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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
5,800 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [CH:1](=O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1>>[CH3:14][C:12]1([CH3:15])[N:13]=[C:9](/[CH:8]=[CH:1]/[C:2]2[O:6][CH:5]=[CH:4][CH:3]=2)[O:10][CH2:11]1 | CC1=NC(C)(C)CO1 | O=Cc1ccco1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4,4-Dimethyl-2(2-α-furylethenyl)-2-oxazoline (P-1906) was prepared by reacting furfural with 2,4,4-trimethyl-2-oxazoline. The product had a boiling point of 87° at 0.14 mm and the nmr spectrum and infra-red absorption spectrum were consistent with the proposed structure. The oral LD0 by adminstration to mice was 50 mg/... | CC1(C)COC(/C=C/c2ccco2)=N1 | null | null | null |
1,476,056 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-])=O.[H][H]>C(O)C.[Pd]>[N:11]1([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[NH2:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | O=[N+]([O-])c1cc[n+]([O-])cc1N1CCCCC1 | [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 | 15 | To a solution of 4-nitro-3-(piperidin-1-yl)pyridine 1-oxide (1.0 equiv.) in ethanol, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 15 hours. At this time LC/MS analysis indicated that the nitro w... | Nc1ccncc1N1CCCCC1 | null | 73 | null |
924,091 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | C(O)C.[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:31])[CH:11]=[C:12]([C:29]#[N:30])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-])=O)=[CH:16][CH:15]=1)=[O:8])[CH3:5].[H][H]>[Pd].C(OCC)(=O)C>[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:31])[CH:11]=[C:12]([C:29]#[N:30])[C:13]=1[C:14]1[CH:... | [H][H] | CCOC(=O)c1c(-c2ccc(-c3ccccc3[N+](=O)[O-])cc2)c(C#N)cn1C | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCO | null | null | null | null | null | null | null | null | null | null | 18 | Add a 1:1 ethanol:ethyl acetate mixture to palladium on carbon (catalytic, 0.30 g) followed by 3(2′-nitro-biphenyl-4-yl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (3.00 g, 8.30 mmol, prepared in example E-9) with stirring. Subject the reaction to an atmosphere of hydrogen gas. After 18 hours, filter and... | CCOC(=O)c1c(-c2ccc(-c3ccccc3N)cc2)c(C#N)cn1C | null | null | null |
136,052 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [NH2:1][CH2:2][CH2:3][N:4]1[N:8]=[N:7][C:6]([CH2:9][O:10][CH2:11][C:12]2[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[Cl:30])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:5]1.[CH3:36][S:37][C:38](SC)=[N:39][C:40]#[N:41]>CC(O)C>[Cl:30][C:24... | CSC(=NC#N)SC | CCOC(=O)C1=C(COCc2nnn(CCN)n2)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-(2-aminoethyl)-5-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}tetrazole (1.04 g) and dimethyl N-cyanoimidodithiocarbonate (0.30 g) in propan-2-ol (10 ml) was heated under reflux for 16 hours and then evaporated. The residual oil was triturate... | CCOC(=O)C1=C(COCc2nnn(CCNC(=NC#N)SC)n2)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | 60.8 | null |
1,460,307 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[O:2]=[C:3]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:14]([C@H:21]1[CH2:25][NH:24][C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14](... | O=C(O)CCC(=O)c1cccs1 | O=C(Nc1ccc(Oc2ccc(F)cc2)cc1)[C@@H]1C[C@@H](Cc2ccccc2)CN1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Proceeding as in Example 1, but substituting 4-oxo-4-(thien-2-yl)butanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 91, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxo-4-(thien-2-yl)butanoyl)pyrrolidine-2-carboxamide (10.8 mg, 32.3%). Major iso... | O=C(CCC(=O)N1C[C@H](Cc2ccccc2)C[C@H]1C(=O)Nc1ccc(Oc2ccc(F)cc2)cc1)c1cccs1 | null | 32.3 | null |
543,132 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | [NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[N:2]1.C(=O)([O-])[O-].[Na+].[Na+].I[CH:16]([CH3:18])[CH3:17]>CN(C)C=O>[CH:16]([N:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[N:2]1)([CH3:18])[CH3:17] | CC(C)I | OCCc1cc[nH]n1 | 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 | null | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 1.0 gm (9.0 mMol) 2-(3-pyrazolyl)-1-ethanol in 36 mL dimethylformamide were added 2.38 gm (22.5 mMol) sodium carbonate followed by the dropwise addition of a solution of 0.89 mL (9.0 mMol) 2-iodopropane in 8 mL dimethylformamide. The reaction mixture was heated to 100° C. for 18 hours. The reaction mix... | CC(C)n1ccc(CCO)n1 | null | 25.9 | null |
1,072,463 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]=[C:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[N:6][CH:7]=1.O(C1C=CC=CC=1)C1C=CC=CC=1>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:16](=[O:18])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8]2)=[N:6][CH:7]=1 | CCOC(=O)C(=CNc1cncc(Br)c1)C(=O)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | CC#N | null | null | null | null | null | null | null | null | null | 25 | null | In a RBF fitted with a reflux condenser a mixture of diethyl 2-((5-bromopyridin-3-ylamino)methylene)malonate (1 g, 3 mmol) and 1-phenoxybenzene (10 mL, 63 mmol) was heated to reflux for 1 h. The reaction mixture was allowed to cool to RT and CH3CN was added. The resulting solids were filtered and dried to provide the d... | CCOC(=O)c1c[nH]c2cc(Br)cnc2c1=O | null | null | null |
771,839 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:14]([CH3:27])=[C:13]([CH3:28])[N:12]=1.O>O1CCCC1>[CH3:28][C:13]1[C:14]([CH3:27])=[C:15]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:16]([N+:... | Oc1ccccc1 | Cc1nc(Cl)c([N+](=O)[O-])c(NCCCCCO)c1C | 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 | 25 | null | Under a nitrogen atmosphere, tetrahydrofuran (THF) (150 mL) was cooled to 0° C. Sodium hydride (9.30 g, 233 mmol), available as a 60% dispersion in mineral oil, was added with stirring. A solution of phenol (21.1 g, 225 mmol) in THF (80 mL) was added dropwise over a period of one hour. A solution of 5-(2-chloro-5,6-dim... | Cc1nc(Oc2ccccc2)c([N+](=O)[O-])c(NCCCCCO)c1C | null | 75.2 | null |
1,698,145 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH:1]1([N:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:5]2[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.[NH2:29][C:30]1[CH:31]=[C:32]([N:47]([CH2:52][C:53]2[CH:58]=[CH:57][C:56]([O:59][CH3:60])=[CH:55][CH:54]=2)[C:48](=[O:51])[O:49][CH3:5... | COc1ccc(CN(c2nc(S(C)(=O)=O)nn3c(C#N)cnc23)C2CC2)cc1 | COC(=O)N(Cc1ccc(OC)cc1)c1cc(N)c(F)c(N2CCN(C3COC3)CC2)c1 | null | O=C([O-])[O-] | [Cs+] | 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 | 45 | 16 | 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate 3) (58.4 mg, 0.146 mmol), methyl (3-amino-4-fluoro-5-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)(4-methoxybenzyl)carbamate (62 mg, 0.098 mmol) and Cs2CO3 (95 mg, 0.293 mmol) in DMF (1 ml) were heated at 70° C. ... | COC(=O)N(Cc1ccc(OC)cc1)c1cc(Nc2nc(N(Cc3ccc(OC)cc3)C3CC3)c3ncc(C#N)n3n2)c(F)c(N2CCN(C3COC3)CC2)c1 | null | 179.8 | null |
187,152 | ord_dataset-3ec273742a0345ea916ad5fd071167f2 | null | 1989-01-01T00:04:00 | true | [NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][C:21]([O:23]C)=O)[CH:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CO>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])... | CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OCC(=O)OC | C1CCNC1 | 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 solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-methoxy-2-oxoethoxy)benzamide (1.07 g, 3 mmoles) (prepared in Example 15) in methanol (10 ml) and pyrrolidine (0.952 g, 23 mmoles) was refluxed overnight. The solvent was evaporated and the residue was chromatographed over deactivated silica using methylene ... | CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OCC(=O)N1CCCC1 | null | 72.2 | null |
667,087 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][NH2:11]>C1COCC1>[CH3:10][NH:11][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1 | N#Cc1ccnc(Cl)n1 | CN | 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 | 8 | 2-Chloro-4-pyrimidinecarbonitrile (14.1 g, 101 mmol, prepared according to the procedure of Daves et. al J. Het. Chem. 1964, 1, 130-132) in 100 ml THF was cooled to 0° C. Reaction progress was monitored as aliquots of methylamine solution (in THF, 2.0 M, Aldrich) were added dropwise over the course of 1 h (58 ml+15 ml+... | CNc1nccc(C#N)n1 | null | null | null |
307,009 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | I.C[O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11]C)[CH:5]=1>>[CH3:10][C:8]1[CH:7]=[C:6]([OH:11])[CH:5]=[C:4]([CH:9]=1)[OH:3] | COc1cc(C)cc(OC)c1 | null | null | I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3 | Methylmagnesium bromide (35 g) was added to 1,3-dimethoxy-5-benzoyl chloride (100 g) to obtain 1,3-dimethoxy-methylphenone in a yield of 45%. Then, the reduction was conducted by adding water (300 cc), concentrated hydrochloric acid (300 cc) and 1,3-dimethoxy-methylphenone (100 g) to zinc amalgam obtained from zinc (40... | Cc1cc(O)cc(O)c1 | null | null | null |
607,877 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)[CH:5]=O.N1(C2C=C[C:23]([CH:24]=[O:25])=CC=2)C=CC=N1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:23][CH:24]=[O:25])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][CH:12]=[N:11]1 | O=Cc1ccc(-n2cccn2)cc1 | O=Cc1ccc(-n2cncn2)c(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 | The title compound was prepared by a procedure analogous to Reference Example 30 by substituting 3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzaldehyde (prepared as described in Reference Example 7) for the 4-(1H-pyrazol-1-yl)-benzaldehyde of Reference Example 30. MS 218 (M+H)+. | O=CC=Cc1ccc(-n2cncn2)c(F)c1 | null | null | null |
1,007,287 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[CH3:10][C:11]1([CH3:29])[O:15][N:14]=[C:13]([S:16][CH2:17][C:18]2[C:19]([OH:28])=[N:20][N:21]([CH3:27])[C:22]=2[C:23]([F:26])([F:25])[F:24])[CH2:12]1.O>CN(C)C=O>[CH3:10][C:11]1([CH3:29])[O:15][N:14]=[C:13]([S:16][CH2:17][C:18]2[C:19]([O:28][CH2:7][CH3:8])=[N:20][N:21]([CH3:2... | CCI | Cn1nc(O)c(CSC2=NOC(C)(C)C2)c1C(F)(F)F | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 50 | 3 | 0.20 g (1.3 mmoles) of anhydrous potassium carbonate and 0.20 g (1.5 mmoles) of ethyl iodide were added to a solution of 0.30 g (1.0 mmoles) of 5,5-dimethyl-3-(3-hydroxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at 50° C. for... | CCOc1nn(C)c(C(F)(F)F)c1CSC1=NOC(C)(C)C1 | null | 88.9 | null |
1,081,617 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([C:16]([F:19])([F:18])[F:17])=[N:14][N:15]=3)[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[S:20]1[CH:24]=[C:23]([CH:25]=O)[N:22]=[N:21]1>>[S:20]1[CH:24]=[C:23]([CH2:25][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]4[N:11]([C:13]([C:16]([F:17])([F:18])[F:19])=[N:14][N:... | FC(F)(F)c1nnc2ccc(N3CCNCC3)nn12 | O=Cc1csnn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Reductive amination of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine with thiadiazole-4-carbaldehyde was carried out according to General Synthetic Method 5. The crude product was purified by hplc using a Waters XBridge Prep C18 OBD column (5μ silica, 19 mm diameter, 100 mm length) eluted with... | FC(F)(F)c1nnc2ccc(N3CCN(Cc4csnn4)CC3)nn12 | null | null | null |
104,828 | ord_dataset-b2a00a09c8494aaf9348c3a3af29d26e | null | 1983-01-01T00:04:00 | true | [CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:15][CH3:16])[C:12](O)=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(Cl)([Cl:19])=O>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:15][CH3:16])[C:12]([Cl:19])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3] | O=S(Cl)Cl | CCC(C(=O)O)c1ccc(CC(C)C)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 110 g of 2-(4-isobutylphenyl)butyric acid and 89 g of thionyl chloride are heated on a water bath until the gas evolution ceases. An excess of thionyl chloride is removed by distillation, A residue of 117 g of 2-(4-isobutylphenyl)butyric chloride is obtained. | CCC(C(=O)Cl)c1ccc(CC(C)C)cc1 | null | 98.1 | null |
1,092,400 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.Br[C:42]1[CH:47]=[CH:46... | CCN1CCN(C(=O)c2ccc(Br)c(C)c2)CC1 | COc1ccc(CN(Cc2ccc(OC)cc2)c2ncc(-c3nc(N4CCOCC4)nc4c3CCN4)cn2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (100 mg) and (4-bromo-3-methyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (162 mg) instead of 4-chloropicolinic acid t-butylamide, in the same manner as Example 1-D-07, a crude product of [4-(4-{2-[bis-(... | CCN1CCN(C(=O)c2ccc(N3CCc4c(-c5cnc(N(Cc6ccc(OC)cc6)Cc6ccc(OC)cc6)nc5)nc(N5CCOCC5)nc43)c(C)c2)CC1 | null | null | null |
924,433 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:22](OC(C)(C)C)(=[O:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH2:10][C:22](=[O:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C... | CC(C)(C)OC(=O)C(=O)OC(C)(C)C | CC(=O)c1cc(Cl)cc(Cl)c1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of the product from step B (4.1 g, 21.7 mmol) in 100 mL of diethyl ether at −78° C. was added lithium bis(trimethylsilyl)amide (23.9 mL, 23.9 mmol). After 50 min at −78° C. di-tert-butyl oxalate (4.18 g, 20.66 mmol) was added as a solid. The cold bath was removed and after 2 h an additional portion of di-... | CC(C)(C)OC(=O)C(=O)CC(=O)c1cc(Cl)cc(Cl)c1 | null | null | null |
431,214 | ord_dataset-64e3763e75b242749501bacdc0c8baef | null | 1999-01-01T00:05:00 | true | [N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=2)[NH2:10])[CH:4]=[N:3][CH:2]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[C:7]([C:5]2[CH:6]=[N:1][CH:2]=[N:3][CH:4]=2)[CH:8]=1)(=[O:16])[CH3:15] | Nc1cccc(-c2cncnc2)c1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2b is acetylated with acetic anhydride to afford 2c (15.4g, 82%). Mp 157-158° C. | CC(=O)Nc1cccc(-c2cncnc2)c1 | null | 82 | null |
919,850 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[Cl:13][C:14]1[S:15][C:16]([S:20](Cl)(=[O:22])=[O:21])=[CH:17][C:18]=1[Cl:19]>>[Cl:19][C:18]1[CH:17]=[C:16]([S:20]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=2)(=[O:22])=[O:21])[S:15][C:14]=1[Cl:13] | CCOC(=O)Cc1csc(N)n1 | O=S(=O)(Cl)c1cc(Cl)c(Cl)s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from ethyl 2-amino-4-thiazolylacetate and 2,3-dichlorothiophene-5-sulfonyl chloride as described in the synthetic METHOD B to give a white-yellow solid (36.9 mg) with purity >90%. MS (pos) m/z 401.1, 403.1. | CCOC(=O)Cc1csc(NS(=O)(=O)c2cc(Cl)c(Cl)s2)n1 | null | null | null |
1,361,323 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:21]=[CH:20][C:10]([CH:11]=[C:12]2[S:16][C:15](SC)=[N:14][C:13]2=[O:19])=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[NH:26]1[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]1>CN(C=O)C>[CH:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:21]=[CH:20][C:10]([C... | CSC1=NC(=O)C(=Cc2ccc(Oc3ccccc3C(C)C)cc2)S1 | O=C(O)C1CNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | was prepared from 5-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-methylsulfanyl-thiazol-4-one and azetidine-3-carboxylic acid and substituting MeCN with DMF as described in Example 5C | CC(C)c1ccccc1Oc1ccc(C=C2SC(N3CC(C(=O)O)C3)=NC2=O)cc1 | null | null | null |
151,340 | ord_dataset-772de90433b44abbbacf9b316b845c31 | null | 1986-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:11][CH2:10]1.C(N(CC)CC)C.[C:35](Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4... | CC(C)(C)C(=O)Cl | COc1ccccc1N1CCN(CCc2ccc(O)c3ncccc23)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 48 | A mixture of 7.27 g of 5-{2-[4-(2-methoxyphenyl)piperazinyl]ethyl}-8-hydroxy quinoline in 150 ml of anhydrous tetrahydrofuran in the presence of 3.1 ml of triethylamine and 5 ml of pivaloyl chloride is stirred for 48 hours at room temperature. After evaporation of the tetrahydrofuran, the residue is taken up in chlorof... | COc1ccccc1N1CCN(CCc2ccc(OC(=O)C(C)(C)C)c3ncccc23)CC1 | null | null | null |
1,328,385 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl.CO[CH:4]([O:21]C)[CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)=[O:8]>CC(C)=O>[OH:21][CH:4]1[N:10]2[C:11]3[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][C:16]=3[CH:17]=[C:9]2[C:7](=[O:8])[NH:6][CH2:5]1 | COC(CNC(=O)c1cc2cc([N+](=O)[O-])ccc2[nH]1)OC | null | null | Cl | 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 | null | null | HCl 2N (13.75 ml, 27.5 mmol, 2.5 eq.) was added to a solution of the compound of formula (IV) (3 g, 11 mmol, 1 eq.) in acetone (200 ml), the final solution was stirred at 25° C. for 48 h. The solution was dried under reduced pressure affording the compound of formula (V) as yellow solid that was used in the subsequent ... | O=C1NCC(O)n2c1cc1cc([N+](=O)[O-])ccc12 | null | 97 | null |
425,412 | ord_dataset-1ecf96d88f254270bff816ee7eeffef6 | null | 1999-01-01T00:02:00 | true | [NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)[CH3:18])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].C(O)(=O)C.[N:32](OCCC(C)C)=O>C(Cl)(Cl)Cl>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:17]([CH2:16][... | COC(=O)C(N)Cc1ccc(OCCN(C)c2nc3ccccc3o2)cc1 | CC(C)CCON=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of methyl 2-amino-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]propanoate (5.00 g), acetic acid (4.4 mL) and chloroform (160 mL) was treated dropwise with isoamyl nitrite (3.2 mL). The mixture was heated at reflux for 1.5 hrs, cooled, diluted with chloroform (200 mL) and washed successively with di... | COC(=O)C(Cc1ccc(OCCN(C)c2nc3ccccc3o2)cc1)=[N+]=[N-] | null | null | null |
581,821 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8](COC)[C:7]=2[CH:19]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[NH:8][C:7]=2[CH:19]=1 | COCN1c2cc(CCl)ccc2Sc2nccnc21 | null | null | O=C([O-])O | [Na+] | 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 | 0 | 12 | Into 250 ml of a solution of 26.9 g of 8-chloromethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in methylene chloride was dropped 50 ml of trifluoroacetic acid at 0° C. After reacting at room temperature for 12 hours, the reaction mixture was cooled to 0° C. and neutralized by adding an aqueous solution of... | ClCc1ccc2c(c1)Nc1nccnc1S2 | null | 83.5 | null |
1,495,084 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [CH3:1][O:2][C:3]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:4].O=[C:26]1[CH2:31][N:30]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:29]([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[C@@H:28]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53... | CC(C)(C)OC(=O)[C@H]1CC(=O)CN(C(=O)OCc2ccccc2)[C@@H]1C(=O)OCc1ccccc1 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | 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 | 8 | To an oven-dried 25 mL round-bottomed flask equipped with a magnetic stir bar and under a nitrogen gas atmosphere was placed methyl (triphenylphosphoranylidene) acetate (199 mg, 0.597 mmol) and toluene (5 mL). To this heterogeneous solution was added a solution of 1,2-dibenzyl 3-tert-butyl (2S,3S)-5-oxopiperidine-1,2,3... | COC(=O)C=C1C[C@H](C(=O)OC(C)(C)C)[C@@H](C(=O)OCc2ccccc2)N(C(=O)OCc2ccccc2)C1 | null | 79.7 | null |
1,078,807 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[CH:19][C:18]([C:21]4[C:22]([CH3:32])=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=4)[C:26](O)=[O:27])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[C:39]1([NH2:42])[CH2:41][CH2:40]1.C1C=CC2N(O)N... | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)O)c(OC)cc3C)cc12 | NC1(c2ncccn2)CC1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 12 | To a mixture of 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-2-methoxy-4-methylbenzoic acid (0.2 g, 0.46 mmol, 1 eq), 1-(pyrimidin-2-yl)cyclopropanamine (0.074 g, 0.55 mmol, 1.2 eq), HOBT (0.105 g, 0.77 mmol, 1.7 eq), EDC.HCl (0.0.158 g, 0.82 mmol, 1.8 eq), in DCM at ambient temperature and under nitrogen ... | CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cc(C(=O)NC4(c5ncccn5)CC4)c(OC)cc3C)cc12 | null | null | null |
609,809 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [CH3:1][C:2]1[C:7](C)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10]C1C=CC(C)=CC=1O>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:10])[CH:5]=[CH:4][C:3]=1[OH:9] | Cc1ccc(C)c(O)c1 | Cc1cccc(O)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 | 2,3-dimethylphenol; 2,5-dimethylphenol; | Cc1ccc(O)c(C)c1 | null | null | null |
911,363 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [OH-].[Na+].[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].Cl>CO.O1CCOCC1>[C:3]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4] | COC(=O)c1ccc(C(C)=O)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 25 | 12 | A solution of NaOH (1.7 g/12 ml) was added to methyl 4-acetylbenzoate (5.04 g, 28.3 mmol) in MeOH-dioxane (2:1, 60 ml). After stirring at room temperature for 12 hr, the mixture was acidified with 5N HCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4. Evaporation of solven... | CC(=O)c1ccc(C(=O)O)cc1 | null | null | null |
1,372,003 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.CC1C=CC(S(O[CH2:29][CH2:30][CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:8][C:6]1[CH:7]=[C:2]([O:1][CH2:29][CH2:30][CH2:31][S:32]([CH3:35])(=[O:3... | Cc1ccc(S(=O)(=O)OCCCS(C)(=O)=O)cc1 | Cc1cc(O)cc(C)c1-c1cccc(C=O)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 90 | 24 | To a solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.26 g, 10.0 mmol) and 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (3.51 g, 12.0 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (1.80 g, 13.0 mmol), and the mixture was stirred at 90° C. for 24 hr under nitrogen atmosphere. W... | Cc1cc(OCCCS(C)(=O)=O)cc(C)c1-c1cccc(C=O)c1 | null | 77.4 | null |
1,104,291 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:18].CS[C:21](=[N:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[NH:22][C:23]#[N:24].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[O:18]=[C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14]... | NCCCCCCn1c(=O)ccc2ccccc21 | CSC(=Nc1ccncc1)NC#N | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | c1ccncc1 | null | null | null | null | null | null | null | null | null | 60 | 8 | A mixture of 1-(6-amino-1-hexyl)-1,2-dihydroquinoline-2-one (320 mg), S-methyl-N-cyano-N′-4-pyridyl-isothiourea (210 mg), triethylamine (0.31 ml), 4-(N,N-dimethylamino)-pyridine (7 mg) and pyridine (10 ml) was stirred overnight at 60° C. After cooling to room temperature the pyridine was removed by evaporation twice wi... | N#CNC(=Nc1ccncc1)NCCCCCCn1c(=O)ccc2ccccc21 | null | null | null |
1,445,263 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | CC1(C)CO[C:5]2([CH2:32][CH2:31][C:8]3([O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]4[CH:22]=[CH:21][C:20]([C:23]5[CH:28]=[CH:27][N:26]([CH3:29])[C:25](=[O:30])[CH:24]=5)=[CH:19][CH:18]=4)[CH3:16])[CH2:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]C1>O>[CH3:29][N:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C@@H:15]([N:11]3... | C[C@@H](c1ccc(-c2ccn(C)c(=O)c2)cc1)N1CCC2(CCC3(CC2)OCC(C)(C)CO3)OC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 12,12-dimethyl-3-{(S)-1-[4-(1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-phenyl]-ethyl}-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one following a procedure analogous to that described in Step 10 of Intermediate 2. Yield: 48% of theory; Mass spectrum (ESI+): m/z=395 [M+H]+; 1H NMR ... | C[C@@H](c1ccc(-c2ccn(C)c(=O)c2)cc1)N1CCC2(CCC(=O)CC2)OC1=O | null | 48 | null |
1,686,067 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:27][S:28]([O:11][CH2:10][C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[C:4]... | CS(=O)(=O)Cl | CC(C)(C)OC(=O)N[C@H](CO)c1cc(F)cc(Br)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 0 | 1 | To a stirred solution of (S)-tert-butyl (1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamate (4.8 g, 14.36 mmol) in anhydrous DCM (100 mL) at 0° C. was added triethylamine (4.00 mL, 28.7 mmol) followed by methanesulfonyl chloride (1.343 mL, 17.24 mmol). The reaction was stirred at 0° C. for 1 hr, by which time the LCMS... | CC(C)(C)OC(=O)N[C@H](COS(C)(=O)=O)c1cc(F)cc(Br)c1 | null | 100 | null |
591,191 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[NH:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[CH:37]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C... | O=Cc1ccc[nH]1 | O=C(Nc1ccc(N2CCNCC2)cc1)c1ccccc1-c1ccc(C(F)(F)F)cc1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCCl | null | null | null | null | null | null | null | null | null | 0 | 16 | To a solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide (310 mg) in 1,2-dichloroethane (20 mL) was added 1H-pyrrole-2-carboxaldehyde (95 mg) and acetic acid (67 mg). The solution was cooled at 0° C. and sodium triacetoxy borohydride (317 mg) was added portionwise and the mixture w... | O=C(Nc1ccc(N2CCN(Cc3ccc[nH]3)CC2)cc1)c1ccccc1-c1ccc(C(F)(F)F)cc1 | null | 49 | null |
535,944 | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | null | 2002-01-01T00:03:00 | true | [Cl-].[CH:2]1([CH2:8][NH2+:9][CH2:10][CH2:11]Cl)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]=[C:24]=[S:25]>>[CH3:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]=[C:24]1[N:9]([CH2:8][CH:2]2[CH2:7][CH2:6][CH2:5][CH2... | ClCC[NH2+]CC1CCCCC1 | Cc1cc([N+](=O)[O-])ccc1N=C=S | null | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-Hydroxyethylamine was reacted with cyclohexylmethyl bromide according to Method B2a to give N-cyclohexylmethyl-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to give N-cyclohexylmethyl-N-(2-chloroethyl)ammonium chloride. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl... | Cc1cc([N+](=O)[O-])ccc1N=C1SCCN1CC1CCCCC1 | null | null | null |
404,919 | ord_dataset-55e306db9b6b4befbc22504c12b7113d | null | 1998-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:18])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]#[N:17])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+].CCOCC>C1COCC1>[NH2:17][CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:18])[CH2:13][CH2:12]1 | N#CCCN1CCC(O)(c2ccc(Cl)cc2)CC1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred solution of 3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]propionitrile (3.51 g, 13.2 mmol, 1.0 equiv) in anhydrous THF (20 mL) under argon was added a solution of BH3 in THF (1.0M, 46.4 mL, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours and then cooled to room temperature. Aqueous ... | NCCCN1CCC(O)(c2ccc(Cl)cc2)CC1 | null | 87.4 | null |
677,452 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | [C:1]([C:6]1[CH:34]=[CH:33][C:9]2[N:10]([CH2:14][CH2:15][O:16][C:17]3[CH:32]=[CH:31][C:20]([CH2:21][CH:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=3)[C:11](=[O:13])[S:12][C:8]=2[CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4]>CCCCCC>[CH2:1]([C:6]1[CH:34]=[CH:33][C:9]2[N:10]([CH2:14][CH2:15][O:16][... | CCCC(=O)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)C(=O)OC)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | The procedure is as in Example 48, starting from the compound obtained in Example 53. The recrystallisation solvent is hexane. | CCCCc1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)C(=O)OC)cc1 | null | null | null |
580,727 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | [NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[P:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:4... | O=C(Cl)c1ccccc1 | Nc1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12 | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 5 | 1.00 gram (2.21 mmol) of (−)-2-amino-2′-diphenylphosphino-1,1′-binaphthyl (the formula (1-1a)) was dissolved in 44 ml of methylene chloride, followed by the addition of 0.21 ml (2.65 mmol) of pyridine and 0.28 ml (2.43 mmol) of benzoyl chloride under 0° C. The reaction mixture was stirred at room temperature for 5 hour... | O=C(Nc1ccc2ccccc2c1-c1c(P(c2ccccc2)c2ccccc2)ccc2ccccc12)c1ccccc1 | null | 94.1 | null |
1,557,762 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[CH:23][N:24]([CH2:26][CH2:27][C:28](=[O:30])[CH3:29])[CH:25]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:31][Mg]Br.[NH4+].[Cl-]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([C... | CC(=O)CCn1cnc(C(=O)N[C@@H](C)Cn2ccc(-c3ccc(C#N)c(Cl)c3)n2)c1 | C[Mg]Br | null | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | 45 | 3 | (S)—N-{1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1-(3-oxobutyl)-1H-imidazole-4-carboxamide (100 mg, 1.18 mmol) in dry THF (3 ml) was added to 3.0 M methylmagnesium bromide solution in ether (0.39 ml) at 30-40° C. Thereafter the reaction mixture was stirred at 45° C. for 3 h. The cooled reaction mixture... | C[C@@H](Cn1ccc(-c2ccc(C#N)c(Cl)c2)n1)NC(=O)c1cn(CCC(C)(C)O)cn1 | null | null | null |
1,654,800 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | C([O:8][C:9]1[C:10]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[F:27])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:27][C:20]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]=1[C:10]1[C:9]([OH:8])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:... | COC(=O)c1cnc(-c2cc(OC)ccc2F)c(OCc2ccccc2)c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 20 | Under a nitrogen atmosphere, to a solution of methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate (1.50 g) in ethyl acetate (20 mL) was added 10% palladium-activated carbon (433 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature for 20 hr. The reaction mixture was filtered through c... | COC(=O)c1cnc(-c2cc(OC)ccc2F)c(O)c1 | null | 88.3 | null |
1,152,211 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | Br.Br.[CH3:3][C@@H:4]1[CH2:9][NH:8][C@H:7]([CH3:10])[CH2:6][NH:5]1.[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](Cl)=[N:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>C(OCC)(=O)C>[Cl:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([N:5]2[CH2:6][C@@H:7]([CH3:10])[NH:8][CH2:9][C@H:... | C[C@@H]1CN[C@H](C)CN1 | Clc1nnc(Cl)c2ccccc12 | null | Br | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | (2R,5R)-2,5-dimethylpiperazine dihydrobromide (2.08 g, 7.54 mmol), 1,4-dichlorophthalazine (0.500 g, 2.52 mmol), potassium carbonate (2.08 g, 15.0 mmol), and N-methylpyrrolidinone (7 mL) were heated at 120° C. for 6 hours. The reaction was taken up in ethyl acetate (75 mL) washed with aqueous K2CO3 (10%), water, and th... | C[C@@H]1CN(c2nnc(Cl)c3ccccc23)[C@H](C)CN1 | null | null | null |
955,661 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Br:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1.[CH:13]([NH2:16])([CH3:15])[CH3:14]>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([NH:16][CH:13]([CH3:15])[CH3:14])[C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1 | O=c1[nH]nc2c(Cl)nc(Br)cn12 | CC(C)N | 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 | null | A solution of 0.50 g of the product of Step D and 0.59 g of isopropylamine in THF (20 mL) was heated to reflux. After one h, the reaction was concentrated and the residue partitioned between EtOAc and water. The layers were separated and the organic phase was washed with sat sodium chloride solution, dried over magnesi... | CC(C)Nc1nc(Br)cn2c(=O)[nH]nc12 | null | null | null |
351,686 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1)=O.[CH:10]1([CH2:13][NH2:14])[CH2:12][CH2:11]1>>[CH:10]1([CH2:13][N:14]=[CH:1][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=2)[CH2:12][CH2:11]1 | NCC1CC1 | Cc1cc(C=O)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 | Reaction of 4-formyl-2-methylpyridine [prepared in Example 33(a)] and cyclopropylmethyl amine by the procedure of example 1(c) affords the title compound as a yellow oil. | Cc1cc(C=NCC2CC2)ccn1 | null | null | null |
1,454,479 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][N:19]=2)=[CH:4][CH:3]=1.[CH2:26]([O:28][C:29]([C:31]1([C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)[CH2:33][CH2:32]1)=[O:30])[CH3:27]>>[CH2:26]([O... | CCOC(=O)C1(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1 | Cc1noc(-c2ccc(Br)cc2)c1Cc1nnc(-c2ccccc2)o1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 4, using 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-5-phenyl-[1,3,4]oxadiazole and 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester. | CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4Cc4nnc(-c5ccccc5)o4)cc3)cc2)CC1 | null | null | null |
415,023 | ord_dataset-1cb9d78632144c5f8acfc3e9ff388678 | null | 1998-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](Cl)=[N:10][C:4]=2[CH:3]=1.[CH2:18]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].N12CCCN=C1CCCCC2>C(#N)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][C... | ClC1=Nc2cc(Cl)ccc2Oc2ccccc21 | CCCCCCCCCN1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | null | The mixture of 8,11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) wer... | CCCCCCCCCN1CCN(C2=Nc3cc(Cl)ccc3Oc3ccccc32)CC1 | null | null | null |
668,659 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:32][CH2:31][C:26]4(OCC[O:27]4)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21]... | O=C(OCc1ccccc1)N1CCN(c2ccc(N3CCC4(CC3)OCCO4)cc2)CC1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 90 | 7 | To a solution of 4-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]piperazine-1-carboxylic acid benzyl ester (30 g) in 1,4-dioxane (450 ml) was added 1N-hydrochloric acid (240 ml) at ambient temperature, and the mixture was stirred for 7 hours at 90° C. The reaction mixture was poured into water. The mixture was adjuste... | O=C1CCN(c2ccc(N3CCN(C(=O)OCc4ccccc4)CC3)cc2)CC1 | null | 78.7 | null |
1,752,677 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [CH3:1][CH2:2][N:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([NH:33][S:34]([C:37]5[CH:42]=[CH:41][C:40]([NH:43][C@@H:44]([CH2:54][S:55][C:56]6[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=6)[CH2:45][CH2:46][... | CCn1c(C)c(C(=O)O)c(-c2cccc(N3CCN(c4ccc(NS(=O)(=O)c5ccc(N[C@H](CCN6CCC(O)CC6)CSc6ccccc6)c(S(=O)(=O)C(F)(F)F)c5)cc4)CC3)c2)c1-c1ccc(Cl)cc1 | CC(C)(C)OC(=O)C1CCC(O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 7 was prepared from BM-957 and tert-butyl 4-hydroxycyclohexanecarboxylate according general procedure IV. MS (ESI): m/z 1192.25 (M+H)+. | CCn1c(C)c(C(=O)OC2CCC(C(=O)O)CC2)c(-c2cccc(N3CCN(c4ccc(NS(=O)(=O)c5ccc(N[C@H](CCN6CCC(O)CC6)CSc6ccccc6)c(S(=O)(=O)C(F)(F)F)c5)cc4)CC3)c2)c1-c1ccc(Cl)cc1 | null | null | null |
236,449 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-:22])=O)[C:5]([NH:12][C:13]([C:15](OCC)=[O:16])=[O:14])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C)C=O.N.[H][H]>O1CCCC1.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:12][C:13](=[O:14])[C:15](=[O:16])[N:20]2[OH:22])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1 | [H][H] | CCOC(=O)C(=O)Nc1c([N+](=O)[O-])cc(Cl)cc1C(F)(F)F | null | [Pt] | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | To a solution of 1.0 g (2.94 mmol) 5-chloro-2-ethoxalylamino-3-nitrobenzotrifluoride in 75 ml tetrahydrofuran was added 25 ml dimethylformamide and 1.0 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 100 mg 5% Pt-C as a catalyst. When the hydrogen uptake was completed, the catalyst was fi... | O=c1[nH]c2c(C(F)(F)F)cc(Cl)cc2n(O)c1=O | null | 80 | null |
183,996 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14]C(C)C)=[CH:9][C:8]=1[N:18]1[C:22](=[O:23])[N:21]([CH2:24][F:25])[C:20]([CH3:26])=[N:19]1>>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([OH:14])=[CH:9][C:8]=1[N:18]1[C:22](=[O:23])[N:21]([CH2:24][F:25])[C:20]([CH3:26])=[N:19]1 | Cc1nn(-c2cc(OC(C)C)c(Cl)cc2Cl)c(=O)n1CF | null | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | 2.5 | To 5 mL of stirring concentrated sulfuric acid was added portionwise 0.53 g (0.0016 mole) of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-4-fluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one. After complete addition, the mixture was stirred at room temperature for 2.5 hours. The mixture was poured into 100 mL of ic... | Cc1nn(-c2cc(O)c(Cl)cc2Cl)c(=O)n1CF | null | 72.8 | null |
428,864 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][CH:18]=[C:19]([CH2:21]Cl)[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:25]([NH:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][... | CC(C)NC(C)C | CN1Cc2c(-c3nc(CCl)co3)ncn2-c2cccc(Cl)c2C1=O | 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 | null | 0.30 g (0.00082 mol) of 7-chloro-3-(4-chloromethyl-oxazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one was dissolved in 40 ml of tetrahydrofuran, treated with 2.3 ml (0.0165 mol) of diisopropylamine and boiled at 150° in an autoclave for 20 hrs. The solution was completely freed from the solven... | CC(C)N(Cc1coc(-c2ncn3c2CN(C)C(=O)c2c(Cl)cccc2-3)n1)C(C)C | null | 31.3 | null |
1,464,484 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=2)=[C:6]([C:16]#[N:17])[C:5]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])(=[O:3])[CH3:2].OI(C1C=CC=CC=1)[O:28][S:29]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(#N)C>>[CH3:36][C:35]1[CH:34]=[CH:33][... | Cc1ccc(S(=O)(=O)OI(O)c2ccccc2)cc1 | CC(=O)c1sc(-c2ccnc(F)c2)c(C#N)c1-c1ccc(Cl)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 90 | null | A mixture of 5-acetyl-4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)thiophene-3-carbonitrile (0.48 g, 1.2 mmol) and [hydroxy(tosyloxy)iodo]benzene (0.819 g, 2.09 mmol) in ACN (20 mL, 400 mmol) was heated at 90° C. overnight. The mixture was cooled down to rt. The solvent was evaporated and the residue was purified by ... | Cc1ccc(S(=O)(=O)OCC(=O)c2sc(-c3ccnc(F)c3)c(C#N)c2-c2ccc(Cl)cc2Cl)cc1 | null | 46 | null |
1,615,235 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Cl.[C:2]1([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C1COCC1.C(OCC)(=O)C>[C:8]([CH:10]1[CH2:15][CH2:14][N:13]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[... | O=C(c1ccccc1)C1CCNCC1 | O=C(Cl)OCc1ccccc1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirring suspension of phenyl(piperidin-4-yl)methanone hydrochloride 86 (1.97 g, 8.73 mmol) and potassium carbonate (3.62 g, 26.2 mmol) in THF (40 mL) at 0° C. was added benzyl chloroformate (1.433 mL, 10.04 mmol) and the reaction mixture was allowed to slowly warm to room temperature and stirred for 2 h. The mixt... | O=C(c1ccccc1)C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | null |
27,213 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | [CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[C:20]2[S:24][C:23]([CH3:25])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>C1C=CC=CC=1>[CH3:25][C:23]1[S:24][C:20]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:14][CH:15]=2)=[O:26])=[CH:21][CH:22]... | CCOC(=O)C(C)(C(=O)OCC)c1ccc(C(=O)c2ccc(C)s2)cc1 | null | null | Cl | [Na+] | [OH-] | 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 | 0.17 | A mixture of 15.5 parts of diethyl 2-methyl-2-[p-(5-methyl-2-thenoyl)phenyl]malonate and 120 parts of sodium hydroxide solution 5% is stirred and refluxed for 5 hours. The reaction mixture is cooled and shaken twice with 80 parts of benzene. The aqueous phase is acidified with concentrated hydrochloric acid solution. A... | Cc1ccc(C(=O)c2ccc(C(C)C(=O)O)cc2)s1 | null | null | null |
1,493,964 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([F:14])[CH:3]=1.O=S(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]2[C:5]([CH2:9][CH2:10][C:11]2=[O:13])=[C:4]([F:14])[CH:3]=1 | Cc1cc(CCC(=O)O)c(F)cc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 3-(4-bromo-2-fluoro-5-methylphenyl)propanoic acid (EP1795524 A1; 8.4 g) in DCM (200 mL) was added SOCl2 (19.1 g) dropwise at r.t. The mixture was stirred for 2 hours at r.t. The solvent was removed under reduced pressure. AlCl3 (21.4 g) was added to the residue. The brown slurry was heated to 130° C. f... | Cc1c(Br)cc(F)c2c1C(=O)CC2 | null | null | null |
1,651,797 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2].CC([O-])(C)C.[K+].Cl[NH2:19]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:19])[CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2] | NCl | CCOC(=O)c1cc(F)c[nH]1 | null | CC(C)(C)[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 | 1.5 | To a solution of 4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester (1.57 g, 10.0 mmol) in 20 ml DMF is added potassium tert-butylate (2.24 g, 20.0 mmol) under nitrogen. After stirring at room temperature for 90 minutes, the chloroamine solution from above (110 ml, ca. 25 mmol) is added slowly, after which the mixture i... | CCOC(=O)c1cc(F)cn1N | null | null | null |
401,128 | ord_dataset-7fed188163cf4ccca934ec71504c7f8a | null | 1998-01-01T00:05:00 | true | [CH2:1]([C:3]1[N:8]2[N:9]=[CH:10][N:11]=[C:7]2[N:6]=[CH:5][CH:4]=1)[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH:1]([C:3]1[N:8]2[N:9]=[CH:10][N:11]=[C:7]2[N:6]=[CH:5][CH:4]=1)[CH3:2] | CCc1ccnc2ncnn12 | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 7-ethyl-1,2,4-triazolo[1,5-a]pyrimidine (10.5 g), N-bromosuccinimide (12.63 g), dibenzoylperoxide (0.3 g) and tetrachloromethane (270 ml) was heated under reflux for 5 hours with stirring. The mixture was filtered and a crude product was obtained by evaporation of the solvent from the filtrate. This was pu... | CC(Br)c1ccnc2ncnn12 | null | null | null |
459,010 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[CH2:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19] | CCCCCCCCBr | c1ccc2[nH]ccc2c1 | null | C1COCCOCCOCCOCCOCCO1 | [K+] | [OH-] | 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 | 2 | A mixture of indole (1) (0.03 mole, 3.51 g), potassium hydroxide (0.03 mole, 1.97 g) powdered in a mortar, and 18-crown-6 ether (0.001 mole, 250 mg) in benzene (20 cm3) is heated under reflux with vigorous stirring for two hours. A solution of octylbromide (2a), (0.04 mole, 7.72 g) in benzene (10 cm3) is added and refl... | CCCCCCCCn1ccc2ccccc21 | null | 72.3 | null |
1,662,199 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[Cu][C:11]#[N:12].[C-]#N.[Na+].CN(C)C=O>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[N:12])=[N:4][C:3]=1[CH3:9] | N#C[Cu] | Cc1nc(Br)ccc1Br | null | [C-]#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CN(C)C=O | null | null | null | null | null | null | null | null | null | 95 | 48 | A 1-L, three-neck, round-bottom flask equipped with a mechanical stirrer and a nitrogen inlet was charged with 3,6-dibromo-2-methylpyridine (150 g, 0.59 mol), copper (I) cyanide (42.8 g, 0.47 mol) and sodium cyanide (23 g, 0.47 mol). To the mixture was added N,N-dimethylformamide (300 mL). The mixture was heated to 95°... | Cc1nc(C#N)ccc1Br | null | 66.4 | null |
1,009,662 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | O[CH:2]([C:19]1[CH:24]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29][CH2:30][CH3:31])=[C:21]([F:32])[C:20]=1[C:33]([F:36])([F:35])[F:34])[CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl.[Na]>C1(C)C=CC... | CCCC1CCC(C2CCC(CC(O)c3cc([Si](C)(C)C)c(OCC)c(F)c3C(F)(F)F)CC2)CC1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | Cl | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | 20.7 g of the crude 1-hydroxy-1-(2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilylphenyl)-2-(4-(4-propylcyclohexyl)cyclohexyl)ethane obtained in the first step was dissolved in toluene. 0.68 g (3.57 mmol) of p-toluene sulfonic acid monohydrate was added and refluxed under heating for 2 hours while dewatering by usin... | CCCC1CCC(C2CCC(C=Cc3cc([Si](C)(C)C)c(OCC)c(F)c3C(F)(F)F)CC2)CC1 | null | 80.2 | null |
1,742,017 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][C:17]=2[CH2:25][O:26][CH2:27][C:28](Cl)=[O:29])=[CH:10][CH:9]=1.O>ClCCl>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:... | O=C(Cl)COCc1nc2ccccn2c1C#Cc1ccc(F)cc1 | C1COCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.806 ml (9.25 mmol) of morpholine were solubilised in 4 ml of dichloromethane with magnetic stirring, a solution of 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)acetyl chloride in 4 ml of dichloromethane was added and then the mixture was added at r.t. for 1 h before being treated with 10 ml of wa... | O=C(COCc1nc2ccccn2c1C#Cc1ccc(F)cc1)N1CCOCC1 | null | 58 | null |
1,119,343 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | C([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[N:24](CC[Si](C)(C)C)[C:23](=[O:34])[CH2:22]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([F:20])([F:18])[F:19])[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27]... | C[Si](C)(C)CCN1C(=O)CN(c2ccc(CCC(F)(F)F)cc2OCc2ccccc2)S1(=O)=O | null | null | [Pd+2] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound is prepared from 5-[2-benzyloxy-4-(3,3,3-trifluoropropyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one analogous to Example 292, steps B and C with the modification that Pd(OH)2 is used as the catalyst in the reduction step: (M−1)−=323. | O=C1CN(c2ccc(CCC(F)(F)F)cc2O)S(=O)(=O)N1 | null | null | null |
763,585 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH3:1][C:2]([CH3:13])([CH3:12])[CH2:3][C:4]1(C=C)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1.CC[O:16][C:17](C)=[O:18]>O>[CH3:13][C:2]([CH3:1])([CH3:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:17]([OH:18])=[O:16])=[CH:8][CH:9]=1 | CCOC(C)=O | C=CC1(CC(C)(C)C)C=CC=CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 40 | 16 | To a solution of 1.74 g (7.76 mmol) of 4-(2,2-dimethylpropyl)-4-ethenylbenzene (from Step A) in 10 mL EtOAc and 10 mL H2O was added 8.30 g (38.8 mmol) of NaIO4 and 1 mg (0.0078 mmol) RuO2. The reaction mixture was heated to 40° C. for 30 min. The reaction mixture was cooled and stirred at rt for 16 hr. To the reaction ... | CC(C)(C)Cc1ccc(C(=O)O)cc1 | null | null | null |
919,473 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH2:31][CH2:32]Cl)(=[O:29])=[O:28])[CH2:23][CH2:22]2)[N:3]=1.[NH2:34][C@@H:35]([CH3:38])[CH2:36][OH:37]>>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:1... | C[C@H](N)CO | COc1ccc(F)c(F)c1C(=O)c1cnc(NC2CCN(S(=O)(=O)CCCCl)CC2)nc1N | null | null | null | null | null | null | null | 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 was prepared from [4-amino-2-[1-(3-chloro-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (Example 226) and (S)-(+)-2-amino-1-propanol (Aldrich) in an analogous manner as described in Example 227. HR-MS (ES, m/z) calculated for C23H33N6O5SF2[(M+H)+] 543.21... | COc1ccc(F)c(F)c1C(=O)c1cnc(NC2CCN(S(=O)(=O)CCCN[C@@H](C)CO)CC2)nc1N | null | null | null |
469,040 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:15][NH2:16]>>[CH3:15][NH:16][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1 | COC(=O)c1cnc(Cl)c([N+](=O)[O-])c1 | CN | null | null | null | null | null | 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 | null | 1.6 g (7.4 mMol) of methyl 6-chloro-5-nitro-nicotinate (see Bernie et al. in J. Chem. Soc. 1951, 2590) were stirred in 20 ml of 40% aqueous methylamine solution at room temperature for 30 minutes. The reaction mixture was then diluted with ice water, the yellow precipitate formed was filtered off and dried. Yield: 1.2 ... | CNc1ncc(C(=O)OC)cc1[N+](=O)[O-] | null | null | null |
148,913 | ord_dataset-0b70410902ae4139bd5d334881938f69 | null | 1986-01-01T00:09:00 | true | [O:1]=[C:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][NH:3]1)=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[C:10]=3[Cl:18].[OH-:19].[K+].Cl>C(O)C.O>[NH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[C:2]([OH:19])=[O:1] | [OH-] | COc1cc2c3c([nH]c2c(Cl)c1Cl)C(=O)NCC3 | null | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | The above lactam was hydrolyzed with base according to the following procedure: 5 g of 1-oxo-6-methoxy-7,8-dichloro-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole were dissolved in a mixture of 77 ml of ethanol and 51 ml of water. 13.9 g of potassium hydroxide were added, and the solution was heated to refluxing temperature... | COc1cc2c(CCN)c(C(=O)O)[nH]c2c(Cl)c1Cl | null | 96.9 | null |
514,094 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [CH2:1]([N:9]=[C:10]=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[OH:22]>C1(C)C=CC=CC=1>[C:3]1([CH2:2][CH2:1][NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=2[OH:22])=[O:11])[CH:8]=[CH:7][CH:6... | O=C=NCCc1ccccc1 | Nc1ccc([N+](=O)[O-])cc1O | 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 | 80 | 24 | To a solution of phenethyl isocyanate (382 mg, 2.6 mmol) in toluene, 2-amino-5-nitrophenol (400 mg, 2.6 mmol) was added. The reaction mixture was stirred at 80° C. for 24 hours, then cooled to room temperature. The product was purified by precipitation from toluene and filtering (650 mg, 83%). m.p: 188.6-189.4° C.; EI-... | O=C(NCCc1ccccc1)Nc1ccc([N+](=O)[O-])cc1O | null | null | null |
351,413 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:21]=[... | Cc1oc(-c2ccccc2)nc1CCl | CC(=O)c1ccc(O)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 2.5 | A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (9.2 g), p-hydroxyacetophenone (7.95 g), potassium carbonate (6.73 g) and N,N-dimethylformamide (DMF) (100 ml) was stirred for 2.5 hours at temperatures ranging from 70° to 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl ... | CC(=O)c1ccc(OCc2nc(-c3ccccc3)oc2C)cc1 | null | 85.2 | null |
1,120,471 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:22]=[C:21]3[C:13]([C:14]4[C:15](B5OC(C)(C)C(C)(C)O5)=[CH:16][CH:17]=[C:18]([C:23]([NH2:25])=[O:24])[C:19]=4[NH:20]3)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.Br[C:36]1[CH:45]=[CH:44][CH:43]=[C:42]2[C:37]=1[CH:38]=[CH:39][CH:40]=[C:41]2[NH2:46].C(=O)([O-])[O-].[K+].[K+]>C... | CN1CCN(C(=O)c2ccc3c(c2)[nH]c2c(C(N)=O)ccc(B4OC(C)(C)C(C)(C)O4)c23)CC1 | Nc1cccc2c(Br)cccc12 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 90 | null | Step 2 A mixture of 7-(4-methylpiperazine-1-carbonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1-carboxamide (the crude product prepared according to Step 1, 40 mg, 0.065 mmol), 5-bromonaphthalen-1-amine (21.61 mg, 0.097 mmol), and potassium carbonate (13.45 mg, 0.097 mmol) in toluene (1.5 mL) and e... | CN1CCN(C(=O)c2ccc3c(c2)[nH]c2c(C(N)=O)ccc(-c4cccc5c(N)cccc45)c23)CC1 | null | 42 | null |
1,436,253 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][O:15][C:16]2[N:17]=[CH:18][C:19]([C:22]([OH:24])=O)=[N:20][CH:21]=2)=[CH:4][CH:3]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[O:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:22]([C:19]2[CH:18]=[N:17][C:16]([O:15][CH2:14][C:9]3[N:10... | Cn1nnc(-c2ccc(F)cc2)c1COc1cnc(C(=O)O)cn1 | NC1CCOCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | As described for example 53c, 5-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid (96 mg, 0.29 mmol) was converted, using 4-aminotetrahydropyran instead of isopropylamine, to the title compound (74 mg, 62%) which was obtained as an off white solid. MS: m/e=413.4 [M+H]+. | Cn1nnc(-c2ccc(F)cc2)c1COc1cnc(C(=O)NC2CCOCC2)cn1 | null | 62 | null |
889,311 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [OH-:1].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[C:9](=O)[N:8]([C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([NH2:22])=[O:21])[C:7]2=[O:23]>C1COCC1.CO>[Cl:13][C:12]1[C:4]([Cl:3])=[CH:5][C:6]([C:7]([OH:23])=[O:1])=[C:10]([C:9]2[NH:22][C:20](=[O:21])[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[N:8]=2)[CH:11]=1 | NC(=O)c1sccc1N1C(=O)c2cc(Cl)c(Cl)cc2C1=O | [OH-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 80 | 2.5 | 3-aminothiophene-2-carboxamide was added to an acetic acid solution of 4,5-dichlorophthalic anhydride and stirred all night heated to reflux to give 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide. 1M NaOH aq was added to THF-MeOH solution of the obtained 3-(5,6-dichloro-1,3-dioxo-1,3-di... | O=C(O)c1cc(Cl)c(Cl)cc1-c1nc2ccsc2c(=O)[nH]1 | null | null | null |
508,375 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [CH:1]1([C:4]2[CH:5]=[C:6]([C:18]#[C:19][Si](C)(C)C)[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]3([CH3:17])[CH3:16])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]#[CH:19])[CH:7]=[C:8]3[C:13]=2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]3([CH3:17])[CH3:16])[CH2:3][C... | CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)cc(C3CC3)c2O1 | 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 | Following general procedure E and using 8-cyclopropyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman (Intermediate 33, 0.17 g, 0.68 mmol), methanol and potassium carbonate (0.2 g, 1.47 mmol) the title compound was obtained as an oil (0.064 g, 47%). | C#Cc1cc(C2CC2)c2c(c1)C(C)(C)CC(C)(C)O2 | null | null | null |
551,367 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [CH2:1]([NH:3][C:4](=[O:16])[C:5]1[C:10]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[I:15])[CH3:2].[CH2:17](N)C#C>>[I:15][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]=1[C:4]([NH:3][CH2:1][C:2]#[CH:17])=[O:16] | C#CCN | CCNC(=O)c1c(I)cccc1[Si](C)(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 | The acid chloride prepared in Example 207 was reacted with propargylamine (3 eq) using General Method E1 to afford the title compound. Purification by recrystallization from hexanes gave 0.48 g of the title compound as an off-white solid in 85% yield. m.p. 109-111° C. | C#CCNC(=O)c1c(I)cccc1[Si](C)(C)C | null | 85 | null |
25,472 | ord_dataset-2ada3fda46fc44719ba0c8001f53c1b3 | null | 1977-01-01T00:06:00 | true | CSC(SC)=[C:4]([C:7]#N)[C:5]#[N:6].CS[C:13](SC)=[C:14]([C:23]#[N:24])[C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16]>C(O)C>[O:16]1[C:15]2[CH:14]=[CH:13][CH:7]=[CH:4][C:5]=2[NH:6][C:13]1=[C:14]([C:23]#[N:24])[C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16] | CSC(SC)=C(C#N)C(=O)N1CCOCC1 | CSC(SC)=C(C#N)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 | null | null | The procedure described in Example 1 is repeated using, instead of 3,3-bis(methylthio)-2-cyanoacrylonitrile, an equivalent amount of 3,3-bis(methylthio)-2-cyanoacrylic acid morpholide and holding the mixture under reflux for 24 hours to obtain 2-benzoxazolinylidene-cyanoacetic acid morpholide of melting point 217°-219°... | N#CC(C(=O)N1CCOCC1)=C1Nc2ccccc2O1 | null | null | null |
757,321 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | C[O:2][C:3](=[O:23])[C@@H:4]([OH:22])[C@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1.[OH-].[Na+].CO>O1CCOCC1>[C:18]([O:17][C:15]([NH:14][C@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C@H:4]([OH:22])[C:3]([OH:23])=[O:2])... | COC(=O)[C@@H](O)[C@@H](Cc1cccc(F)c1)NC(=O)OC(C)(C)C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 1.5 | A mixture of (2S,3R)-3-tert-Butoxycarbonylamino-4-(3-fluoro-phenyl)-2-hydroxy-butyric acid methyl ester (3.28 g, 10.05 mmol, 1 eq), 4N NaOH (4 mL, 16 mmol, 1.6 eq), MeOH (42 mL) and 1,4-dioxane (63 mL) was stirred at ambient temperature for 1.5 h after which the solvents were evaporated. To the residue was added 10% ci... | CC(C)(C)OC(=O)N[C@H](Cc1cccc(F)c1)[C@H](O)C(=O)O | null | 97.2 | null |
1,326,455 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[N:11]\[S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13].C1COCC1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[NH:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13] | CC(C)(C)[S@](=O)/N=C1\CCc2c(Br)cccc21 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 0.5 | To a stirred suspension of crude (S,E)-N-(4-bromo-2,3-dihydro-1H-inden-1-ylidene)-2-methylpropane-2-sulfinamide IND INT-9 in toluene (250 mL) under N2 was added anhydrous THF (250 mL) and the reaction mixture was cooled to −78° C. Sodium borohydride (26.8 g, 710 mmol) was added in four portions over 30 min (internal te... | CC(C)(C)[S@](=O)N[C@H]1CCc2c(Br)cccc21 | null | 61 | null |
3,517 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:11]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[O:12])... | COc1ccc(N)cc1 | O=C(Cl)C12CC3CC(CC(C3)C1)C2 | 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 | null | null | Subject 6.5 g. (33.0 mmoles) of 1-adamantane carboxylic acid chloride, 4.0 g. (33.0 mmoles) of p-anisidine and 10.0 ml. of triethylamine to the process of Example 11 and crystallize the residue obtained thereby from chloroform to yield the title product, m.p. 181°-184°C. | COc1ccc(NC(=O)C23CC4CC(CC(C4)C2)C3)cc1 | null | null | null |
1,331,220 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][S:14]2)=[CH:9][CH:8]=1.O>CN(C=O)C>[N:1]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[CH:16]=[CH:15][S:14]2)=[CH:11][CH:12]=1)=[N+:2]=[N-:3] | [N-]=[N+]=[N-] | O=c1ccsn1-c1ccc(CBr)cc1 | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 20 | Sodium azide (6.0 mg, 0.0923 mmol) was added to a solution of 2-(4-bromomethylphenyl)isothiazol-3-one 31 (18.2 mg, 0.0674 mmol) in DMF (1 mL) and stirred for 20 h at room temperature. Water (10 mL) was added and the mixture was extracted with diethyl ether. The combined organic layer was dried (MgSO4), filtered and eva... | [N-]=[N+]=NCc1ccc(-n2sccc2=O)cc1 | null | 74.7 | null |
227,337 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)(O)[CH:9]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2... | CCOC(=O)C(C(C)(C)C)C(O)(c1ccc(F)cc1)c1ccc(F)cc1 | null | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 3,3-bis(4-fluorophenyl)-3-hydroxy-2-(1,1-dimethylethyl)propionate (1.0 g, 2.8 mmol) and p-toluenesulfonic acid (0.3 g) in 20 mL toluene was heated at reflux for 45 minutes. The mixture was cooled and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 1% ethyl ace... | CCOC(=O)C(=C(c1ccc(F)cc1)c1ccc(F)cc1)C(C)(C)C | null | 36.3 | null |
562,770 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [Br:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:26])=[C:8]([CH3:25])[C:9]=1[C:10]([C:12]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]([OH:21])=[C:14]([CH:22]([CH3:24])[CH3:23])[CH:13]=1)=[O:11].Cl[S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[C:37]([OH:44])[CH:36]=1)(=[O:3... | O=C(O)c1ccc(S(=O)(=O)Cl)cc1O | Cc1oc(Cc2ccccc2Br)c(C(=O)c2cc(C(C)C)c(O)c(C(C)C)c2)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 | The title compound was prepared according to the procedure in Example 4 using [2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (0.300 g, 0.639 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.197 g, 0.831 mmol). Purification on Dynamax C18 (90% CH3CN/H2O) gave 0.20 g (47%) o... | Cc1oc(Cc2ccccc2Br)c(C(=O)c2cc(C(C)C)c(OS(=O)(=O)c3ccc(C(=O)O)c(O)c3)c(C(C)C)c2)c1C | null | 46.7 | null |
1,178,741 | ord_dataset-0f9d2dbe929a45c3892ae75e81e99443 | null | 2012-01-01T00:06:00 | true | CS([C:4]1[N:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:14]=[N:13][N:12]([CH3:15])[C:11]=2[NH:16][C:17]2[CH:18]=[C:19]([NH:24][C:25](=[O:36])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH:20]=[CH:21][C:22]=2[CH3:23])[CH:5]=1)=O.[N:37]1([CH2:43][CH2:44][NH2:45])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]... | NCCN1CCOCC1 | Cc1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1Nc1c(-c2cc(S(C)=O)ncn2)cnn1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 80 | null | The mixture of N-{3-[4-(6-Methanesulfinyl-pyrimidin-4-yl)-2-methyl-2H-pyrazol-3-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide (40 mg, 0.078 mmol) and 2-Morpholin-4-yl-ethylamine (100 μL) in 2-propanol is heated to 80° C. for 3 hours. The reaction mixture is cooled to room temperature and concentrated. The crude... | Cc1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1Nc1c(-c2cc(NCCN3CCOCC3)ncn2)cnn1C | null | null | null |
677,734 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | [CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:15]([C:16](=[O:18])[CH3:17])=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26]... | COC(OC)N(C)C | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(C)=O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of 1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (5.56 g, 15.9 mmol) in N,N-dimethylformamide dimethyl acetal (25 mL) was heated at reflux for 5 days. The mixture was allowed to cool to room temperature. Water was added and the resulting mixture was extracted with ethyl acet... | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(=O)/C=C/N(C)C)cc1 | null | 93 | null |
1,195,755 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[Cu][C:16]#[N:17]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:7]1[C:2]([C:16]#[N:17])=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9] | O=[N+]([O-])c1cc(C(F)(F)F)cnc1Br | N#C[Cu] | null | CCCC[N+](CCCC)(CCCC)CCCC | [Br-] | 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 | 25 | null | 2-Bromo-3-nitro-5-trifluoromethyl-pyridine (10.00 g, 36.87 mmol) was dissolved in toluene (250 ml) with stirring to give a pale yellow solution. Tetrabutylammonium bromide (11.90 g, 36.9 mmol) was added followed by copper(I) cyanide (9.92 g, 111 mmol) and the mixture was heated at reflux for 10 h. After cooling to RT, ... | N#Cc1ncc(C(F)(F)F)cc1[N+](=O)[O-] | null | null | null |
759,281 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | Cl[C:2]1[C:3]2[N:4]([C:8]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[N:21]=3)=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[CH:27]1([NH:26][C:22]2[N:21]=[C:20]([C:8]... | C1COCCN1 | O=[N+]([O-])c1cccc(-c2nc3c(Cl)cccn3c2-c2ccnc(NC3CCCC3)n2)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 | 150 | null | A thick walled glass tube was charged with N-{4-[8-chloro-2-(3-nitrophenyl)imidazo[1,2-α]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (44 mg, 0.10 mmol) and morpholine (4 mL). The vessel was sealed and heated to 150° C. for 4 days. The mixture was concentrated in vacuo and purified via flash chromatography on silica... | O=[N+]([O-])c1cccc(-c2nc3c(N4CCOCC4)cccn3c2-c2ccnc(NC3CCCC3)n2)c1 | null | 6 | null |
557,086 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:12]2[CH:25]=[C:24]([CH2:26][CH3:27])[S:23][C:13]=2[N:14]=[C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:16]=1>>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:15]2[N:16]=[C:11]([NH:9][CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:12... | CCc1cc2c(Cl)nc(-c3cccnc3)nc2s1 | NCCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | With the procedure of Example 1, the reaction of phenethylamine with 4-chloro-2-(pyridin-3-yl)-6-ethyl-thieno-[2,3-d]-pyrimidine yields 2-(pyridin-3-yl)-4-phenethylamino-6-ethyl-thieno-[2,3-d]-pyrimidine. | CCc1cc2c(NCCc3ccccc3)nc(-c3cccnc3)nc2s1 | null | null | null |
548,202 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [NH2:1][C:2]1[N:3]=[N:4][N:5]([CH2:7][CH2:8][CH3:9])[N:6]=1.[CH:10]1[C:23]2[CH:22]([C:24](Cl)=[O:25])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>>[CH2:7]([N:5]1[N:4]=[N:3][C:2]([NH:1][C:24]([CH:22]2[C:23]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[O:15][C:16]3[C:21]2=[CH:20][CH:19]... | CCCn1nnc(N)n1 | O=C(Cl)C1c2ccccc2Oc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid,, m.p. 208-209° and MS: (neg. ions): m/e=334.1 (M+−H) was prepared in accordance with the general method of example 1 from 5-amino-2-propyl-2H-tetrazole and 9H-xanthene-9-carbonyl chloride. | CCCn1nnc(NC(=O)C2c3ccccc3Oc3ccccc32)n1 | null | null | null |
263,972 | ord_dataset-a7bd0db0684c464bb02ff6a36065fee3 | null | 1993-01-01T00:03:00 | true | [CH2:1]1[C:10](=O)[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(N)CN.[N+:16]([CH3:19])([O-:18])=[O:17]>>[N+:16]([CH2:19][C:10]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:9]=1)([O-:18])=[O:17] | C[N+](=O)[O-] | O=C1CCc2ccccc2C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NCCN | null | null | null | null | null | null | null | null | null | null | null | null | A solution of β-tetralone (Aldrich Chemical Co., Milwaukee, Wis. 53233) (24.5 gm) and ethylenediamine (1.75 gm) in nitromethane (250 ml) was heated at 80° for 16 hours. The reaction mixture was filtered, and the filtrate was evaporated to give a red oil. This was partially purified by elution through a short silica col... | O=[N+]([O-])CC1=Cc2ccccc2CC1 | null | null | null |
590,287 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([NH2:19])[CH3:18]>>[CH2:17]([NH:19][C:8](=[O:9])[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:18] | O=C(Cl)C(c1ccccc1)c1ccccc1 | CCN | null | null | null | null | null | null | null | 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, off-white solid, m.p. 87° C. and MS: m/e=239 (M+) was prepared in accordance with the general method of example 1 from diphenylacetyl chloride and ethylamine. | CCNC(=O)C(c1ccccc1)c1ccccc1 | null | null | null |
2,870 | ord_dataset-15ce1bcfb62046d9bec87d32620888d5 | null | 1976-01-01T00:03:00 | true | [ClH:1].[CH2:2]([C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:22]=[C:21]([O:23]C)[CH:20]=[C:19]([O:25]C)[CH:18]=2)=[O:16])[CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.N>>[ClH:1].[CH2:2]([C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([OH:25])[CH:18]=2)=[O:16])[CH:12]=[CH:11][CH:1... | COc1cc(OC)cc(C(=O)c2cccc(Cc3ccccc3)n2)c1 | null | null | Br | Cl | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | About 15.5 g. of 3,5-dimethoxyphenyl 6-benzyl-2-pyridyl ketone hydrochloride in 55 ml. of constant boiling hydrobromic acid were heated under reflux for 12 hours. Removal of the solvent gave a tacky residue which was basified with ammonia solution and was extracted three times with a total of 90 ml. of boiling ethyl ac... | O=C(c1cc(O)cc(O)c1)c1cccc(Cc2ccccc2)n1 | null | null | null |
1,675,049 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[NH2:11][C:12]1[N:17]=[CH:16][C:15]2[C:18]([CH3:26])([CH3:25])[C:19](=[O:24])[N:20]([CH:21]3[CH2:23][CH2:22]3)[C:14]=2[CH:13]=1>>[CH:21]1([N:20]2[C:14]3[CH:13]=[C:12]([NH:11][C:8]([C:5]4[CH:6]=[N:7][C:2]([CH3:1])=[N:3][CH:4]=4)=[O:10])[N:17]=[CH:16][C:15]=3... | Cc1ncc(C(=O)O)cn1 | CC1(C)C(=O)N(C2CC2)c2cc(N)ncc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to example 26 from 2-methylpyrimidine-5-carboxylic acid and 6-amino-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (example 79c). The title compound was obtained as light yellow crystals. | Cc1ncc(C(=O)Nc2cc3c(cn2)C(C)(C)C(=O)N3C2CC2)cn1 | null | null | null |
234,804 | ord_dataset-45d20d09e4d64f45bdd419044025b4d3 | null | 1991-01-01T00:09:00 | true | Cl.[CH3:2][C:3]1[C:12]([CH2:13][CH2:14]Cl)=[C:11](Cl)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:19]=1[NH2:20]>CC(O)C>[CH3:17][C:18]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:19]=1[N:20]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([CH3:2])[C:... | Cc1cccc(C)c1N | Cc1nc2ccccc2c(Cl)c1CCCl | null | Cl | 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 | null | null | A mixture of 2-methyl-3-(2-chloroethyl)-4-chloroquinoline hydrochloride (13.8 g, 50 mmol), 2,6-dimethylaniline (12.5 ml, 100 mmol) and 2-propanol (400 ml) was heated to 140° for 5 days in a pressure vessel, then cooled and evaporated. The crude product was converted to free base and chromatographed (silica gel, methano... | Cc1cccc(C)c1N1CCc2c(C)nc3ccccc3c21 | null | 10.5 | null |
1,432,076 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | [CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([OH:19])=[CH:16]2)=[CH:11][C:10]=1[C:20]1[N:21]=[N:22][C:23]([N:26]([CH3:37])[CH:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[NH:30][C:29]([CH3:36])([CH3:35])[CH2:28]2)=[CH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:38]N1C(=O)CCC1=O>CN(C=O)C>[CH2:1... | O=C1CCC(=O)N1Cl | CN(c1ccc(-c2cc3ccc(O)cc3cc2OCc2ccccc2)nn1)C1CC(C)(C)NC(C)(C)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 8 | To a reaction mixture of 7-(benzyloxy)-6-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)naphthalen-2-ol (100 mg, 0.201 mmol) in DMF (2 mL) was added N-chlorosuccinimide (32.3 mg, 0.242 mmol) at room temperature. The reaction mixture was stirred overnight then loaded onto an SCX column, washed with Me... | CN(c1ccc(-c2cc3ccc(O)c(Cl)c3cc2OCc2ccccc2)nn1)C1CC(C)(C)NC(C)(C)C1 | null | null | null |
437,965 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:14][CH2:13]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:15]1[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][NH2:8])[CH2:17][CH2:16]1 | CC(C)(C)OC(=O)NCCCN1CCC(c2ccccn2)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 | 1 | To 1-Benzyl-4-(2-pyridyl)-piperidine (3.26 g, 12.9 mmol) in dry methanol (25 ml), 10% palladium hydroxide (1.9 g) was added and the solution was hydrogenated at 200 psi for 24 hours. The solution was filtered over celite, concentrated to give 2.1 g (99%) of 4-(2-pyridyl)-piperidine which was used as such for the subseq... | NCCCN1CCC(c2ccccn2)CC1 | null | 99.3 | null |
1,169,987 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | C([NH:5][S:6]([C:9]1[S:13][C:12]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH:22]=[C:21]([CH3:32])[N:20]=3)[CH:18]=2)=[N:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[CH:22]=[C:21]([CH3:32])[N:20]=[C:... | Cc1cc(-c2ccc(Cl)cc2)nc(-n2cnc(-c3ncc(S(=O)(=O)NC(C)(C)C)s3)c2)n1 | 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 | 25 | 15 | To a cooled and stirred solution of N-tert-butyl-2-{1-[4-(4-chloro-phenyl)-6-methyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiazole-5-sulfonamide (0.1 g) in dichloromethane (2 mL) was added TFA (2 mL) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness and purifie... | Cc1cc(-c2ccc(Cl)cc2)nc(-n2cnc(-c3ncc(S(N)(=O)=O)s3)c2)n1 | null | 18.1 | null |
1,407,944 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH3:13][C:14]1[N:18]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:17]2[CH2:25][CH2:26][O:27][CH2:28][C:16]=2[CH:15]=1.[N:29]1([S:34]([C:37]2[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1.C([SiH](CC)CC)C>C(Cl)Cl>[OH:27][CH2:26][CH2:... | O=Cc1ccc(S(=O)(=O)N2CCCC2)cc1 | CCOC(=O)Cn1c(C)cc2c1CCOC2 | null | CC[SiH](CC)CC | C[Si](C)(C)OS(=O)(=O)C(F)(F)F | 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 | 0 | 0.25 | To a flame-dried vial was charged with DCM (2 ml) and trimethylsilyl trifluoromethanesulfonate (0.081 ml, 0.448 mmol) was added at 0° C., followed by a solution of ethyl 2-(2-methyl-6,7-dihydropyrano[4,3-b]pyrrol-1(4H)-yl)acetate (50 mg, 0.224 mmol) and 4-(pyrrolidin-1-ylsulfonyl)benzaldehyde (53.6 mg, 0.224 mmol) in C... | CCOC(=O)Cn1c(C)c(Cc2ccc(S(=O)(=O)N3CCCC3)cc2)c(C)c1CCO | null | 33.9 | null |
27,644 | ord_dataset-14866e68bb5b47f5929457eecb4eb3a5 | null | 1977-01-01T00:07:00 | true | Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.C(Cl)(Cl)[Cl:13].S(Cl)(Cl)(=O)=O.[OH-].[Na+]>O>[Cl:13][C:6]1[S:2][C:3]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:11])[C:4]=2[CH:5]=1 | NC1CCCc2sccc21 | ClC(Cl)Cl | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(=O)(Cl)Cl | O | null | null | null | null | null | null | null | null | null | 25 | 3.5 | A sample of 11.4 grams 4,5,6,7-tetrahydrobenzo[b]-thiophen-4-amine hydrochloride is stirred in 150 ml. of chloroform at about 10° C., and 6.1 ml. of sulfuryl chloride is added dropwise. The mixture is stirred for 3.5 hours at room temperature, and then about 20 ml. of 50% sodium hydroxide solution is added gradually to... | NC1CCCc2sc(Cl)cc21 | null | null | null |
72,840 | ord_dataset-10f2568b472a4cabb35c3f313a159005 | null | 1980-01-01T00:11:00 | true | [Cl:1][C:2](Cl)([Cl:20])[CH:3]1[O:8][CH:7]([C:9](Cl)([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.CC(C)([O-])C.[K+]>CS(C)=O>[Cl:20][C:2]([Cl:1])=[C:3]1[O:8][C:7](=[C:9]([Cl:11])[Cl:10])[C:6]2[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1 | NC(=O)c1ccc2c(c1)C(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)O2 | null | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-carboxamide (3.14 g.) and potassium t-butoxide (2.5 g.) in 50% aqueous dimethylsulphoxide (50 ml.) was heated at 80°-90° C. for 2 hours. The solid product was filtered off, dried and crystallised from ethanol to give 2,4-bis(dichloromethylene)benzo[1,3]dioxin-6-ca... | NC(=O)c1ccc2c(c1)C(=C(Cl)Cl)OC(=C(Cl)Cl)O2 | null | null | null |
47,679 | ord_dataset-6d529f04a1724b5d85dcc290cf4c38bb | null | 1978-01-01T00:10:00 | true | [C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH:10]1[CH:14]([OH:15])[CH:13]=[CH:12][C:11]1=O)([OH:3])=[O:2].[OH-:17].[Na+]>>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[C:10]1[C:14](=[O:15])[CH2:13][CH:12]([OH:17])[CH:11]=1)([OH:3])=[O:2] | [OH-] | O=C(O)CCCC/C=C\C1C(=O)C=CC1O | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1.0mmole of all-cis-2-(6-carboxy-2-cis-hexenyl)-3,4-oxidocyclopentanone (Example 1106) and 3.0 mmoles of sodium carbonate in 15 ml. of water is allowed to stand at room temperature for 3 hours. The solution is acidified with HCl, saturated with sodium chloride, and extracted with ether. The extract is was... | O=C(O)CCCC/C=C\C1=CC(O)CC1=O | null | null | null |
697,849 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10]O)[CH2:5][CH2:4]1)=[O:2].[SH:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O.O>[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][S:12][C:13]2[NH:14][C:15]3[CH:21]=[CH:20][CH:19]=[C... | O=CN1CCN(CCO)CC1 | Sc1nc2ccccc2[nH]1 | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 containing 1-formyl-4-(2-hydroxyethyl)piperazine (1.58 g, 10 mmol), 2-mercaptobenzimidazole (5.56 g, 37 mmol), and triphenylphosphine (9.26 g, 35.3 mmol) in dimethylformamide (100 mL), diethyl azodicarboxylate (5.19 g, 29.8 mmol) was added dropwise over 5 minutes with ice-cooling and stirring under argon.... | O=CN1CCN(CCSc2nc3ccccc3[nH]2)CC1 | null | 75.4 | null |
955,433 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]C([O-])(C)C.[K+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:18])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | CC(C)(C)[O-] | O=C1CN(C(=O)OCc2ccccc2)CCN1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CI | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (2.00 g, 8.54 mmol) in DMF (30 mL) was added KOtBu (1.54 g, 13.7 mmol) under Ar. The resulting solution was stirred at room temperature for 15 min and cooled to 0° C. MeI (0.85 mL, 14 mmol) was then added dropwise. The reaction mixture was allowed to warm... | CN1CCN(C(=O)OCc2ccccc2)CC1=O | null | 66 | null |
845,420 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([CH3:32])[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=4[O:30][CH3:31])[C:15]=3[O:14]2)(=O)=O)=CC=1.[CH3:33][NH2:34]>>[CH3:31][O:30][C:23]1[C:24]([O:28][CH3:29])=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH:34]... | CN | COc1cccc(-c2cc(C)cc3c2OC(COS(=O)(=O)c2ccc(C)cc2)C3)c1OC | null | null | null | null | null | null | null | 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 (0.094 g, 44%) following the general procedure of Example 390 as a white solid, hydrochloride salt from (±)-[7-(2,3-dimethoxyphenyl) 5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.18 g, 0.40 mmol) and methylamine (0.123 g, 4.0 mmol). mp 85-89° C. | CNCC1Cc2cc(C)cc(-c3cccc(OC)c3OC)c2O1 | null | null | null |
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