOCC1>[ClH:39].[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14]3... | CCn1cc(Cn2c(=O)n(C3CCN(C(=O)OC(C)(C)C)CC3)c(=O)c3sc(-c4ccccc4)cc32)cn1 | 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 | Tert-butyl 4-{1-[(1-ethyl-1H-pyrazol-4-yl)methyl]-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate (763 mg; compound B18) is dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml, 4.0 M). The solution is stirred for 1 h at RT. The resulting precipitate is filtered off,... | CCn1cc(Cn2c(=O)n(C3CCNCC3)c(=O)c3sc(-c4ccccc4)cc32)cn1 | null | null | null |
1,738,100 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH:21]1[C:30]2[CH2:29][CH2:28][CH2:27][C:26](=[O:31])[C:25]=2[CH:24]=[CH:23][N:22]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:26]3([OH:31])[CH2:27][CH2:28][CH2:29][C:30]4[CH:21]=[N:22][CH:23]=[CH:24]... | O=C1CCCc2cnccc21 | Fc1ccc(-c2nccs2)cc1 | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 0.33 | To a solution of DIPA (0.424 g, 4.2 mmol) in dry THF at −78° C. was added n-BuLi (0.268 g, 4.2 mmol) dropwise at −78° C., and the mixture was stirred for 30 min to produce LDA. A solution of 2-(4-fluorophenyl)thiazole (0.510 g, 2.8 mmol) in dry THF at −78° C. was then added to the above LDA solution. 7,8-Dihydroisoquin... | OC1(c2cnc(-c3ccc(F)cc3)s2)CCCc2cnccc21 | null | 46 | null |
894,484 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[CH:4][CH:3]=1.[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].N1CCCC1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([N:14]2[CH2:15][CH2:16][CH2:13][CH2:12]2)=[O:9])=[CH:10][CH:11]=1 | CCN(CC)CC | O=C=NCc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCNC1 | CC#N | null | null | null | null | null | null | null | null | null | null | null | A solution of 4-bromobenzylisocyanate (408 mg, 1.92 mmol) in acetonitrile (15 ml) was treated with triethylamine (390 mg, 3.86 mmol) followed by pyrrolidine (137 mg, 1.93 mmol) at room temperature with stirring under argon. The reaction was stirred at 20° C. for 30 minutes and then partitioned between ethyl acetate (10... | O=C(NCc1ccc(Br)cc1)N1CCCC1 | null | 99.7 | null |
999,807 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([CH2:15][OH:16])[CH:14]=[C:8]2[CH2:7]1>[O-2].[Mn+4].[O-2].C(Cl)(Cl)Cl>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:8]2[CH2:7]1 | OCc1cc2n(n1)CCN(C1=NCCS1)C2 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | The activated manganese (IV) oxide (16.75 g) was added to the mixture of chloroform (180 ml) solution of [5-(4,5-dihydrothiazol-2-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl]-methanol (3.35 g) at room temperature. The reaction mixture was refluxed for 1 hour. After refluxing, the mixture was filtered through a pa... | O=Cc1cc2n(n1)CCN(C1=NCCS1)C2 | null | null | null |
1,704,800 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[C:1]1([NH:7][C:8]2[O:9][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | NC(=O)Nc1ccccc1 | CCOC(=O)C(=O)CBr | 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 | 25 | null | A solution of 1-phenylurea (2.0 g, 14.69 mmol) and ethyl 3-bromo-2-oxopropanoate (2.16 ml, 14.69 mmol) in DMF (58 ml) was heated at 60° C. for 3 hours. The reaction mixture was allowed to cool to rt and quenched with water (300 ml)/Na2CO3-solution (50 ml). The product was extracted with EA (2×). The combined organic ph... | CCOC(=O)c1coc(Nc2ccccc2)n1 | null | null | null |
1,466,176 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9]C2C=C(C(F)(F)F)C3C(=CC=C(O[C@H]4CC[C@H](C(C)(C)C)CC4)C=3)N=2)[CH2:6]1)=[O:4].[C:35]([C@H:39]1[CH2:44][CH2:43][C@H:42]([O:45][C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[C:51](C=O)[CH:52]=3)[N:47]=2)[CH2:41][CH2:40]1)([CH3:38])([CH3:37])[CH3:36]>>[CH3:1][O:2][C:3]([CH... | COC(=O)C1CN(Cc2cc(C(F)(F)F)c3cc(O[C@H]4CC[C@H](C(C)(C)C)CC4)ccc3n2)C1 | CC(C)(C)[C@H]1CC[C@H](Oc2ccc3cc(C=O)ccc3n2)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 | Synthesized as per 1-[6-(trans-4-tert-Butyl-cyclohexyloxy)-4-trifluoromethyl-quinolin-2-ylmethyl]-azetidine-3-carboxylic acid methyl ester using 2-(trans-4-tert-Butyl-cyclohexyloxy)-quinoline-6-carbaldehyde as starting material. ESI-MS (M+H+): 411.30. | COC(=O)C1CN(Cc2ccc3nc(O[C@H]4CC[C@H](C(C)(C)C)CC4)ccc3c2)C1 | null | null | null |
645,223 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[CH3:1][O:2][NH:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1 | CON=Cc1ccc(C(F)(F)F)cc1 | null | null | [BH3-]C#N | [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 | Reduction 4-trifluoromethyl-benzaldehyde O-methyloxime of with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil (73% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.49 (3H, s, OCH3), 4.09 (2H, s, NCH2), 5.80 (1H, broad s, NH), 7.48 (2H, m, aromatics), 7.60 (2H... | CONCc1ccc(C(F)(F)F)cc1 | null | 73 | null |
932,149 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH2:14][NH:15][CH2:16][C@@H:17]([OH:32])[C@@H:18]([NH:28][C:29](=[O:31])[CH3:30])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:38]([O:40]CC)=[CH2:39])CCC.[ClH:51]>C1(C)C=CC=CC=1.CCOCC>[Cl... | C=C(OCC)[Sn](CCCC)(CCCC)CCCC | CC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CNCc1cc(Br)ccc1-c1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCOCC | null | null | null | null | null | null | null | null | null | 100 | 0.33 | To N-[(1S,2R)-3-{[(4-bromo-1,1′-biphenyl-2-yl)methyl]amino}-1-(3,5-difluorobenzyl)-2-hydroxypropyl]acetamide (120 mg, 0.24 mmol) in toluene (1 mL) was added tributyl(1-ethoxyvinyl)tin (100 μL, 0.28 mmol) and bis-triphenylphoshine palladium(II) dichloride (10 mg, 0.012 mmol), and the reaction was heated at 100° C. 3 h u... | CC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H](O)CNCc1cc(C(C)=O)ccc1-c1ccccc1 | null | null | null |
606,511 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14]Br)([CH3:4])([CH3:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][N:17]=[N+:18]=[N-:19])([CH3:4])([CH3:3])[CH3:2] | [N-]=[N+]=[N-] | CC(C)(C)OC(=O)Cc1ccccc1CBr | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 65 | 3 | To a solution of crude 2-bromomethylphenylacetic acid t-butyl ester (0.349 mol) in 600 mL DMF was added 34.1 g (0.524 mol) sodium azide and the mixture stirred at 65° C. for 3 h. After cooling to ambient temperature, the mixture was diluted with 1.2 L ethyl acetate. The organic layer was washed with water (3×800 mL), d... | CC(C)(C)OC(=O)Cc1ccccc1CN=[N+]=[N-] | null | null | null |
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