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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
832,857 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [P:1]([O:13][CH2:14][C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[S:36][C:37]([CH2:40][C:41]([NH:43][C:44]4[CH:49]=[CH:48][C:47]([F:50])=[C:46]([F:51])[CH:45]=4)=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:52][CH3:53])([O:8... | COc1cc2c(Nc3ncc(CC(=O)Nc4ccc(F)c(F)c4)s3)ncnc2cc1OCCCN1CCC[C@@H]1COP(=O)(OC(C)(C)C)OC(C)(C)C | 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 | Di(tert-butyl) ((2R)-1-(3-((4-((5-(2-((3,4-difluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl phosphate (450 mg, 0.58 mmol) in dioxane (20 ml) was treated with a solution of HCl (4N) in dioxane (940 μl) at ambient temperature for 15 hours. The solid was ... | COc1cc2c(Nc3ncc(CC(=O)Nc4ccc(F)c(F)c4)s3)ncnc2cc1OCCCN1CCC[C@@H]1COP(=O)(O)O | null | 70 | null |
611,350 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].C(O)(=O)C>C(O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:18][CH3:19] | COc1ccc([C@@H]2CCCC[C@@H]2[N+](=O)[O-])cc1OC | null | null | [Zn] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCO | null | null | null | null | null | null | null | null | null | null | null | 125 g of (+/−)-cis-1,2-dimethoxy-4-(2-nitrocyclohexyl)benzene and 120 g of zinc powder or granules are suspended in 1300 ml of ethanol. 220 ml of acetic acid are added dropwise at boiling heat. The precipitate is filtered off with suction and washed with ethanol, and the filtrate is concentrated under reduced pressure.... | COc1ccc([C@@H]2CCCC[C@@H]2N)cc1OC | null | 88.4 | null |
1,055,252 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([O:26]CC2C=CC=CC=2)[CH:25]=1)[C:19]([O:21][CH3:22])=[O:20].C([O-])=O.[NH4+]>CO.[Pd]>[OH:26][C:24]1[CH:23]=[C:18]([CH:17]=[C:16]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:14])[N:8]([CH3:1... | COC(=O)c1cc(OCc2ccccc2)cc(Oc2ccc3c(c2Cl)OCCN(C)C3=O)c1 | null | null | [Pd] | O=C[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of methyl 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(phenylmethyl)oxy]benzoate (8.8 g, 18.8 mmol), and ammonium formate (11.87 g, 188 mmol) in methanol (190 mL) was placed under an atmosphere of argon and 10% palladium on charcoal (880 mg) added. The mixture was heated under... | COC(=O)c1cc(O)cc(Oc2ccc3c(c2)OCCN(C)C3=O)c1 | null | 50.4 | null |
1,337,577 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][N:21]3[C:26]4([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH2:25][CH2:24][CH2:23][C:22]3=[O:32])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[C:40]1[O:41][C:42]2[CH:48]=[CH:47][CH:46]=[CH... | Clc1nc2ccccc2o1 | Cc1ccc(S(=O)(=O)n2ccc3c(CN4C(=O)CCCC45CCNCC5)cccc32)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | null | To the stirred solution of 1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one (TFA salt) (300 mg, 0.55 mmol) in DMF (6 mL) were added K2CO3 (380 mg, 2.75 mmol) and 2-chloro benzoxazole (101 mg, 0.66 mmol). The mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to rt and concentrated ... | Cc1ccc(S(=O)(=O)n2ccc3c(CN4C(=O)CCCC45CCN(c4nc6ccccc6o4)CC5)cccc32)cc1 | null | 79.9 | null |
1,704,455 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Cl.[Si]([O:9][CH2:10]/[C:11](/[CH3:43])=[CH:12]\[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[S:20]([N:23]([C:28]1[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:36]2[C:31]([CH:32]3[CH2:42][CH:33]3[CH2:34][O:35]2)=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21])(C(C)(C)C)(C)C>CO>[F:19][C:17]1[CH:16]=[CH... | COC(=O)c1c(N(C(=O)OC)S(=O)(=O)c2ccc(F)cc2/C=C(/C)CO[Si](C)(C)C(C)(C)C)ccc2c1OCC1CC21 | null | null | Cl | 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 | 0.75 | Concentrated hydrochloric acid (1 mL) was added to a solution of methyl (1aRS,7bSR)-5-(N-{2[(Z)-3-(tert-butyldimethylsilanyloxy)-2-methylprop-1-enyl]-4-fluorobenzenesulfonyl]-N-methoxycarbonyl-amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 202, 0.385 g) in methanol (20 mL) and the mixture ... | COC(=O)c1c(N(C(=O)OC)S(=O)(=O)c2ccc(F)cc2/C=C(/C)CO)ccc2c1OCC1CC21 | null | 100 | null |
1,475,479 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)[CH:7]=[CH:6][C:5]=12.[Cl:26]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:26][C:3]1[N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:... | Cn1cc(-c2ccc3ncc(Cc4ccc5nccn5c4)n3n2)cn1 | O=C1CCC(=O)N1Cl | 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 | 22 | 3-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 10, 33.6 mg, 0102 mmol) was dissolved in DCM (1 mL) with N-chlorosuccinimide (15 mg, 0.112 mmol). The RM was stirred at rt for 22 h. The solvent was removed. The residue was purified by preparative HPLC with acetonitrile a... | Cn1cc(-c2ccc3ncc(Cc4ccc5ncc(Cl)n5c4)n3n2)cn1 | null | null | null |
172,118 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [CH3:1][C:2]([C:6]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH3:15])[CH3:14])[CH2:8][N:7]=1)([S:4][CH3:5])[CH3:3].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[CH3:3][C:2]([C:6]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH3:15])[CH3:14])[CH2:8][N:7]=1)([S:4]([CH3:5])=[O:24])[CH3:1] | O=C(OO)c1cccc(Cl)c1 | CSC(C)(C)C1=NCN(C(C)C)C(=O)O1 | null | null | null | 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 | 25 | 1 | 11.5 g of 6-(1-methyl-1-methylmercaptoethyl)-3-isopropyl-3,4-dihydro-2H-1,3,5-oxadiazin-2-one (Example 1) are dissolved in 100 ml of chloroform. The resultant solution is cooled to -10° C., and a solution of 9.5 g of m-chloroperbenzoic acid in 120 ml of chloroform is then added dropwise. The reaction mixture is subsequ... | CC(C)N1CN=C(C(C)(C)S(C)=O)OC1=O | null | null | null |
212,484 | ord_dataset-e6e5ffd5405c481d8061087049155f9f | null | 1990-01-01T00:07:00 | true | [C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C[Si]([C:30]#[N:31])(C)C.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:1]([C:30]#[N:31])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1 | C[Si](C)(C)C#N | COc1ccc(C(=O)Cl)cc1 | null | Cl[Sn](Cl)(Cl)Cl | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | 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 | p-Anisoyl cyanide was prepared according to the general procedure reported by G. A. Olah et al. [supra]. Under dry conditions, 1.8740 g of p-anisoyl chloride (99%, Aldrich) (10.98 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.7 mL of trimethylsilyl cyanide (13 mmo... | COc1ccc(C(=O)C#N)cc1 | null | 90 | null |
1,062,516 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1.[Na].Cl[C:17]1[C:18]([N+:34]([O-:36])=[O:35])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:21]=[CH:20]2>C1COCC1>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([... | COC(=O)Cc1ccc(O)c(OC)c1 | C[Si](C)(C)CCOCn1ncc2c([N+](=O)[O-])c(Cl)ccc21 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | To methyl-3-methoxy-4-hydroxyphenylacetate (0.062 g, 0.32 mmol) in dry THF (5 mL) under nitrogen was added sodium hexamethyldisylazide (1M solution in THF) (312 μl, 0.31 mmol). After 10 min. stirring at room temperature 5-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (93 mg, 0.28 mmol) in 5 mL of THF ... | COC(=O)Cc1ccc(Oc2ccc3c(cnn3COCC[Si](C)(C)C)c2[N+](=O)[O-])c(OC)c1 | null | null | null |
1,486,736 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.[NH:19]1[CH2:23][CH2:22][CH2:21][C@@H:20]1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[N:25]1([CH2:24][C@H:20]2[CH2:21][CH2:22][CH2:23][N:19]2[C:13]([C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:... | C1CN[C@@H](CN2CCCC2)C1 | CC1(C)OB(c2ccc(C(=O)O)cc2)OC1(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 | null | [(2R)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone was prepared as described in Example 14 from 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid and (R)-(−)-1-(2-pyrrolidinylmethyl)pyrrolidine. | CC1(C)OB(c2ccc(C(=O)N3CCC[C@@H]3CN3CCCC3)cc2)OC1(C)C | null | null | null |
156,287 | ord_dataset-36f7bef430f14c2e8db5e3f7c3640d9b | null | 1987-01-01T00:04:00 | true | [C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([CH3:30])[C:17]([O:19][CH2:20][CH2:21][S:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:18]>CN(C)C=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH:16]([CH3:30])[C:17]([O:19][CH2:20][CH2:21][S:22][CH2:23][C:24]2[CH:29]=[... | Oc1ccc(O)cc1 | CC(Br)C(=O)OCCSCc1ccccc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | 12.1 g of hydroquinone were dissolved in 60 ml of dry dimethylformamide, and while blowing a slow stream of nitrogen into the solution, 31.7 g of potassium carbonate were added thereto at room temperature whilst stirring. Then the mixture was heated to 90° to 95° C. for one hour with stirring. The mixture was cooled to... | CC(Oc1ccc(O)cc1)C(=O)OCCSCc1ccccc1 | null | null | null |
836,740 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]2[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH:9]=2)[CH:7]=1.[Sn](Cl)Cl.Cl>CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:10]2[CH:9]=[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:25][CH... | COc1ccc(Cl)cc1-c1cc(Nc2ccc([N+](=O)[O-])cc2)nc(N)n1 | null | null | Cl | Cl[Sn]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 0.25 | A mixture of the title compound of Example 11 (0.060 g, 0.16 mmol) and tin (II) chloride (0.19 g, 1.0 mmol) in a solution of 1.0 M hydrochloric acid and methanol (1:10, 15 ml) was heated under reflux for 2 hours. After evaporation of volatiles under reduced pressure, the residue was treated with aqueous sodium hydroxid... | COc1ccc(Cl)cc1-c1cc(Nc2ccc(N)cc2)nc(N)n1 | null | 64 | null |
231,616 | ord_dataset-67c9ee844bf341888b345c8e36183b40 | null | 1991-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:18])[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=O.[Br-].[CH2:20]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:21][CH3:22]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:18])[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)... | CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CC(C(=O)c1cccnc1)c1ccc(Cl)cc1Cl | null | [Br-] | null | null | null | null | null | 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 2-(2,4-dichlorophenyl)-1-(3-pyridyl)-1-propanone and propyltriphenylphosphonium bromide there is obtained 3-(2,4-dichloro-β-methyl-α-propylidenephenethyl)-pyridine | CCC=C(c1cccnc1)C(C)c1ccc(Cl)cc1Cl | null | null | null |
164,802 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [CH3:1][O:2][N:3]=[C:4]([C:10](=[O:13])[CH2:11][CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].S(Cl)([Cl:17])(=O)=O>C(O)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:10](=[O:13])[CH:11]([Cl:17])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6] | O=S(=O)(Cl)Cl | CCOC(=O)C(=NOC)C(=O)CC | 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 | 2.5 | A mixture of ethyl 2-methoxyimino-2-propionylacetate (14.7 g.), sulfuryl chloride (10.9 g.) and acetic acid (14.7 ml.) was stirred at room temperature for an hour and then at 40° C. for 2.5 hrs. Ice-water was added to the reaction mixture, adjusted to pH 6.5 and extracted with methylene chloride. The extract was washed... | CCOC(=O)C(=NOC)C(=O)C(C)Cl | null | 91.9 | null |
1,729,731 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [OH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[CH3:8][C:9]([Si:12](Cl)([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(Cl)Cl>[C:9]([Si:12]([CH3:14])([CH3:13])[O:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])([CH3:11])([CH3:10])[CH3:8] | CC(C)(C)[Si](C)(C)Cl | CC(O)CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | 3-Hydroxy-butyric acid (500 mg, 4.8 mmol) is dissolved in a mixture of TBSCl (1.5 g, 10.1 mmol) in dry DCM (48 mL). The resulting mixture is stirred overnight at room temperature. The resulting suspension is then filtered and the obtained residues are washed with DCM, then stirred in Et2O and filtered. The obtained fil... | CC(CC(=O)O)O[Si](C)(C)C(C)(C)C | null | null | null |
407,952 | ord_dataset-d5bb2294ac964841b8ffc9e0a34e93af | null | 1998-01-01T00:07:00 | true | Cl[CH2:2][CH2:3][CH:4]([N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)[C:5]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([O:19][CH3:20])[C:9]([O:17][CH3:18])=[N:10]2.[CH3:26][C:27]([NH2:31])([CH3:30])[CH2:28][CH3:29]>C(O)C>[Cl:15][C:14]1[C:5]([CH:4]([CH2:3][CH2:2][NH:31][C:27]([CH3:30])([CH3:26])[CH2:28][CH3... | COc1nc2cc(Cl)c(Cl)c(C(CCCl)n3cccn3)c2nc1OC | CCC(C)(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 105 | null | A mixture of 5-[(2-chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline (150 mg, 0.37 mmol), 1,1-dimethyl-1-propylamine (3 mL) and ethanol (5 mL) were heated in a closed vessel at 105° C. for 7 hours. The mixture was cooled, the solvent was removed under reduced pressure, and the residue was dissolved ... | CCC(C)(C)NCCC(c1c(Cl)c(Cl)cc2nc(OC)c(OC)nc12)n1cccn1 | null | 38 | null |
223,176 | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | null | 1991-01-01T00:02:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[CH2:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=1)[CH3:9]>>[Br:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:8][CH3:9])=[CH:11][CH:12]=1 | CCc1ccc(CCO)cc1 | BrCCCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | (2.19 g) T.l.c. [K] Rf 0.48, from 1,5-dibromopentane (7.8 g) and 4- ethylbenzeneethanol (1.7 g). | CCc1ccc(CCOCCCCCBr)cc1 | null | null | null |
1,064,091 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:13]2[CH:14]=[C:10]([C:9]#[C:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)[N:11]=[C:12]2[CH3:15])=[C... | Fc1ccc(CBr)cc1 | Cc1cc(C#Cc2c[nH]c(C)n2)ccn1 | null | null | null | null | null | null | null | 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, MS: m/e=306.2 (M+H+), was prepared in accordance with the general method of example 1 from 2-methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine and 4-fluoro-benzylbromide. | Cc1cc(C#Cc2cn(Cc3ccc(F)cc3)c(C)n2)ccn1 | null | null | null |
241,287 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]=[C:9]=[S:10])=[O:7])=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]>O1CCCC1>[NH2:18][C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[NH:13][C:9](=[S:10])[NH:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:... | O=C(N=C=S)c1ccc(Cl)cc1 | NC(=O)c1ccccc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 3 | To a stirred mixture of 10.5 g of 4-chlorobenzoyl isothiocyanate in 100 ml of tetrahydrofuran was added a mixture of 6.8 g of 2-aminobenzamide in 200 ml of tetrahydrofuran. After stirring for 3 hours the solid was collected, giving 14.3 g of N-[[[2-(aminocarbonyl)phenyl]amino]thioxomethyl]-4-chlorobenzamide. | NC(=O)c1ccccc1NC(=S)NC(=O)c1ccc(Cl)cc1 | null | 85.8 | null |
79,797 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:18](O)(=[O:20])[CH3:19]>>[C:18]([C:3]1[C:4](=[O:12])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:20])[CH3:19] | CC(=O)O | O=c1cc(O)c2ccccc2o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0 | null | 120 g of 4-hydroxycoumarin in 600 ml of glacial acetic acid are heated to the boil and 380 ml of phosphorus oxychloride are added dropwise in the course of 60 minutes at the boil. The reaction mixture is heated to the boil under reflux for a further 30 minutes and is cooled and discharged into 4 l of ice-water. The cry... | CC(=O)c1c(O)c2ccccc2oc1=O | null | null | null |
150,778 | ord_dataset-b9a9e369e9da4413999591aa08f4c3e3 | null | 1986-01-01T00:11:00 | true | [C:1]([C:4]1[C:5](Cl)=[C:6]2[CH:12]=[N:11][N:10]([CH2:13][CH3:14])[C:7]2=[N:8][CH:9]=1)(=[O:3])[CH3:2].Cl.[NH2:17]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C>[CH2:13]([N:10]1[C:7]2[N:8]=[CH:9][C:4]3[C:5](=[N:17][O:3][C:1]=3[CH3:2])[C:6]=2[CH:12]=[N:11]1)[CH3:14] | NO | CCn1ncc2c(Cl)c(C(C)=O)cnc21 | null | Cc1ccc(S(=O)(=O)O)cc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 5-Acetyl-4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine (4.60 g) was refluxed for 2 hours in 450 ml of glacial acetic acid containing 15 g of hydroxylamine hydrochloride and 1.0 g of p-toluenesulfonic acid monohydrate. At the end of this time the reaction volume was reduced to ca. 200 ml under reduced pressure and then it... | CCn1ncc2c3noc(C)c3cnc21 | null | null | null |
450,251 | ord_dataset-3bcdb559226a40d89406474c02d082d1 | null | 1999-01-01T00:12:00 | true | C[Si](I)(C)C.[OH:6][NH:7][C:8](=[O:42])[C@H:9]([NH:25][S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)(=[O:28])=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OCC1C=CC=CC=1)=O.CO>C(#N)C>[OH:6][NH:7][C:8](=[O:42])[C@H:9]([NH:25][S:26]([N:29]1[CH2:30][CH2:31]... | O=C(NCCCC[C@@H](NS(=O)(=O)N1CCN(c2ccc(Cl)cc2)CC1)C(=O)NO)OCc1ccccc1 | null | null | C[Si](C)(C)I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC#N | null | null | null | null | null | null | null | null | null | 25 | null | Trimethylsilyl iodide (0.026 ml, 0.19 mmol) was added to a solution of N-hydroxy-6-(benzyloxycarbonyl)amino-2-(R)-{[4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}hexanoamide (103 mg, 0.19 mmol) [prepared as described in Example 17, Step 3] in acetonitrile (2 ml) at 0° C. The reaction mixture was allowed to warm to RT, ... | NCCCC[C@@H](NS(=O)(=O)N1CCN(c2ccc(Cl)cc2)CC1)C(=O)NO | null | 43.5 | null |
1,079,169 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | C(OC(=O)[NH:7][CH2:8][CH2:9][S:10]([C:13]1[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][C:19]=2[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=2)[CH:22]=1)(=[O:12])=[O:11])(C)(C)C.B(Br)(Br)Br.C(O)C>ClCCl>[NH2:7][CH2:8][CH2:9][S:10]([C:13]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)... | COc1ccc(-c2cc(S(=O)(=O)CCNC(=O)OC(C)(C)C)c3ccncc3c2)cc1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCO | null | null | null | null | null | null | null | null | null | 0 | null | To {2-[7-(4-methoxy-phenyl)-isoquinoline-5-sulfonyl]-ethyl}-carbamic acid tert-butyl ester (25.00 g, 56.49 mmol) in dichloromethane (1 L) at 0° C. add BBr3 (1.0 M in dichloromethane, 200 mL, 200 mmol) over 40 min with vigorous overhead stirring. Remove the cooling bath and stir at room temperature overnight. Cool to 0°... | NCCS(=O)(=O)c1cc(-c2ccc(O)cc2)cc2cnccc12 | null | 55.1 | null |
1,450,975 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1>C1COCC1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:12])[NH:28][C:25]2[S:26][CH:27]=[C:23]([S:22][CH3:21])[N:24]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2] | CSc1csc(N)n1 | CC(=O)Oc1ccc(C(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | null | Into a solution of 510 (0.815 g, 4.10 mmol) and dry THF (20.0 mL) was added a solution of triethylamine (0.572 mL, 4.10 mmol) and dry THF (5.00 mL), followed by a solution of 508 (0.500 g, 3.42 mmol) dissolved in dry THF (15.0 mL). The reaction was stirred at room temperature. After stirring overnight, the reaction was... | CSc1csc(NC(=O)c2ccc(OC(C)=O)cc2)n1 | null | 109 | null |
191,967 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | [CH3:1][O:2][CH2:3][CH:4]([OH:21])[C@@H:5]([NH:10]C(OCC1C=CC=CC=1)=O)[CH2:6][CH:7]([CH3:9])[CH3:8].[ClH:22]>CO.[Pd]>[ClH:22].[CH3:1][O:2][CH2:3][CH:4]([OH:21])[C@@H:5]([NH2:10])[CH2:6][CH:7]([CH3:9])[CH3:8] | COCC(O)[C@H](CC(C)C)NC(=O)OCc1ccccc1 | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 94 mg of the ether compound obtained in 10 ml of methanol was added 0.16 ml of a 2N-hydrochloric acid, and the mixture was hydrogenated over 10 mg of a 10% palladium charcoal under hydrogen atmosphere. After filtration of the catalyst, the filtrate was evaporated under reduced pressure to obtain 54 mg ... | COCC(O)[C@@H](N)CC(C)C | null | null | null |
245,693 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:24]1CCOCC1.C(OC(Cl)=O)C(C)C>O1CCCC1>[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:20]([NH2:24])=[O:22])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O... | O=C(N[C@@H](Cc1ccccc1)C(=O)O)OCc1ccccc1 | CN1CCOCC1 | null | CC(C)COC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.02 | An 18 g portion of Nα -[(phenylmethoxy)carbonyl]-L-phenylalanine and 6.6 ml of N-methylmorpholine were dissolved in 150 ml of tetrahydrofuran and stirred at 31 10° C. as 8.04 ml of isobutylchloroformate was added. After 1 minute, ammonia gas was bubbled through the mixture until it was saturated. The mixture was stirre... | NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1 | null | null | null |
393,006 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | Br[C:2]1[C:11]2[NH:10][C:9](=[O:12])[C:8](=[O:13])[NH:7][C:6]=2[C:5]2[CH2:14][CH:15]([NH:17][C:18](=[O:20])[CH3:19])[CH2:16][C:4]=2[CH:3]=1.C([O-])(=O)C.[K+]>CN(C)C=O.[Pd]>[O:13]=[C:8]1[NH:7][C:6]2[C:5]3[CH2:14][CH:15]([NH:17][C:18](=[O:20])[CH3:19])[CH2:16][C:4]=3[CH:3]=[CH:2][C:11]=2[NH:10][C:9]1=[O:12] | CC(=O)NC1Cc2cc(Br)c3[nH]c(=O)c(=O)[nH]c3c2C1 | null | null | [Pd] | CC(=O)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 0.12 | N-(5-Bromo-2,3-dioxo-2,3,4,7,8,9-hexahydro-1H-cyclopenta[f]quinoxalin-8-yl)-acetamide (1 g, 3 mmol) was dissolved in dimethylformamide (75 mL) and treated with potassium acetate (0.33 g) and 20% palladium on carbon (0.2 g) and shaken on a Parr apparatus under a hydrogen atmosphere (51 psi) for 7 min. The catalyst was r... | CC(=O)NC1Cc2ccc3[nH]c(=O)c(=O)[nH]c3c2C1 | null | 96.4 | null |
620,656 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([NH:14][CH2:15][CH2:16][OH:17])[N:3]=1.[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[OH:17][CH2:16][CH2:15][NH:14][C:4]1[N:5]=[C:6]([NH:10][CH2:11][CH2:12][OH:13]... | Oc1ccccc1N1CCNCC1 | N#Cc1c(Cl)nc(NCCO)nc1NCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in example 20b, 4-chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile was treated with 1-(2-hydroxy-phenyl)-piperazine in dioxane in the presence of N-ethyl-diisopropylamine at 60° C. to yield 2,4-bis-(2-hydroxy-ethylamino)-6-[4-(2-hydroxy-phenyl)-piperazin-1-yl]-pyrimi... | N#Cc1c(NCCO)nc(NCCO)nc1N1CCN(c2ccccc2O)CC1 | null | null | null |
1,741,901 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>[Cu].CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:18]=[CH... | c1ccc2c(c1)[nH]c1ccccc12 | Brc1cccc(Br)c1 | null | [Cu] | O=C([O-])[O-] | [K+] | 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 | 130 | null | (see Kido, J.; Su, S. -J.; Sasabe, H.; Takeda, T.; Chem. Mater. 2008, 20(5), 1691-1693, which is incorporated by reference herein for its relevant teachings) was prepared as follows: a mixture of carbazole (4.000 g, 23.92 mmol), 1,3-dibromobenzene (14.11 g, 59.81 mmol), K2CO3 (9.919 g, 71.77 mmol), copper powder (4.561... | Brc1cccc(-n2c3ccccc3c3ccccc32)c1 | null | 71 | null |
1,642,267 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][N:19]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:24][CH2:25][S:26](Cl)(=[O:28])=[O:27].O>C1COCC1>[CH:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[C:15]4=[N:20][S:26](=[O:28])(=[O:27])[CH2:25][CH2:24][N:1... | O=S(=O)(Cl)CCCl | Nc1nccnc1-c1ccc(OC2CCCCC2)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 80 | 3 | A mixture of 3-[4-(cyclohexyloxy)phenyl]pyrazin-2-amine (470 mg) in THF (dry) (25.00 mL) was added to a mixture of NaH (60%, 349 mg) and 2-chloroethanesulfonyl chloride (853 mg) in THF (dry) (25 mL) at room temperature. The mixture was stirred at room temperature overnight and 80° C. for 3 hr. Water was added and THF w... | O=S1(=O)CCN2C=CN=C(c3ccc(OC4CCCCC4)cc3)C2=N1 | null | 83.2 | null |
377,596 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | COC[O:4][CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][N:9]=[CH:8][C:7]=1Br.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[CH2:22][CH2:21][C:20]([N+:28]([O-:30])=[O:29])=[CH:19]2>>[CH3:27][O:26][C:25]1[CH:24]=[C:23]2[C:18](=[CH:17][C:16]=1[O:15][CH3:14])[C@@H:19]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH3... | COCOCc1c(C)cncc1Br | COc1cc2c(cc1OC)CCC([N+](=O)[O-])=C2 | null | null | null | null | null | null | null | 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 compound of step 14c was condensed with 1,2-dihydro-6,7-dimethoxy-3-nitronaphthalene according to the procedure of Example 13c. The protecting methoxymethyl group was removed from the intermediate by a standard hydrolysis method (HCl, ethanol). | COc1cc2c(cc1OC)[C@@H](c1cncc(C)c1CO)[C@H]([N+](=O)[O-])CC2 | null | null | null |
934,576 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:24][CH2:23][C@@H:19]3[CH2:20][NH:21][CH2:22][C@H:18]3[C@@H:17]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1C(=O)N([I:42])C(=O)C1>FC(F)(F)C(O)=O>[F:34][C:2]([F:1])([F:33])... | O=C1CCC(=O)N1I | Cc1cc(F)ccc1[C@@H]1[C@@H](O[C@H](C)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)OC[C@@H]2CNC[C@H]21 | 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 | A solution of (3aS,6R,7R,7aR)-6-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-7-(4-fluoro-2-methylphenyl)octahydropyrano[3,4-c]pyrrole (55.8 mg, 0.12 mmol) and NIS (53 mg, 0.23 mmol) in 2 mL trifluoroacetic acid was stirred at rt for 40 min. Volatiles were removed. The crude was purified by reverse phase HPLC to affo... | Cc1cc(F)c(I)cc1[C@@H]1[C@@H](O[C@H](C)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)OC[C@@H]2CNC[C@H]21 | null | null | null |
493,508 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | Cl[C:2](Cl)([O:4][C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.C(N([CH2:18][CH3:19])CC)C>>[C:5]([C:18]1([CH3:19])[CH2:7][O:6][C:5](=[O:11])[O:4][CH2:2]1)([O:4][CH3:2])=[O:6] | CCN(CC)CC | O=C(OC(Cl)(Cl)Cl)OC(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 | As set out hereinabove, the binder component of the dispersion of the invention is an organic polycarbonate polymer. The resulting polymer of the polymerization of 5-carbomethoxy-5-methyl-1,3-dioxan-2-one may be used as a component of the polymer binder. The polycarbonate polymer of 5-carbomethoxy-5-methyl-1,3-dioxan-2... | COC(=O)C1(C)COC(=O)OC1 | null | null | null |
1,539,171 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [NH2:1][C:2]1[C:3]([C:14]([NH2:16])=O)=[N:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[NH2:1][C:2]1[C:3]([C:14]#[N:16])=[N:4][CH:5]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1 | NC(=O)c1ncc(N2CCOCC2)cc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | CC#N | null | null | null | null | null | null | null | null | null | 25 | null | A stirred solution of 3-amino-5-morpholinopicolinamide (0.35 g, 1.57 mmol) in acetonitrile (10 mL) was treated with phosphorus oxychloride (0.29 mL, 3.15 mmol). The reaction was heated at reflux for 1 h. After this time the reaction was cooled to rt and evaporated in vacuo. The residue was dissolved in Et2O (10 mL) and... | N#Cc1ncc(N2CCOCC2)cc1N | null | null | null |
83,666 | ord_dataset-7bed824f566d4af0b51d74d386b14bd6 | null | 1981-01-01T00:07:00 | true | [Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[C:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH3:12])=[CH:4][CH:3]=1>C(O)C.[Pt].[H][H]>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH3:12])=[CH:4][CH:3]=1 | [H][H] | CN1CCCC1=Cc1ccc(Br)cc1 | null | [Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Hydrogenate 21.5 g of 2-(4-bromobenzylidene)-1-methylpyrrolidine in 400 ml of ethanol with platinum on activated charcoal/hydrogen. Filter out the catalyst, concentrate the filtrate and distil the residue to obtain 18.5 g (85% of theory) of the title compound (b.p. 70° at 0.001 mm of Hg). | CN1CCCC1Cc1ccc(Br)cc1 | null | null | null |
1,037,864 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].CS[C:18](SC)=[C:19]1[C:28](=[O:29])[C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:20]1=[O:34]>C1(C)C=CC=CC=1>[CH2:30]([N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][N:23]=2)[C... | COCOCc1csc(N)c1S(N)(=O)=O | CCCCN1C(=O)C(=C(SC)SC)C(=O)c2cccnc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | The product of Example 309G (110 mg, 0.43 mmol) and the product of Example 315B (140.6 mg, 0.43 mmol) were reacted in toluene (5 mL) at 100° C. for 3 hours. The reaction was concentrated under reduced pressure and the residue was purified by chromatography on silica gel using a Biotage-12 m column eluting with 1:99 met... | CCCCn1c(=O)c(C2=NS(=O)(=O)c3c(COCOC)csc3N2)c(O)c2cccnc21 | null | 55.4 | null |
599,433 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [NH2:1][C:2]1[N:7]=[C:6](S(C)=O)[C:5]([C:11]#[N:12])=[C:4]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]([C:11]#[N:12])=[C:4]([C:13]2[S:14]... | CS(=O)c1nc(N)nc(-c2cccs2)c1C#N | NCCN1CCOCC1 | 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 | From 2-amino-4-methanesulfinyl-6-thiophen-2-yl-pyrimidine-5-carbonitrile and 4-(2-aminoethyl)morpholine in dioxane. ES-MS m/e (%): 331 (M+H+, 100). | N#Cc1c(NCCN2CCOCC2)nc(N)nc1-c1cccs1 | null | null | null |
1,142,394 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [I:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.C(OCC)(=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([O:10][C:5]2[CH:4]=[CH:3... | O=Cc1cc(I)ccc1O | Cc1ccc(S(=O)(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 60 | null | To a solution of 5-iodosalicylaldehyde (3 g, 12.1 mmol) (Aldrich) in N,N-dimethylformamide (20 mL) was added anhydrous K2CO3 (5 g, 36.3 mmol), and 4-(toluene-4-sulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester (5.4 g, 18.1 mmol, ASTATECH). The reaction mixture was heated at 60° C. for 18 h. The mixture was coo... | CC(C)(C)OC(=O)N1CCC(Oc2ccc(I)cc2C=O)CC1 | null | 83.9 | null |
1,071,473 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35]>C(Cl)Cl>[CH2:37]([O:36][C:34](=[O:35])[NH:1][C:2]1[CH:3]=... | Cc1ccc(N)cc1C(=O)c1ccc(Nc2ccc(F)cc2F)cc1Cl | C=CCOC(=O)Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 48 | Compound 494 (0.06 g, 0.16 mmol) was suspended in dry CH2Cl2 (1.5 mL) under an argon atmosphere in a screw cap vessel. K2CO3 (0.044 g, 0.32 mmol) was added followed by allyl chloroformate (0.034 mL, 0.032 mmol). The suspension was stirred for 48 h at room temperature. Work up as described in the preparation of compound... | C=CCOC(=O)Nc1ccc(C)c(C(=O)c2ccc(Nc3ccc(F)cc3F)cc2Cl)c1 | null | null | null |
1,067,475 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=[O:40]>>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([... | Cc1c(C)c2c(c(C)c1O)CCC(C)(C(=O)O)O2 | NCCCN1CCCC1=O | null | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | 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 amide coupling procedure described in protocol A, 499 mg 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (2.00 mmol), 357 mg CDI (2.2 mmol) and 569 mg 1-(3-aminopropyl)pyrrolidin-2-one (4.0 mmol) yielded 598 mg of 6-hydroxy-2,5,7,8-tetramethyl-N-(3-(2-oxopyrrolidin-1-yl)propyl)chroman-2-carboxamide... | Cc1c(C)c2c(c(C)c1O)CCC(C)(C(=O)NCCCN1CCCC1=O)O2 | null | 79.8 | null |
654,912 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | [CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:9]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[CH2:1]([NH:8][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7] | O=C1CCCCCO1 | CCCCCCCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | 3 | A mixture of n-heptylamine (1.21 g, 10.5 mmols) and 6-hexanolactone (1.14 g, 10 mmols) was stirred at 100° C. for 3 hours, and then crystallized from ether-hexane to obtain 1.77 g (yield 78%) of N-heptyl-6-hydroxyhexaneamide as colorless crystal. | CCCCCCCNC(=O)CCCCCO | null | 77.2 | null |
952,030 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | N[CH:2]1[CH2:6][C@@:5]([CH:26]([CH3:28])[CH3:27])([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=2[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:8])[CH:4]=[CH:3]1.[O:29]=C(C(OCC)=O)C(OCC)=O.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[C:22]([O:21][C:12]1[CH:13]=[CH:14][C:15]([C:17]([F:20... | CC(C)[C@]1(C(=O)NCc2cc(C(F)(F)F)ccc2OC(C)(C)C)C=CC(N)C1 | CCOC(=O)C(=O)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | 0 | 1 | A mixture of (1S)-4-amino-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]1-isopropylcyclopent-2-ene-1-carboxamide (35 g, 88 mmol) and diethyl oxomalonate (31 g, 176 mmol) in toluene (350 mL) was refluxed until no more starting material left as judged by HPLC. The reaction mixture was cooled to 0° C. and 1,8-diazabicyclo[5.... | CC(C)[C@]1(C(=O)NCc2cc(C(F)(F)F)ccc2OC(C)(C)C)C=CC(=O)C1 | null | 91.5 | null |
793,637 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([F:38])=[C:28](B2OCC(C)(C)CO2)[CH:29]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([F:38])=[C:26]([C:2]2[CH:3]=[C:4]([C:9]3[N:13]4[CH:1... | CC1(C)COB(c2cc(Cl)ccc2F)OC1 | CC(C)(O)c1ccn2c(-c3ccc(F)c(Cl)c3)cnc2c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 2-(5-chloro-2-fluorophenyl)-5,5-dimethyl-[1,3,2]dioxaborinane were coupled in the same way as in Example 30 to give 2-[3-(5′-chloro-2,2′-difluorobiphenyl-5-yl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]propan-2-ol as an off-white solid (6 mg, 3... | CC(C)(O)c1ccn2c(-c3ccc(F)c(-c4cc(Cl)ccc4F)c3)cnc2c1F | null | 3 | null |
1,518,012 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | Br[C:2]1[C:3]([CH2:8][CH2:9][CH:10]=[CH2:11])=[N:4][CH:5]=[CH:6][CH:7]=1.[B:12](OC(C)C)([O:17]C(C)C)[O:13]C(C)C.[Li]CCCC>C1(C)C=CC=CC=1.C1COCC1>[CH2:8]([C:3]1[C:2]([B:12]([OH:17])[OH:13])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH2:9][CH:10]=[CH2:11] | CC(C)OB(OC(C)C)OC(C)C | C=CCCc1ncccc1Br | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | -78 | 2 | To a stirring solution of 3-bromo-2-(but-3-en-1-yl)pyridine (Ref. Zhang, Z; Dwoskin, L. and Crooks, P. Tetrahedron Lett. 2011, 52, 2667-2669, 550 mg, 2.59 mmol) and triisopropyl borate (0.775 mL, 3.37 mmol) in toluene (4 mL) and THF (1 mL) cooled to −78° C. was added 2.5 M n-BuLi (1.349 mL, 3.37 mmol) over the course o... | C=CCCc1ncccc1B(O)O | null | 98.2 | null |
1,592,761 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | Cl[C:2]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:3]=1[O:4][C@@H:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].[Cl:16]C1C=CC(O)=CC=1C>>[Cl:16][C:13]1[CH:14]=[CH:2][C:3]([O:4][C@@H:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7])=[CH:11][C:12]=1[CH3:15] | Cc1cc(O)ccc1Cl | COC(=O)[C@H](C)Oc1cc(C)ccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following the same general protocol as described for the synthesis of the (S)-methyl 2-(2-chloro-5-methylphenoxy)propanoate (Step 1, Example 55), using the 4-chloro-3-methylphenol instead of the 2-chloro-5-methylphenol. | COC(=O)[C@H](C)Oc1ccc(Cl)c(C)c1 | null | null | null |
1,008,689 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14].[C:22]([NH:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)(=[O:24])[CH3:23]>>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[CH2:3][CH2:2][O... | CC(=O)Nc1ccc(O)cc1 | N#Cc1ccc(N(CCO)CC(F)(F)F)c(C(F)(F)F)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized as described in Example 1C from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-3-(trifluoromethyl)benzonitrile and 4-acetamidophenol: MS (APCI) m/z 446 (M+1). | CC(=O)Nc1ccc(OCCN(CC(F)(F)F)c2ccc(C#N)cc2C(F)(F)F)cc1 | null | null | null |
521,063 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[O:27]1[CH:32]2[CH:28]1[CH2:29][O:30][CH2:31]2>CN(C)C=O>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C... | COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)cc1O | C1OCC2OC12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 120 | null | 400 mg (1.2 mmol) of N-(3,5-dichloropyridin-4-yl)-3-hydroxy-4-methoxybenzamide (starting compound A16) and 540 mg (3.85 mmol) of potassium carbonate are stirred under a nitrogen atmosphere at RT for 1 h in 5 ml of dimethylformamide. The mixture is heated to 120° C. and 115 mg (1.3 mmol) of 3,4-epoxytetrahydrofuran are ... | COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)cc1OC1COCC1O | null | 27.1 | null |
660,307 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | [CH3:1][NH:2]C[C@H](C1C=CC=CN=1)O.Cl[CH2:13][C:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15]>>[CH3:1][NH:2][CH2:13][C@H:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[OH:15] | O=C(CCl)c1cccnc1 | CNC[C@@H](O)c1ccccn1 | null | null | null | null | null | null | null | 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 the preparation of (1R)-2-(methylamino)-1-pyridin-2-ylethanol (Preparations 68-69), 3-chloroacetylpyridine (Chem. Ber. 1951, 84, 147-149) is converted to the title compound, isolated as a pale yellow amorphous solid. | CNC[C@@H](O)c1cccnc1 | null | null | null |
1,140,723 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]3[S:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[C:20]([C:34]([F:37])([F:36])[F:35])[CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.[ClH:39]>C(O)C>[ClH:39].[NH2:7][C:8]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:2... | Cc1ccc(CCCOc2ccc(CCC3(NC(=O)OC(C)(C)C)COC(C)(C)OC3)cc2C(F)(F)F)s1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | 2 | Compound 48-4 (710 mg) was dissolved in ethanol (15 ml), concentrated hydrochloric acid (1.5 ml) was added, and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was concentrated, and the residue was washed with diethyl ether to give a white powder. The white powder was purified by HPLC, the obtained res... | Cc1ccc(CCCOc2ccc(CCC(N)(CO)CO)cc2C(F)(F)F)s1 | null | null | null |
443,500 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.[H-].[Na+].[N:18]1([C:23]2[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=2)[CH:22]=[CH:21][N:20]=[CH:19]1.O>C1COCC1>[N:18]1([C:23]2[CH:30]=[CH:29][C:26]([CH:27]=[CH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)[CH:22]=[CH:21][N:... | O=Cc1ccc(-n2ccnc2)cc1 | CCOP(=O)(Cc1ccccc1)OCC | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 48 | 1.0 g of diethylbenzylphosphonate were dissolved in 50 ml of dry THF under nitrogen gas flow. To this solution, were added 0.21 g of 60% NaH while cooling the solution with ice, and the resultant solution was then stirred for 2 hours at room temperature. After cooling the whole solution with ice, 0.75 g of 4-(imidazole... | C(=Cc1ccc(-n2ccnc2)cc1)c1ccccc1 | null | 46.6 | null |
1,297,123 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH2:1]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:2].[CH2:20](O)[CH2:21][CH2:22][OH:23]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([C:6]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:23][CH2:22][CH2:21]... | CCc1cc(C(=O)c2ccccc2)ccc1[N+](=O)[O-] | OCCCO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | null | A suspension of 3-ethyl-4-nitro-benzophenone (11f) (20.0 g, 78.4 mmol), 1,3-propandiol (7.15 g, 94.0 mmol), p-toluenesulfonic acid monohydrate (50 mg) in toluene (300 mL) was refluxed using a Dean-Stark-trap for 24 hours. The Dean-Stark-trap was then replaced by a Soxhlet-extractor filled with molecular sieve and the m... | CCc1cc(C2(c3ccccc3)OCCCO2)ccc1[N+](=O)[O-] | null | 91.8 | null |
1,405,687 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [F:1][C:2]1[C:7]([C:8]([C:10]2[C:18]3[C:17](O)=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[O:9])=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)(=[O:24])=[O:23].P(Cl)(Cl)([Cl:36])=O>>[Cl:36][C:17]1[C:18]2[C:10]([C:8]([C:7]3[C:2]([F:1])=[C:3]([NH... | CCCc1ccc(S(=O)(=O)Nc2ccc(F)c(C(=O)c3c[nH]c4ncnc(O)c34)c2F)cc1 | 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 | 100 | null | To N-[2,4-difluoro-3-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-4-propyl-benzenesulfonamide (P-1030, 239 mg, 0.506 mmol), phosphoryl chloride (4.0 mL, 43 mmol) is added and the suspension is heated in an oil bath at 100° C. for one hour. The reaction is allowed to cool, then poured onto ice. The resulti... | CCCc1ccc(S(=O)(=O)Nc2ccc(F)c(C(=O)c3c[nH]c4ncnc(Cl)c34)c2F)cc1 | null | 87.8 | null |
783,068 | ord_dataset-8034115bd2ec4d3e95bd3ff7cfde0bde | null | 2007-01-01T00:07:00 | true | C([O:8][CH2:9][C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C:14]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=4)[C:15]=3[CH:16]=2)[N:11]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][CH2:9][C:10]1[NH:19][C:18](=[O:20])[C:17]2[C:12](=[CH:13][C... | CC(C)(C)OC(=O)c1ccc(NC2CCc3cc4nc(COCc5ccccc5)[nH]c(=O)c4cc32)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 45 | 3 | To a solution of tert-butyl 4-{N-[(6RS)-2-benzyloxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino}benzoate (1.40 g, 2.8 mmol) in EtOH (150 ml) was added 10% Pd/C (0.665 g). The mixture was stirred at 45° C. for 3 h, then more catalyst (0.200 g) was added and stirring was continued at 50° C. for 6... | CC(C)(C)OC(=O)c1ccc(NC2CCc3cc4nc(CO)[nH]c(=O)c4cc32)cc1 | null | 59.5 | null |
233,549 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Cu][C:18]#[N:19]>CN1CCCC1>[N:12]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:18]#[N:19])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH3:11])[CH:16]=[CH:15][N:14]=[CH:13]1 | CCCC(c1ccc(Br)cc1)n1ccnc1 | N#C[Cu] | null | CN1CCCC1 | null | null | null | 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 | 2.79 g of 1-[1-(4-bromophenyl)-butyl]-imidazole and 1.8 g of copper(I) cyanide are heated in 5 ml of N-methylpyrrolidine for 4 hours at 180° C. under a protecting gas atmosphere (argon). After cooling, it is precipitated in 50 ml of ammonia solution, stirred for 15 more minutes at room temperature and extracted with et... | CCCC(c1ccc(C#N)cc1)n1ccnc1 | null | 68.4 | null |
12,461 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH:10]=[CH:11][C:12]4=[O:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]4=[O:21])[C:8]=3[CH2:7][CH2:6][... | COc1ccc2c(c1)CCC1=C2CC[C@]2(C)C(=O)C=C[C@@H]12 | [H][H] | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 0.5 g. of 3-methoxy-14α-estra-1,3,5(10), 8,15-pentaen-17-one in 25 ml. of ethanol is reduced catalytically with 50 mg. of 5% palladium-on-charcoal until a molar equivalent of hydrogen is taken up. The catalyst is filtered off and the filtrate evaporated to dryness to yield the known 3-methoxyestra-1,3,5 (10),8-tetraen-... | COc1ccc2c(c1)CCC1=C2CC[C@]2(C)C(=O)CC[C@@H]12 | null | null | null |
884,880 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]1.[C:18]1([N:24]2[C:28]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[CH:27][C:26]([CH:34]=O)=[N:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]... | O=Cc1cc(-c2ccco2)n(-c2ccccc2)n1 | Cc1cccc(N2CCN(CCN)CC2)c1C | null | null | null | null | null | null | null | 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 19 was prepared using the same method as that of Example 1 except that 4-(2,3-dimethylphenyl)piperazin-1-ylethylamine and 1-phenyl-5-(2-furyl)pyrazole-3-carbaldehyde were used. | Cc1cccc(N2CCN(CCNCc3cc(-c4ccco4)n(-c4ccccc4)n3)CC2)c1C | null | 77.9 | null |
1,533,987 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[N:5]=[CH:4][N:3]=1.[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:22]([C:25]1[N:29]=... | CC(C)c1noc(C2CCNCC2)n1 | CC(=O)c1c(Cl)ncnc1Oc1ccc(S(C)(=O)=O)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1-[4-chloro-6-(4-methanesulfonyl-phenoxy)-pyrimidin-5-yl]-ethanone (0.21 mmol, 70 mg) and 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine (0.21 mmol, 49 mg) in N,N-dimethyl formamide (500 uL) was added potassium carbonate (0.21 mmol, 29 mg). The mixture was microwaved at 100° C. for 150 seconds. Its p... | CC(=O)c1c(Oc2ccc(S(C)(=O)=O)cc2)ncnc1N1CCC(c2nc(C(C)C)no2)CC1 | null | 19.6 | null |
297,875 | ord_dataset-b6309a86b70f4ca08fd301828cacf950 | null | 1994-01-01T00:10:00 | true | C([Mg]Br)C.[CH2:5]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:21]([O:23]CC)C>>[OH:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:19][C:18]=1[CH:21]=[O:23] | CCCCCCCCCc1ccc(O)cc1 | CCOCC | null | CC[Mg]Br | null | null | null | 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 | 0.5 | Ethylmagnesium bromide (18 ml of 3M solution in diethyl ether) was added dropwise to a stirred solution of 4-nonylphenol (11.2 g) in diethyl ether (100 ml) at 0°-10° C. under nitrogen. Stirring was continued at 10° C. for 30 minutes, the mixture was allowed to warm to ambient temperature, the bulk of the diethyl ether ... | CCCCCCCCCc1ccc(O)c(C=O)c1 | null | null | null |
325,226 | ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22 | null | 1996-01-01T00:02:00 | true | Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=[O:4].[C:11](#[N:15])[CH2:12][C:13]#[N:14].CC(C)([O-])C.[K+]>O1CCCC1>[Cl:10][C:7]1[S:6][C:5]([C:3]([CH2:2][CH:12]([C:11]#[N:15])[C:13]#[N:14])=[O:4])=[CH:9][CH:8]=1 | O=C(CBr)c1ccc(Cl)s1 | N#CCC#N | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-bromo-1-(5-chloro-2-thienyl)ethanone (11.50 g, 48 mmol) in tetrahydrofuran is added to a solution of malononitrile (3.17 g, 48 mmol) and potassium tert-butoxide (5.70 g, 51 mmol) in tetrahydrofuran at 0° C. The reaction mixture is stirred for several minutes, concentrated in vacuo, diluted with water an... | N#CC(C#N)CC(=O)c1ccc(Cl)s1 | null | null | null |
8,819 | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | null | 1976-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][S:8][C:9]2[C:10]([C:15]([O:17]C)=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[C:10]([C:15]([OH:17])=[O:16])=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:19][CH:20]=1 | COC(=O)c1ncccc1SCc1ccc(OC)cc1 | 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 | To a solution of 3 g. of methyl 3-(p-methoxybenzylthio)picolinate in 50 ml. of ethanol is added 10 ml. of 20% aqueous sodium hydroxide solution and the mixture is warmed on a steam bath for two hours. The alcohol is evaporated off and the residue is cooled and acidified with dilute hydrochloric acid. The precipitate is... | COc1ccc(CSc2cccnc2C(=O)O)cc1 | null | null | null |
760,985 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][CH:14]=1.N1CCCCC1>C1C=CC=CC=1>[CH2:26]([O:25][C:23]([C:22]([C:21](=[O:28])[CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([F:12])... | CCOC(=O)CC(=O)CCc1ccc(F)cc1 | O=Cc1ccc(C(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | A mixture of 4-carboxybenzaldehyde (2.07 g, 13.81 mmol), ethyl 5-(4-fluorophenyl)-3-oxopentanoate (3.29 g, 13.81 mmol) and piperidine (0.25 mL, 2.53 mmol) in benzene (60 mL) was heated at reflux overnight under Dean-Stark conditions. The reaction mixture was concentrated and the crude material was dissolved in EtOAc. T... | CCOC(=O)C(=Cc1ccc(C(=O)O)cc1)C(=O)CCc1ccc(F)cc1 | null | 25.4 | null |
455,522 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | C(=O)([O-])[O-].[Na+].[Na+].Br[CH:8](Br)[C:9]([C:11]([F:14])([F:13])[F:12])=O.[NH2:16][CH:17]([C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([Cl:29])=[CH:23][C:22]=1[Cl:30])[C:18]([NH2:20])=[O:19].Cl>O>[Cl:30][C:22]1[CH:23]=[C:24]([Cl:29])[C:25]([O:27][CH3:28])=[CH:26][C:21]=1[C:17]1[C:18](=[O:19])[NH:20][C:9]([C:11]([F:1... | O=C(C(Br)Br)C(F)(F)F | COc1cc(C(N)C(N)=O)c(Cl)cc1Cl | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a mixed solution of 16.7 g of sodium carbonate and 60 ml of water was added dropwise 10.6 g of 1,1-dibromo-3,3,3-trifluoroacetone at such a rate that the temperature of the reaction mixture became not higher than 55° C. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 min... | COc1cc(-c2ncc(C(F)(F)F)[nH]c2=O)c(Cl)cc1Cl | null | null | null |
745,518 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | C(OC(N1CCC(NC([N:16]2[CH2:21][CH2:20][N:19]3[C:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:23]([Cl:28])[C:24]([C:25](=[O:27])[NH2:26])=[C:18]3[CH2:17]2)=O)CC1)=O)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>ClCCl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[Cl:28][C:23]1[C:24]([C:25]([NH2:2... | CC(C)OC(=O)N1CCC(NC(=O)N2CCn3c(c(C(N)=O)c(Cl)c3-c3ccccc3)C2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | A solution of 8-carbamoyl-7-chloro-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (2.75 g, Reference Example 2) in dichloromethane (60 mL) was treated with trifluoroacetic acid (5.64 mL). After stirring at room temperature for a further 3 hours the reaction mixture was further treated... | NC(=O)c1c(Cl)c(-c2ccccc2)n2c1CNCC2 | null | null | null |
949,420 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]4[N:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])=[CH:16][CH:15]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:33].[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=... | Cc1cc(C(=O)Nc2ccc(C(=O)c3ccc4c(c3)NC(=O)C4=CO)cc2)n(C(C)(C)C)n1 | CN1CCN(c2ccc(N)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 65 | 24 | A small screw cap test tube was charged with 2-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 65, 100 mg, 0.225 mmol) and THF (2 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (47 mg... | Cc1cc(C(=O)Nc2ccc(C(=O)c3ccc4c(c3)NC(=O)C4=CNc3ccc(N4CCN(C)CC4)cc3)cc2)n(C(C)(C)C)n1 | null | 42.4 | null |
1,136,251 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=1[CH3:25])(=[O:15])=[O:14])(=O)=O.[I-:26].[Na+]>CC(C)=O>[I:26][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=1[... | COc1cc(C)c(S(=O)(=O)N2CCCCC2COS(C)(=O)=O)c(C)c1 | [I-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 120 | null | (1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methyl methanesulfonate (0.25 g, 0.639 mmol) and sodium iodide (0.383 g, 2.554 mmol) were dissolved in acetone (7 ml) and the solution was heated at 120° C. in a microwave oven (CEM Discover; 100 watt) for 1 h. The solvent was removed in vacuo, the residue was dis... | COc1cc(C)c(S(=O)(=O)N2CCCCC2CI)c(C)c1 | null | null | null |
101,191 | ord_dataset-d06b137b66b3478fb6a0d41a5efd32f8 | null | 1982-01-01T00:12:00 | true | [Cl:1][C:2]1[C:7](OC2C=CC=CC=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH3:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH2:25] | O=[N+]([O-])c1ccc(Oc2ccccc2)c(Cl)c1Oc1ccccc1 | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 120 | null | 68.3 gm of 2-chloro-4-nitro-1,3-diphenoxy-benzene were dissolved in 300 ml of toluene, and the solution was admixed with 100 ml of concentrated aqueous ammonia in an autoclave. The autoclave was then closed, the internal pressure was increased to 3 bar with gaseous ammonia, and the contents were heated for 12 hours at ... | Nc1c([N+](=O)[O-])ccc(Oc2ccccc2)c1Cl | null | 98 | null |
768,148 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:29])([C:23]2[N:27]([CH3:28])[CH:26]=[N:25][CH:24]=2)[C:10](O[C@@H]2C[C@H](C)CC[C@H]2C(C)C)=[O:11])=[CH:5][CH:4]=1)#[N:2].[Li+].[BH4-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[OH:29][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([C:23]1[N:27]([CH3:28])[CH:26]=[N:25][CH:... | CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C(O)(c1ccc(C#N)cc1)c1cncn1C | null | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [BH4-] | [Li+] | 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 | 55 | 2 | A mixture of Example 93B (2.15 g, 78% potency, 4.24 mmol) in THF (6.5 mL) was treated with a solution of 2M LiBH4 in THF (3.3 mL, 6.1 mmol), heated to 55° C. for 3 hours, cooled to room temperature, treated with 20% citric acid (12 mL), warmed to 50° C. for 30 minutes, and extracted with MTBE (2×20 mL). The aqueous pha... | Cn1cncc1C(O)(CO)c1ccc(C#N)cc1 | null | null | null |
371,273 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH:25][CH2:26][C@H:27]([OH:31])[C:28]([OH:30])=[O:29])=[O:24])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH:... | CC(C)(C)OC(=O)N1CCC(CCOc2ccc(C(=O)NC[C@H](O)C(=O)O)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | A solution of 17-3 (45 mg, 0.10 mmol), TFA (1 mL), and CH2Cl2 (1 mL) was stirred at ambient temperature for 1.0 h. Concentration and flash chromatography (silica, 10:1:1 ethanol H2O/NH4OH) gave 17-4 (28 mg) as a white solid. Rf 0.17 (10:1:1 ethanol) H2O/NH4OH). | O=C(NC[C@H](O)C(=O)O)c1ccc(OCCC2CCNCC2)cc1 | null | 83.2 | null |
320,810 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | [CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=2[CH:4]2[CH2:12][CH2:13][CH:14]([NH:15]CC3C=CC=CC=3)[CH:3]12>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:15][CH:14]1[CH:3]2[N:2]([CH3:1])[C:10]3[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=3[CH:4]2[CH2:12][CH2:13]1 | CN1c2ccc(O)cc2C2CCC(NCc3ccccc3)C21 | null | null | [Pd+2] | [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 | 20% Palladium hydroxide on carbon (1.4 g) was added to a solution of 1,2,3,3a,4,8b-hexahydro-4-methyl-3-phenylmethylaminocyclopent[b]indol-7-ol (14 grams) in ethanol (100 ml) and the mixture was hydrogenated at 45 psi H2 pressure using a Parr apparatus at 50° C. for 5 hours. The mixture was filtered and the solution wa... | CN1c2ccc(O)cc2C2CCC(N)C21 | null | 110.1 | null |
460,438 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | C([O:4][CH2:5][C:6]1[C:11]([Cl:12])=[C:10]([N:13]([CH2:15][CH2:16][Cl:17])[CH3:14])[CH:9]=[CH:8][N:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:12][C:11]1[C:6]([CH2:5][OH:4])=[N:7][CH:8]=[CH:9][C:10]=1[N:13]([CH2:15][CH2:16][Cl:17])[CH3:14] | CC(=O)OCc1nccc(N(C)CCCl)c1Cl | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | 1.83 g of 3-chloro-4-[(2-chloroethyl)-methylamino]-pyridin-2-ylmethyl acetate and 250 mg of potassium carbonate in 20 ml of methanol are stirred at room temperature for 8 h. The mixture is then filtered and the filtrate is concentrated. The residue is triturated with diethyl ether. 1.43 g (92%) of the title compound ar... | CN(CCCl)c1ccnc(CO)c1Cl | null | 92.1 | null |
646,814 | ord_dataset-5d77a731aa10488794c824ad12021f57 | null | 2004-01-01T00:09:00 | true | COC1C=C(C=CC=1OC)C[NH:7][C:8]1[N:9]=[C:10]([C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:18])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1.C(O)(C(F)(F)F)=O>>[NH2:7][C:8]1[N:9]=[C:10]([C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[O:18])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1 | COc1ccc(CNc2nc(C(=O)c3cccs3)c3sccc3n2)cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-[N-(3,4-dimethoxybenzyl)]aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.06 g, 0.15 mmol) and TFA (2 mL) was refluxed for 2 h, cooled, concentrated in vacuo to half its original volume, diluted with CH2Cl2 (50 mL), washed with saturated sodium bicarbonate solution (3×25 mL) then brine (25 mL), dri... | Nc1nc(C(=O)c2cccs2)c2sccc2n1 | null | 102 | null |
1,475,491 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH2:26][CH2:27][O:28]C6CCCCO6)[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:42])C(=O)C1.O1CCOCC1>C(Cl)Cl.Cl>[Br:42][C:3]1[N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[... | CC(c1ccc2nccn2c1)c1cnc2ccc(-c3cnn(CCOC4CCCCO4)c3)nn12 | O=C1CCC(=O)N1Br | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 3 | (rac)-3-(1-Imidazo[1,2-a]pyridin-6-yl-ethyl)-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine (obtained by analogy of Stage 185.1 by replacing (rac)-6-chloro-3-[1-(3-methyl-3H-benzoimidazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine with (rac)-6-chloro-3-(1-imidazo[1,2-a]pyridin-6-yl-ethyl... | CC(c1ccc2ncc(Br)n2c1)c1cnc2ccc(-c3cnn(CCO)c3)nn12 | null | null | null |
905,330 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH:1]1([N:4]2[C:8]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[N:7][N:6]=[C:5]2[CH2:15]O)[CH2:3][CH2:2]1.[CH2:17]([O:19][C:20](=[O:31])[CH:21](P(OCC)(OCC)=O)[CH3:22])[CH3:18].C1CCN2C(=NCCC2)CC1>C(#N)C.O=[Mn]=O>[CH2:17]([O:19][C:20](=[O:31])[C:21]([CH3:22])=[CH:15][C:5]1[N:4]([CH:1]2[CH2:2][CH2:3]2)[C:8]([C:9]2[CH:1... | CCOC(=O)C(C)P(=O)(OCC)OCC | OCc1nnc(-c2ccncc2)n1C1CC1 | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | CC#N | null | null | null | null | null | null | null | null | null | 80 | null | (4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanol (6.8 g, 31.4 mmol) was mixed with MnO2 (40 g, 0.46 mol) in acetonitrile at r.t. for 2 hours and then heated at 80° C. for another 30 min. The reaction mixture was filtered through celite. The filtrate was mixed with 2-(diethoxy-phosphoryl)-propionic acid et... | CCOC(=O)C(C)=Cc1nnc(-c2ccncc2)n1C1CC1 | null | null | null |
1,020,565 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | [NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:22][N:19]([CH2:20][CH2:21]2)[CH2:18][CH:17]=[CH:16]3)=[CH:11][N:10]=1>CN(C)C=O>[N:1]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]34[CH2:22][N:19]([CH2:20][CH2:21]3)[CH2:18][CH:17]=[CH:16]4)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1 | c1c[nH]cn1 | Brc1ccc(C23C=CCN(CC2)C3)cn1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 0.64 g (9.42 mmol) of imidazole dissolved in 3 ml of dimethylformamide is introduced into a 10 ml three-necked round-bottomed flask. 0.415 g (10.4 mmol) of sodium hydride as a 60% dispersion in oil is then added and the mixture is stirred at room temperature for 1 hour. The mixture is then added to a solution of 5-(2-b... | C1=CC2(c3ccc(-n4ccnc4)nc3)CCN(C1)C2 | null | 49.3 | null |
978,619 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH3:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][C:21]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P... | Cc1ccc(C(N)=O)cc1B1OC(C)(C)C(C)(C)O1 | O=C1CN(c2nncc3cc(Br)ccc23)CCN1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | COCCOC | null | null | null | null | null | null | null | null | null | 90 | 1 | A mixture of 4-(6-bromophthalazin-1-yl)piperazin-2-one (0.1 g, 0.3 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.09 g, 0.3 mmol), and tetrakis(triphenylphosphine)palladium (0.02 g, 0.02 mmol) in 5 mL DME/EtOH (4:1) was treated with 2M potassium carbonate (0.5 mL, 1.0 mmol). The mixture res... | Cc1ccc(C(N)=O)cc1-c1ccc2c(N3CCNC(=O)C3)nncc2c1 | null | 55.3 | null |
1,004,988 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:5]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:36])(=[N:27][C:28](=[O:35])[NH:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:26])=[CH:21][CH:20]=1>>[CH:30]1([NH:29][C:28]([N:27]=[S:25]([C:22]2[CH:21... | CS(=O)(=NC(=O)NC1CCCC1)c1ccc(N)cc1 | C[C@H](CO)Nc1nc(Cl)ncc1-c1cccs1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In the reaction of (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)propan-1-ol (103.4 mg, 0.38 mmol) with (RS)—S-(4-aminophenyl)-N-(cyclopentylcarbamoyl)-S-methylsulphoximide (98 mg, 0.35 mmol) according to procedure 5c, the desired product is obtained in 18% yield (33 mg) after chromatographic purification (silica g... | C[C@H](CO)Nc1nc(Nc2ccc(S(C)(=O)=NC(=O)NC3CCCC3)cc2)ncc1-c1cccs1 | null | 18 | null |
1,733,950 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Na].[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[C:5](Cl)[N:4]=1.[Na+].[Cl-].[CH2:13]([OH:17])[CH:14]([CH3:16])[CH3:15]>>[CH3:15][CH:14]([CH3:16])[CH2:13][O:17][C:5]1[N:4]=[C:3]([NH2:2])[N:8]=[C:7]([NH2:9])[CH:6]=1 | CC(C)CO | Nc1cc(Cl)nc(N)n1 | null | [Cl-] | [Na+] | [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 | 10 | To a solution of 6.9 g (0.30 mol) sodium in 185 ml isobutyl alcohol were added 43.4 g (0.30 mol) 2,4-diamino-6-chloropyrimidine. The mixture was heated under reflux with stirring for 10 h. The reaction mixture was then stirred at 80° C. for a further 36 h. After the reaction was ended the precipitated NaCl was separate... | CC(C)COc1cc(N)nc(N)n1 | null | 75 | null |
1,509,332 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [F:1][C:2]1([F:44])[CH2:7][CH2:6][CH2:5][C@H:4]([O:8][C:9]2[C:14]([F:15])=[CH:13][C:12]([S:16]([N:19](CC3C=CC(OC)=CC=3OC)[C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)(=[O:18])=[O:17])=[C:11]([F:37])[CH:10]=2)[C@H:3]1[C:38]1[N:42]([CH3:43])[N:41]=[CH:40][CH:39]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:44][C:2]1([F:1])[... | COc1ccc(CN(c2ccncn2)S(=O)(=O)c2cc(F)c(O[C@H]3CCCC(F)(F)[C@@H]3c3ccnn3C)cc2F)c(OC)c1 | null | null | CC[SiH](CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the 4-{[(1S*,2R*)-3,3-difluoro-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (260 mg, 0.398 mmol) prepared in Example 117e, triethylsilane (0.20 mL), triflu... | Cn1nccc1[C@@H]1[C@@H](Oc2cc(F)c(S(=O)(=O)Nc3ccncn3)cc2F)CCCC1(F)F | null | 114.4 | null |
422,900 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>C(Cl)Cl.CCOCC>[CH3:29][O:28][N:27]([CH3:26])[C:10](=[O:12])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1 | CNOC | CSc1ccc(CC(=O)O)cc1 | null | Cl | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCOCC | null | null | null | null | null | null | null | null | null | 25 | 0.33 | To a solution of 4-(methylthio)phenylacetic acid (18.3 g, 0.100 mol) in methylene chloride (200 mL) was added 1,1'-carbonyldiimidazole (16.3 g, 0.100 mol) portionwise. The mixture was stirred at room temperature for 20 minutes, and N,O-dimethylhydroxylamine hydrochloride (9.8 g, 0.100 mol) was added. The reaction mixtu... | CON(C)C(=O)Cc1ccc(SC)cc1 | null | 92.8 | null |
158,390 | ord_dataset-58ec6779628e43e2b3f0972725f262e6 | null | 1987-01-01T00:05:00 | true | [N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH3:10][C:11]1([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:20]>>[CH3:10][C:11]1([CH3:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:1]([O-:4])=[O:2])[CH:18]=2)[NH:13][C:12]1=[O:20] | CC1(C)C(=O)Nc2ccccc21 | O=[N+]([O-])O | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of 22 ml. fuming nitric acid in 200 ml. 80% sulphuric acid is added dropwise, with cooling, to a solution of 100 g. (0.62 mol) 3,3-dimethylindolin-2-one in 500 ml. 80% sulphuric acid. The reaction mixutre is then stirred for about 30 minutes, poured on to ice, filtered with suction, washed with water and dri... | CC1(C)C(=O)Nc2ccc([N+](=O)[O-])cc21 | null | null | null |
258,549 | ord_dataset-2369b9b9f44641b1930518c59ae89a95 | null | 1992-01-01T00:11:00 | true | [CH2:1]([C@@H:8]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:22])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([OH:25])[CH3:24].C1(C)C=CC=CC=1>>[CH2:23]([O:25][C:12]([C@H:13]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][C@@H:8]([CH2:1][C... | O=C1OC(=O)[C@H](Cc2ccccc2)C[C@H]1Cc1ccccc1 | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | The starting material is prepared as follows: 4.0 g of (S,S)-2,4-dibenzylglutaric anhydride is refluxed in 40 ml of ethanol:toluene (3:2) overnight. The reaction mixture is concentrated to yield 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyric acid as an oil. Oxalyl chloride (3.5 ml) is added to the solution of 4.5 g of 4-et... | CCOC(=O)[C@H](Cc1ccccc1)C[C@@H](Cc1ccccc1)C(=O)O | null | null | null |
316,440 | ord_dataset-fd1553bae35046c7a67523ff472cb5c3 | null | 1995-01-01T00:09:00 | true | [OH:1][C@H:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C@@H:4]([C:10]([CH3:12])=[CH2:11])[C@@H:3]1[C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[CH3:19]I>CN(C)C=O>[CH3:19][O:1][C@H:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C@@H:4]([C:10]([CH3:12])=[CH2:11])[C@@H:3]1[C:13]([O:15][CH3:16])=[O:14] | C=C(C)[C@@H]1CCC(C)(C)[C@H](O)[C@H]1C(=O)OC | CI | 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 | 3 | A mixture of the above alcohol (1.15 g) and sodium hydride (230 mg, 60% dispersion in oil) and methyl iodide (0.6 ml) in dry N,N-dimethylformamide was stirred for 3 hrs at room temperature. The mixture was cooled to 0° C., and reaction was quenched by addition of water. The pH of the mixture was adjusted to pH 7 with 0... | C=C(C)[C@@H]1CCC(C)(C)[C@H](OC)[C@H]1C(=O)OC | null | 92 | null |
1,381,047 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [NH2:1]/[C:2](/OCC)=[CH:3]\[C:4](=O)[C:5]([F:8])([F:7])[F:6].[CH3:13][NH:14][NH2:15]>CCO>[CH3:13][N:14]1[C:2]([NH2:1])=[CH:3][C:4]([C:5]([F:8])([F:7])[F:6])=[N:15]1 | CCO/C(N)=C/C(=O)C(F)(F)F | CNN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Using the procedure described in Example 161A Step 3, (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (2.34 g, 12.78 mmol) and methylhydrazine (0.645 g, 14 mmol) were reacted in EtOH (10 mL) at 95° C. for 8 hours, and purified by silica gel chromatography with 30-40% EtOAc/hexane as eluants to afford 1-methyl-3-(tri... | Cn1nc(C(F)(F)F)cc1N | null | 82.1 | null |
869,399 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [Li][CH2:2]CCC.[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])(=O)[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]=[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])[CH3:2] | CC(=O)c1cccc(C#N)c1 | [Li]CCCC | null | C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.5 | To the methyl triphenylphosphoniumbromide (4.3 grn, 12 mmol) in THF at 0° C., n-BuLi (1.6M, 7.5 ml, 12 mmol) was added and stirred for 30 min. Then 3-acetylbenzonitrile in THF was slowly added and the reaction mixture was stirred at 0° C. for further 3 h. Then reaction mixture was quenched with aqeous ammonium chloride... | C=C(C)c1cccc(C#N)c1 | null | 86 | null |
193,646 | ord_dataset-11b3c3b41eda49e196ec983a65d3b2c0 | null | 1989-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH3:14].C([Li])CCC.[O:20]1[C:22]([CH3:39])([CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:21]1.O>O1CCCC1>[CH3:12][O:11][C:6]1[C:7]([CH3:1... | CC(C)CCCC(C)CCCC(C)CCCC1(C)CO1 | COc1c(C)c(C)c(OC)c(C)c1C | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 1.8 g (9 mmol) of 2,5-dimethoxy-1,3,4,6-tetramethylbenzene were dissolved in 100 ml of tetrahydrofuran, treated with 1 g (9 mmol) of potassium tert.butylate and subsequently 6 ml (9.5 mmol) of n-butyllithium (1.6 molar) were added dropwise at room temperature. Thereafter, the mixture was stirred at room temperature for... | COc1c(C)c(C)c(OC)c(CCC(C)(O)CCCC(C)CCCC(C)CCCC(C)C)c1C | null | 88.6 | null |
1,337,580 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][N:11]3[C:16]4([CH2:21][CH2:20][N:19]([C:22]5[CH:31]=[N:30][C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]=5)[CH2:18][CH2:17]4)[CH2:15][CH2:14][CH2:13][C:12]3=[O:32])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:35]I.O>C1COCC1>[CH3:35][N:1]1[C:9]2[C:4](=[C:5]([CH2:10][N:11... | O=C1CCCC2(CCN(c3cnc4ccccc4n3)CC2)N1Cc1cccc2[nH]ccc12 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.17 | The title compound was synthesized from 1-((1H-indol-4-yl)methyl)-9-(quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one (prepared according to method G) via methylation as follows: NaH (7 mg, 0.18 mmol, 60% in mineral oil) was added to an ice-cold solution of 1-((1H-indol-4-yl)methyl)-9-(quinoxalin-2-yl)-1,9-diazaspiro[... | Cn1ccc2c(CN3C(=O)CCCC34CCN(c3cnc5ccccc5n3)CC4)cccc21 | null | 50 | null |
1,334,828 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[C:12]([C:28]4[NH:32][N:31]=NN=4)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:33][CH2:34][C:35](Cl)=[O:36]>C(Cl)(Cl)Cl>[Cl:33][CH2:34][C:35]1[O:36][C:28]([C:12]2[CH:1... | O=S(=O)(c1ccccc1)n1ncc2c(-c3nnn[nH]3)cc(-c3cccc4[nH]ccc34)cc21 | O=C(Cl)CCl | null | null | null | 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 | 100 | null | 6-(1H-Indol-4-yl)-1-(phenylsulfonyl)-4-(1H-tetrazol-5-yl)-1H-indazole (1.41 g, 3.19 mmol) was slurried into anhydrous chloroform (20 ml), treated with chloroacetyl chloride (1.023 ml, 12.78 mmol) and heated at 100° C. in a Biotage Initiator microwave for 30 mins, the mixture was split into 4 batches for the microwave r... | O=S(=O)(c1ccccc1)n1ncc2c(-c3nnc(CCl)o3)cc(-c3cccc4[nH]ccc34)cc21 | null | 15.2 | null |
744,839 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=1>C1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:1]([O:5][CH2:6][CH3:7])=[O:8])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:17]=1 | CCOC(=O)OCC | CCOC(=O)Cc1ccc(Br)cc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Under argon flow, 10.85 g of diethyl carbonate was dissolved in 60 ml of benzene, and 2.75 g of 60% sodium hydride was added and the mixture was heated to reflux. A solution of 5.58 g of ethyl 4-bromophenylacetate/20 ml of benzene was added dropwise to the solution over 1 hour, and the mixture was heated to reflux for ... | CCOC(=O)C(C(=O)OCC)c1ccc(Br)cc1 | null | 89.2 | null |
424,833 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N[C:14]1[CH:19]=CC(O)=C(CC=C)[CH:15]=1)(=O)C>>[CH2:19]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[CH:6]=[O:7])[CH:14]=[CH2:15] | O=Cc1ccc(O)cc1 | C=CCc1cc(NC(C)=O)ccc1O | null | null | null | null | null | null | null | 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 3-allyl 4-hydroxybenzaldehyde was prepared from 4-hydroxybenzaldehyde using the method described in Example 1 for the preparation of 4-acetamido-2-allylphenol. | C=CCc1cc(C=O)ccc1O | null | null | null |
606,770 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | Br.[Br:2][CH2:3][CH2:4][NH2:5].[CH2:6]([CH2:10][C:11](=O)[CH3:12])[C:7]([CH3:9])=O.C([O-])(=O)C.[K+]>C(O)(=O)C.O>[Br:2][CH2:3][CH2:4][N:5]1[C:11]([CH3:12])=[CH:10][CH:6]=[C:7]1[CH3:9] | CC(=O)CCC(C)=O | NCCBr | null | Br | CC(=O)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 80 | 2 | To a solution of 2-bromoethylamine hydrobromide (20.5 g, 0.1 mol) and acetonylacetone (12.5 ml, 0.1 mol) in acetic acid (10 ml) was added potassium acetate (10 g, 0.1 mol), and the mixture was stirred for 1 h at 20° C. and for 2 h at 80° C. The reaction mixture was diluted with water (150 ml) and extracted with diethyl... | Cc1ccc(C)n1CCBr | null | 46.8 | null |
212,905 | ord_dataset-e6e5ffd5405c481d8061087049155f9f | null | 1990-01-01T00:07:00 | true | C[O:2][C:3]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:13]([C:8]1[C:9]([OH:11])=[CH:10][C:3]([OH:2])=[C:4]([CH:7]=1)[CH:5]=[O:6])(=[O:15])[CH3:14] | COc1ccc(C=O)c(OC)c1 | CC(=O)Cl | null | Cl | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | null | To a mixture of 49.8 g of 2,4-dimethoxybenzaldehyde, 23.6 ml of acetyl chloride, and 1000 ml of methylene chloride cooled to approximately 0° C. were added 119.7 g of aluminum chloride with stirring under a nitrogen atmosphere. The reaction was allowed to warm to room temperature while stirring overnight. The mixture w... | CC(=O)c1cc(C=O)c(O)cc1O | null | null | null |
442,316 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]=[C:4]1[CH2:12][OH:13])[CH3:2].O[C:15]1[CH:47]=[CH:46][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[N:22]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]2... | O=C1SC(Cc2ccc(O)cc2)C(=O)N1C(c1ccccc1)(c1ccccc1)c1ccccc1 | CCn1c(CO)nc2cccnc21 | null | CCCCP(CCCC)CCCC | O=C(N=NC(=O)N1CCCCC1)N1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A procedure similar to that described in Preparation 4 was repeated, except that 0.5 g of 3-ethyl-2-hydroxymethylimidazo[5,4-b]pyridine (prepared as described in Preparation 28), 1.313 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 0.77 ml of tributylphosphine, 0.712 g of 1,1'-(azodicarbonyl)dipiperi... | CCn1c(COc2ccc(CC3SC(=O)N(C(c4ccccc4)(c4ccccc4)c4ccccc4)C3=O)cc2)nc2cccnc21 | null | null | null |
1,571,387 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][OH:18])[CH:8]3[N:9]=2)=[C:5]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:4]=[CH:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.CCCCCC>N1C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:18... | CN1C(=O)N(CCO)C2N=C3C(=C(c4ccco4)N=CN3N)N21 | 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 | CCCCCC | null | null | null | null | null | null | null | null | null | 26 | 16 | A mixture of 5-amino-8-(2-furyl)-3-(2-hydroxyethyl)-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one obtained in step 6 (3.5 g, 11 mmol), p-toluene sulphonylchloride (5.2 g, 27 mmol) were taken in pyridine (30 ml) and stirred at 25-27° C. for 16 hours. To the reaction mixture hexane (100 ml) was added and solid obtained was ... | Cc1ccc(S(=O)(=O)OCCN2C(=O)N(C)N3C4=C(c5ccco5)N=CN(N)C4=NC23)cc1 | null | 79.1 | null |
786,398 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([OH:24])=[O:23])[CH:14]([C:18]([F:21])([F:20])[F:19])[O:15]2)=[CH:10][C:9]=1[Cl:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([OH:24])=[O:23])[C@@H:14]([C:18]([F:20])([F:21])[F:19])[O:15]2)=[CH:10][C:9]... | O=C(O)C1=Cc2cc(Cl)c(Cc3ccccc3)cc2OC1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A racemic mixture of the compound prepared in Example 9k, Step 3 was chirally resolved using the same protocol as for Example 9d, Step 1 as peak 1 with retention time 4.27 min: ESHRMS m/z 367.0343 (M−H, C18H11ClF3O3, Calc'd 367.0329). 1HNMR (DMSO-d6/400 MHz) 13.34 (brs, 1H), 7.81 (s, 1H), 7.61 (s, 1H), 7.25-7.29 (m, 2H... | O=C(O)C1=Cc2cc(Cl)c(Cc3ccccc3)cc2O[C@@H]1C(F)(F)F | null | null | null |
1,176,068 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[C:4](=[O:23])[C:3]=1[C:24](=O)[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26].O.[NH2:35][NH2:36].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:27]1([CH:25]([C:24]2[C:3]3[C:4](=[O:23... | NN | CC(C(=O)c1c(O)c2cccnc2n(-c2cccc(OC(F)(F)F)c2)c1=O)c1ccccc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 115 | 2 | To a suspension of 4-hydroxy-3-(2-phenylpropionyl)-1-(3-trifluoromethoxyphenyl)-1,8-naphthyridin-2(1H)-one (276 mg, 0.61 mmol) produced in Synthesis Example 32 in DMF (3 mL) was added hydrazine monohydrate (purity of 80%, 100 μL), and the mixture was stirred at 110 to 120° C. for 2 hours. To the reaction solution was a... | CC(c1ccccc1)c1n[nH]c2c1c(=O)n(-c1cccc(OC(F)(F)F)c1)c1ncccc21 | null | null | null |
631,669 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]3[CH2:21][CH2:20][C:15]4(OCC[O:16]4)[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.Cl>O1CCCC1.CC(C)=O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]3[CH2:13][CH2:14][C:15](=[O:16])[CH2:20][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1 | Clc1ncnc2c1c(I)cn2C1CCC2(CC1)OCCO2 | null | null | Cl | 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 | 25 | 17 | A mixture of 4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (20 g, 47.7 mmol) and 6 N HCl(aq) (60 mL, 360 mmol) in tetrahydrofuran (120 mL) and acetone (600 mL) was stirred at ambient temperature under an atmosphere of nitrogen for 17 hours. The solvent was removed under reduced pressure an... | O=C1CCC(n2cc(I)c3c(Cl)ncnc32)CC1 | null | 68.6 | null |
534,632 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [C:1]([C:4]1[C:8]2[C:9](=[O:19])[CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][C:7]=2[O:6][CH:5]=1)(O)=[O:2].CC[N:22]=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.N>ClCCl.O>[C:1]([C:4]1[C:8]2[C:9](=[O:19])[CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][C:7]=2[O:6][CH:5]=1)(=[O:2])[NH2... | O=C(O)c1coc2c1C(=O)CC(c1ccccc1)C2 | CCN=C=NCCCN(C)C | null | N | On1nnc2ccccc21 | 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 | 12 | To a suspension of 3-carboxy-4-oxo-6-phenyl-4,5,6,7-tetrahydrobenzofuran (1.28 g) in dichloromethane (25 ml) were added, under ice-cooling, WSC (1.15 g) and N-hydroxybenzotriazole (0.92 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added concentrated ammonia solution (4.1 g), an... | NC(=O)c1coc2c1C(=O)CC(c1ccccc1)C2 | null | 28.2 | null |
1,198,311 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Cl:1][C:2]1[C:7](=[O:8])[N:6](C2CCCCO2)[N:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19].Cl>CO.O>[Cl:1][C:2]1[C:7](=[O:8])[NH:6][N:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19] | N#Cc1ccccc1Oc1cnn(C2CCCCO2)c(=O)c1Cl | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 90 | 4 | A solution of 2-[5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yloxy]-benzonitrile (61.8 g, 0.19 mol) in methanol (370 mL) was treated with a 6N aqueous hydrochloric acid solution (185 mL). The reaction was stirred at 90° C. for 4 h and then was allowed to cool to 25° C. The reaction was diluted with... | N#Cc1ccccc1Oc1cn[nH]c(=O)c1Cl | null | 91.6 | null |
1,287,524 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:50])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][C@@H:32]([C:34]([O:36]CC3C=CC=CC=3)=[O:35])[CH3:33])[N:28]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH... | CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)c2cc(O[C@H](C)C(=O)OCc3ccccc3)n(-c3ccccc3)n2)CC1 | null | null | null | 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 | 16 | To a solution of 5.90 g 4-((S)-2-{[5-((R)-1-Benzyloxycarbonyl-ethoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 30 ml ethyl acetate were added under argon 1.0 g Pd/C (10%) and the suspension was stirred under an atmosphere of hydrogen (1 bar) for ... | CCOC(=O)N1CCN(C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)c2cc(O[C@H](C)C(=O)O)n(-c3ccccc3)n2)CC1 | null | null | null |
1,469,553 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | C(OC([N:8]1[C:11]2([CH2:14][N:13]([C:15](=[O:26])[NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36]>>[C:20]1([CH2:19][CH2:18][CH2:17][NH:16][C:15]([N:13]2[... | CC(C)(C)OC(=O)N1CCC12CN(C(=O)NCCCc1ccccc1)C2 | O=S(=O)(Cl)c1ccccc1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the experimental procedure of example 6b) 6-(3-phenyl-propylcarbamoyl)-1,6-diaza-spiro[3.3]heptane-1-carboxylic acid tert-butyl ester instead of tert-butyl 1-(2,4-dichlorobenzylcarbamoyl)-1,6-diazaspiro[3.3]heptane-6-carboxylate was converted using 2-trifluoromethylbenzene-1-sulfonyl chloride instead of 4... | O=C(NCCCc1ccccc1)N1CC2(CCN2S(=O)(=O)c2ccccc2C(F)(F)F)C1 | null | null | null |
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