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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
255,162 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[CH2:9][CH2:8]2 | CN1CCNCC1 | COc1cccc2c1CC(=O)CC2 | null | [BH3-]C#N | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 0.5 | 1.76 g (10 mmol) of 8-methoxy-2-tetralone, 3.00 g (30 mmol) of N-methylpiperazine and 1.80 g (30 mmol) of glacial acetic acid were refluxed in 30 ml of methanol for 4 hours. 1.30 g (20 mmol) of sodium cyanoborohydride were then added, and the mixture was refluxed for a further hour. The reaction mixture was substantial... | COc1cccc2c1CC(N1CCN(C)CC1)CC2 | null | 161.3 | null |
20,660 | ord_dataset-39f318aa6ec5450182abaf3662294306 | null | 1977-01-01T00:03:00 | true | ClCCC[O:5][P:6]1[CH2:10][CH:9]=[C:8]([CH3:11])[CH2:7]1.[CH2:12](O)[CH2:13][OH:14].C(Br)C>ClCCCl>[OH:14][CH2:13][CH2:12][P:6]1(=[O:5])[CH2:10][CH2:9][C:8]([CH3:11])=[CH:7]1 | CC1=CCP(OCCCCl)C1 | OCCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCBr | ClCCCl | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of 14.7 g. (0.076 mole) of 1-(chloropropoxy)-3-methyl-3-phospholene in 50 ml. of 1,2-dichloroethane was added, with stirring, over a period of 5 minutes, a total of 14.14 g. (0.23 mole) of ethylene glycol. The resulting solution was cloudy. Ethyl bromide (1.66 g.) was added and the mixture was heated unde... | CC1=CP(=O)(CCO)CC1 | null | null | null |
94,411 | ord_dataset-62e11cab5a6e47d89878616c244e20ef | null | 1982-01-01T00:05:00 | true | [Cl:1][C:2]1[C:3]([NH:12][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:16]([C:22]([F:25])([F:24])[F:23])=[C:15]([Cl:26])[C:14]=2[N+:27]([O-:29])=[O:28])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:30](Cl)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([N:12]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:10])[F:1... | O=[N+]([O-])c1cc(C(F)(F)F)c(Cl)c([N+](=O)[O-])c1Nc1ncc(C(F)(F)F)cc1Cl | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | In 20 ml. of pyridine, 2.3 g. of N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2,6-dinitro-3-chloro-4-trifluoromethylaniline (obtained in Preparation 4) was dissolved and a solution of 0.34 g. of acetylchloride in 10 ml. of pyridine was added dropwise to react them at 60° to 70° C. for 2 hours. Pyridine was distilled off fr... | CC(=O)N(c1ncc(C(F)(F)F)cc1Cl)c1c([N+](=O)[O-])cc(C(F)(F)F)c(Cl)c1[N+](=O)[O-] | null | null | null |
548,074 | ord_dataset-e967d076b4894c2c854795f019ed3c39 | null | 2002-01-01T00:06:00 | true | [CH:1]1([C:7](N(C2C=CC=CC=2OC(F)(F)F)CCN2CCN(C3C=CC([N+]([O-])=O)=CC=3OC)CC2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:40][C:41]([F:69])([F:68])[O:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][N:55]([CH2:58][C:59]2[CH:64]=[C:63]([O:65][CH3:66])[CH:62]=[CH:61][C:60]=... | COc1cc([N+](=O)[O-])ccc1N1CCN(CCN(C(=O)C2CCCCC2)c2ccccc2OC(F)(F)F)CC1 | COc1ccc(Br)c(CN2CCN(CCNc3ccccc3OC(F)(F)F)CC2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared following the procedure described for the compound of example 55, substituting the compound of example 74 for the compound of example 54. The residue was purified by flash chromatography (CHCl3-2 N methanolic NH3 100:1). Yield: 67%. | COc1ccc(Br)c(CN2CCN(CCN(C(=O)C3CCCCC3)c3ccccc3OC(F)(F)F)CC2)c1 | null | 67 | null |
1,745,708 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [O:1]=[C:2]1[C:7]2=[C:8]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10][N:6]2[N:5]=[C:4]([C@@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])[N:3]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.FC(F)(F)C(O)=O>>[NH2:20][C@H:18]([C:4]1[N:3]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:2](=[O:1])[C:7]2=[C:8... | C[C@H](NC(=O)OC(C)(C)C)c1nn2ccc(Sc3ccccc3)c2c(=O)n1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | (S)-tert-Butyl (1-(4-oxo-3-phenyl-5-(phenylthio)-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (190 mg, 0.41 mmol) was treated with trifluoroacetic acid (316 μl, 4.10 mmol) according to the method of Preparation 6 to obtain 142 mg (95% yield) of the title compound as a oil. Purity 95%. | C[C@H](N)c1nn2ccc(Sc3ccccc3)c2c(=O)n1-c1ccccc1 | null | 95.6 | null |
235,400 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [Si]([O:8][CH2:9][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]=[N:27][C:28]=2[NH2:32])[CH2:11][O:12][CH2:13][P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])(C(C)(C)C)(C)C>C(O)(=O)C>[CH2:17]([O:16][P:14]([CH2:13][O:12][CH2:11][CH:10]([O:22][N:23]1[CH:31]=[N:30][C:29]2[C:24]1=[N:25][CH:26]... | CCOP(=O)(COCC(CO[Si](C)(C)C(C)(C)C)On1cnc2c(N)ncnc21)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)adenine (170 mg, 0.35 mmol) in 80% aqueous acetic acid (5 ml) was stirred at 85° C. for 5 hours. After evaporation, the residue was chromatographed on silica eluting with ethyl acetate-methanol 5:1 affording 9-(1-diethoxyphosphorylmethoxy3... | CCOP(=O)(COCC(CO)On1cnc2c(N)ncnc21)OCC | null | null | null |
716,398 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [N:1]([C:4]([CH3:7])([CH3:6])[CH3:5])=[C:2]=[S:3].[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]=2)[CH2:14][CH2:13]1>>[C:4]([NH:1][C:2]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:19]=[C... | CC(C)C(=O)Nc1cccc(C2CCN(CCCN)CC2)c1 | CC(C)(C)N=C=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared by Procedure P and Scheme AB using 2-isothiocyanato-2-methylpropane and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide: ESMS m/e: 419.0 (M+H)+. | CC(C)C(=O)Nc1cccc(C2CCN(CCCNC(=S)NC(C)(C)C)CC2)c1 | null | null | null |
489,321 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.[NH:29]([CH2:33][CH2:34][OH:35])[CH2:30][CH2:31][OH:32].C(=O)([O-])O.[Na+]>C1COCC1>[OH:32][CH2:31][CH2:30][N:29](... | OCCNCCO | Cc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(CCl)cc2)CC3)cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | In THF (10ml) was dissolved N-[4-(chloromethyl)-phenyl]-7-(4-methylphenyl)-3,4-dihydronaphthalene-2-carboxamide (300mg), and to the mixture was added diethanolamine (222 μl). The mixture was refluxed for 34 hours. The reaction mixture was cooled to room temperature, and to the mixture was added 5% sodium hydrogen carbo... | Cc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(CN(CCO)CCO)cc2)CC3)cc1 | null | null | null |
1,356,754 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=2)[N:10]=[CH:9][C:8]=1[CH2:32][C:33]([NH2:35])=[O:34].Cl>CO.[OH-].[Na+].O>[F:39][C:37]1[CH:36]=[C:4]([CH:3]=[C:2]([F:1])[CH:38]=1)[CH2:5][... | Cc1ccc(S(=O)(=O)n2cc(-c3cc(NCc4cc(F)cc(F)c4)c(CC(N)=O)cn3)c3cccnc32)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 4 | 10 mg of 4-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide (the compound of Example 370) was dissolved in 0.5 mL of methanol, to which 0.5 mL of 6 mol/L sodium hydroxide in water was added, and stirred at room temperature for 4 hours. Under ice cooling, ... | NC(=O)Cc1cnc(-c2c[nH]c3ncccc23)cc1NCc1cc(F)cc(F)c1 | null | 40.4 | null |
471,588 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]([CH2:35]Cl)=[CH2:34]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:35][C:33]([Cl:32])=[CH2:... | C=C(Cl)CCl | CCCCOC(=O)c1ccc(N(CC)Cc2cc(Br)ccc2O)nn1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | Butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridazine-3-carboxy late (reference example 11) (0.28 g, 0.69 mmol) in DMF (4 ml) was treated with potassium carbonate (0.28 g, 2.05 mmol) followed by 2,3-dichloro-1-propene (168 mg, 140 μl, 1.4 mmol) and the mixture stirred at ambient temperature over the weekend. The... | C=C(Cl)COc1ccc(Br)cc1CN(CC)c1ccc(C(=O)OCCCC)nn1 | null | 72 | null |
713,153 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[C:5]([F:18])=[CH:4][N:3]=1.[OH:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[C:5]([F:18])=[CH:4][N:3]=[C:2]([NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[C:20]([OH:19])[CH:21]=3... | Nc1cccc(O)c1 | COc1ccc(Nc2nc(Cl)ncc2F)cc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-methoxyphenyl)-5-fluoro-4-pyrimidineamine and 3-hydroxyaniline were reacted to produce N4-(3-chloro-4-methoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NM... | COc1ccc(Nc2nc(Nc3cccc(O)c3)ncc2F)cc1Cl | null | null | null |
1,763,346 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH2:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1.FC(F)(F)S(O[CH2:36][CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]1[CH:51]=[CH:50][CH:49]=[... | COc1cn(CC(=O)OCc2ccccc2)c(=O)cc1-c1cc(Cl)ccc1C#N | CC(C)(C)[Si](OCCOS(=O)(=O)C(F)(F)F)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 1.00 g (2.45 mmol) of benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in the presence of 2.69 ml (2.69 mmol, 1.1 eq.) of bis(trimethylsilyl)lithium amide (1M in tetrahydrofuran) and 1.59 g (3.67 mmol, 1.5 eq.) of 2-{[tert-butyl(diphenyl)silyl]oxy}ethyl trifluoromethanesulphonate were reacted ... | COc1cn(C(CCO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C(=O)OCc2ccccc2)c(=O)cc1-c1cc(Cl)ccc1C#N | null | null | null |
1,508,612 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([O-:26])=[O:25]>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:33]([C:30]2[C... | CC(C)(C)OC(=O)NC1CCNCC1 | O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | Diisopropylethylamine (4.5 ml, 27.0 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (5.0 g, 20.0 mmol) in DCM (40 ml) at room temperature. To this mixture was added 4-nitrophenyl sulfonyl chloride (6.0 g, 27.0 mmol) in one portion and the mixture was stirred at room... | CC(C)(C)OC(=O)NC1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1 | null | 92.6 | null |
1,278,529 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[C:25]([Cu])#[N:26]>CN(C=O)C>[C:25]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]... | CC1(C)CCN(c2ccc(CNC(=O)OC(C)(C)C)cc2Br)CC1 | N#C[Cu] | 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 | 140 | null | In a screw cap pressure tube were tert-butyl 3-bromo-4-(4,4-dimethylpiperidin-1-yl)benzylcarbamate (105 mg, 0.26 mmol) and CuCN (47.3 mg, 0.53 mmol) suspended in DMF (1.0 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 140° C. overnight. The mixture was allowed to coo... | CC1(C)CCN(c2ccc(CNC(=O)OC(C)(C)C)cc2C#N)CC1 | null | 44.8 | null |
603,867 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].OS(O)(=O)=O.[BrH:16].CC(N=NC(C#N)(C)C)(C#N)C.OO>ClC1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([C:5]([Cl:8])=[CH:6][CH:7]=1)[CH2:9][Br:16] | Cc1c(Cl)ccc(Cl)c1C | Br | null | CC(C)(C#N)N=NC(C)(C)C#N | O=S(=O)(O)O | OO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 70 | 5 | 170.1 g (0.97 mol) of 3,6-dichloro-1,2-xylene are initially charged in 1180 ml of chlorobenzene, and 4.9 g of conc. H2SO4 and 203.1 g (1.18 mol) of 47% strength hydrobromic acid are added. The mixture is heated to 70° C., and 0.9 g of AIBN are added. Over a period of 5 h, 353.7 g (1.04 mol) of a 10% strength solution o... | Cc1c(Cl)ccc(Cl)c1CBr | null | null | null |
747,220 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | [C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][Si](C)(C)C)[CH:20]=4)[CH2:16][C:15](=[O:31])[NH:14][C:13]=3[CH:32]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].CO.C1COCC1>[C:25]([C:21]1[CH:20]=[C:19]([C:17]2[CH2:16][C:15](=[O:31])[NH:14][C:13]3[CH:32]=[... | C[Si](C)(C)C#Cc1cccc(C2=Nc3ccc(C#Cc4ccccc4)cc3NC(=O)C2)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | Prepared from 8-phenylethynyl-4-(3-trimethylsilanylethynyl-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 132) (63 mg, 0.146 mmol) by treatment with 1N NaOH (3 drops) in MeOH (3 mL) and THF (0.5 mL) at 23° C. for 2 h. Obtained as a brown solid (31 mg). | C#Cc1cccc(C2=Nc3ccc(C#Cc4ccccc4)cc3NC(=O)C2)c1 | null | 58.9 | null |
651,882 | ord_dataset-271c0b74f4794a06992957029b3151ba | null | 2004-01-01T00:10:00 | true | Br[C:2]1[CH:11]=[C:10]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:16][CH:17]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:30])[N:7]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[C:36](F)[CH:37]=1.C(O)(C(F)(F)F)=O>>[C:18]([N:15]1[CH2:14... | OB(O)c1cc(F)cc(F)c1 | CC(C)(C)N1CC=C(c2cc(Br)c3ccc(=O)n(-c4c(Cl)cccc4Cl)c3c2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 5-bromo-7-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(2,6-dichlorophenyl)quinolin-2(1H)-one (INTERMEDIATE ABA5) and using 3,5-difluorophenylboronic acid as described in EXAMPLE ABA11. 1H NMR (CD3OD, 500 MHz) TFA salt: δ 1.416 (s, 9H), 1.827 (m, 2H), 2.119 (d, J=14.7 Hz, 2H), 2.... | CC(C)(C)N1CCC(c2cc(-c3ccc(F)cc3)c3ccc(=O)n(-c4c(Cl)cccc4Cl)c3c2)CC1 | null | null | null |
495,334 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | [CH:1]([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH:29][C:30]3[N:35]=[C:34](Cl)[N:33]=[C:32]([Cl:37])[N:31]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH:44]([CH2:48][CH2... | OCCNCCO | COc1ccc(N=Nc2c(S(=O)(=O)OC(C)C)cc3cc(Nc4nc(Cl)nc(Cl)n4)ccc3c2O)cc1 | null | Cl | O=C([O-])[O-] | [Na+] | 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 | 60 | 7-(4,6-Dichloro-[1,3,5]-triazin-2-ylamino)-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 7, 200 mg, 0.36 mmol) in acetone (3 mL) was stirred under nitrogen with sodium carbonate (38 mg, 0.36 mmol). Diethanolamine (35 μL, 40 mg, 0.36 mmol) was added to the stirred suspension, and ... | COc1ccc(N=Nc2c(S(=O)(=O)OC(C)C)cc3cc(Nc4nc(Cl)nc(N(CCO)CCO)n4)ccc3c2O)cc1 | null | 77.8 | null |
1,655,624 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[F:14])=[N:4][N:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[F:14])=[N:4][N:5]([CH:8]([CH3:12])[C:9]([N:28]2[C... | Cc1c(Cl)c(C(F)(F)F)nn1C(C)C(=O)O | Fc1ccc(-n2ncc3c2CCCN3)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)propanoic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 2×1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g... | Cc1c(Cl)c(C(F)(F)F)nn1C(C)C(=O)N1CCCc2c1cnn2-c1ccc(F)cc1 | null | 75 | null |
1,742,335 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[H-].[Na+].F[C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:24]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:23])=[O:22])=[CH:17][CH:16]=1>O>[F:35][C:32]1[CH:31]=[CH:30][C:29]([N:24]([CH2:25][CH:26]([C... | CC(C)CN(c1ccc(F)cc1)S(=O)(=O)c1ccc(F)cc1 | CS(=O)(=O)N1CCC(O)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | To a solution of 1-methanesulfonyl-piperidin-4-ol (61 mg) in anhydrous tetrohydrofuran (5 mL) at room temperature was added NaH (60% dispersion in mineral oil, 15 mg, 369 μmol) and the reaction was stirred at room temperature for 30 minutes. 4-Fluoro-N-(4-fluoro-phenyl)-N-isobutyl-benzenesulfonamide (100 mg, 308 μmol) ... | CC(C)CN(c1ccc(F)cc1)S(=O)(=O)c1ccc(OC2CCN(S(C)(=O)=O)CC2)cc1 | null | 34.7 | null |
935,754 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][NH:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH2:19])=[NH:18])=[CH:12][CH:11]=1)=[O:4].CN(C)/[CH:22]=[CH:23]/[C:24]([C:26]1[N:30]([CH:31]([CH3:33])[CH3:32])[C:29]([CH3:34])=[N:28][CH:27]=1)=O>COCCO>[CH3:1][NH:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=... | Cc1ncc(C(=O)/C=C/N(C)C)n1C(C)C | CNC(=O)[C@H]1CCCN1c1ccc(NC(=N)N)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | 200 | null | (R)-1-(4-Guanidino-phenyl)-pyrrolidine-2-carboxylic acid methylamide (Method 59; 0.27 g, 1.0 mmol) and of (2E)-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one, (Method 24 of WO 03/076436; 0.15 g, 0.0.68 mmol) were added to 2-methoxyethanol (4 ml) and heated at 200° C. for 2 hours in the micro... | CNC(=O)[C@H]1CCCN1c1ccc(Nc2nccc(-c3cnc(C)n3C(C)C)n2)cc1 | null | 35 | null |
889,500 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3(O)[CH2:22][C@@H:21]([CH3:23])[O:20][C@@H:19]([CH3:24])[CH2:18]3)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C1CCN2C(=NCCC2)CC1>C(N(CC)CC)C>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH2:22][C@H:21]([C... | C[C@@H]1CC(O)(c2ccc3c(c2)CN(Cc2ccccc2)C3)C[C@H](C)O1 | null | null | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | null | Prepared in analogy to Example A65(a) from (2S,6R)-4-(2-benzyl-2,3-dihydro-1H-isoindol-5-yl)-2,6-dimethyl-tetrahydro-pyran-4-ol (Example A70(a)) and methanesulfonyl chloride, triethylamine, and DBU. Brown oil. MS (m/e): 320.3 ([M+H]+, 100%). | C[C@@H]1C=C(c2ccc3c(c2)CN(Cc2ccccc2)C3)C[C@H](C)O1 | null | null | null |
1,255,351 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [CH:1]([C:4]1[N:5]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]([C:13]#[N:14])=[C:4]2[CH:1]([CH3:3])[CH3:2])=[CH:... | COc1ccc(-n2c(C(C)C)c(C#N)c3ccccc32)cc1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 0 | null | 2-Isopropyl-1-(4-methoxy-phenyl)-1H-indole-3-carbonitrile (3 mg, 0.01 mmol) was dissolved in dry CH2Cl2 (0.5 ml) and stirred at 0° C. BBr3 (1M in CH2Cl2, 50 μl) was added and the mixture left in the fridge with stirring overnight. Some drops of MeOH were added and stirred. The solvent was removed in vacuo and the mixtu... | CC(C)c1c(C#N)c2ccccc2n1-c1ccc(O)cc1 | null | 39.8 | null |
910,077 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [NH2-].[Na+].[CH3:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6].[CH3:10][O:11][CH:12]([CH3:17])[C:13](OC)=[O:14].O>C(O)(=O)C>[CH3:10][O:11][CH:12]([C:13](=[O:14])[CH2:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[CH3:3])[CH3:17] | COC(=O)C(C)OC | CC(=O)C(C)(C)C | null | [NH2-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | O | null | null | null | null | null | null | null | null | null | null | 0.25 | In a 200 mL-volume flask equipped with a stirrer, a thermometer and a dropping funnel was placed 8.20 g (210 mmol) of sodium amide, and the flask was purged with argon. Then, 80 mL of toluene was placed in the flask. Subsequently, 15.1 g (150.8 mmol) of 3,3-dimethyl-2-butanone was slowly dropped into the flask, and the... | COC(C)C(=O)CC(=O)C(C)(C)C | null | 51.8 | null |
1,479,227 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | COC1C=CC(C[N:10]2[CH2:27][C:14]3([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11]2=[O:34])=CC=1.O.[ClH:36]>C(#N)C>[ClH:36].[C:28]1([CH:12]2[O:13][C:14]3([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH2:27][NH:10][C:11]2=[O:34])[CH:29]=[CH:30][CH:31... | COc1ccc(CN2CC3(CCN(C(=O)OC(C)(C)C)CC3)OC(c3ccccc3)C2=O)cc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | 2 | To tert-butyl 10-[(4-methoxyphenyl)methyl]-9-oxo-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate (215 mg, 0.46 mmol) in acetonitrile (2.5 mL) was added water (2.5 mL) followed by the addition of ceric ammonium nitrate (500 mg, 0.91 mmol). The reaction mixture was stirred for 2 hours. After this time, a furthe... | O=C1NCC2(CCNCC2)OC1c1ccccc1 | null | 100 | null |
602,761 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)[CH:7]=[CH:6]2.[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25].[Sn](Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:14][C... | COc1ccc2cc(-c3cc4ccccc4o3)ccc2c1 | CC(C)CC(=O)Cl | null | Cl[Sn](Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), was acylated with isovaleryl chloride (1.9 mL, 16 mmol), in presence of tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). Purification by flash chromatography using 15-100% chloroform in hexane ... | COc1ccc2cc(-c3oc4ccccc4c3C(=O)CC(C)C)ccc2c1 | null | null | null |
851,595 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH3:21]>O>[Cl:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([N+:8]([O-:11])=[O:9])=[CH:15][C:14]=1[CH3:21] | COc1ccc(C)c(Cl)c1 | O=[N+]([O-])O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | -5 | 1 | Acetic anhydride (10 mL) at −10° C. was treated with concentrated nitric acid (>69% pure, 1 mL) and then treated portionwise with 2-chloro-4-methoxy-1-methylbenzene (0.78 g, 5 mmol) at a rate that maintained the internal temperature lower than −5° C. The solution was stirred for additional one hour while warming to roo... | COc1cc(Cl)c(C)cc1[N+](=O)[O-] | null | 71 | null |
152,506 | ord_dataset-5944a40bb4504bbe8185cfdf2a811d03 | null | 1987-01-01T00:01:00 | true | C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([NH:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27])=[O:17])=O)C1C=CC=CC=1>CO.[C].[Pd]>[O:27]=[C:23]1[CH2:24][CH2:25][CH2:26][N:22]1[CH2:21][CH2:20][CH2:19][NH:18][C:16]([C@@H:12]1[CH2:13][CH2:14][CH2:15][NH:11]1)=[O:17] | O=C(NCCCN1CCCC1=O)[C@@H]1CCCN1C(=O)OCc1ccccc1 | null | null | [Pd] | 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 | In 150 ml of methanol was dissolved 4.32 g of compound (99) and the compound was hydrogenated using 432 mg of 10% palladium-carbon as a catalyst. Then, the catalyst was filtered off from the reaction mixture and the filtrate was concentrated to provide 1.99 g of (S)-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-2-pyrrolidinecarbo... | O=C(NCCCN1CCCC1=O)[C@@H]1CCCN1 | null | 71.9 | null |
501,791 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23](Cl)([O:25][CH2:26][CH:27]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24].Cl>O.O1CCOCC1.O1CCOCC1>[C:23]([NH:1][C:2]... | O=C(Cl)OCC1c2ccccc2-c2ccccc21 | Nc1cccc(-c2ccc(C(=O)O)cc2)c1 | null | Cl | O=C([O-])[O-] | [Na+] | 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 | 3 | 3 | Dissolve 3′-aminobiphenyl-4-carboxylic acid (Preparation B, Step 3) (1.07 g, 5 mmol) and Na2CO3 (1.33 g, 12.5 mmol ) in H2O-dioxane (2:1, 45 mL), and cool the solution to ˜3° C. Add Fmoc-Cl (1.3 g) in dioxane (10 ml); stir at ice bath temperature for 3 hours, allow to warm to room temperature and stir for another 4 hou... | O=C(Nc1cccc(-c2ccc(C(=O)O)cc2)c1)OCC1c2ccccc2-c2ccccc21 | null | null | null |
1,273,326 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([NH:14][CH3:15])[CH2:12][N:11]([C:16]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4([CH3:29])[CH2:28][CH2:27]4)=[O:25])[CH2:20][CH2:19]3)=[O:17])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:30]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35]([OH:37])=O)#[N:31]>>[C:30]([C:32... | CNC1CN(C(=O)C2CCN(C(=O)C3(C)CC3)CC2)CC1c1ccc(Cl)c(Cl)c1 | N#Cc1cc(C(=O)O)ccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described for the synthesis of example 97, the title compound 3-cyano-N-{(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-4-fluoro-N-methyl-benzamide was prepared from {4-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin... | CN(C(=O)c1ccc(F)c(C#N)c1)C1CN(C(=O)C2CCN(C(=O)C3(C)CC3)CC2)CC1c1ccc(Cl)c(Cl)c1 | null | null | null |
273,636 | ord_dataset-ee287d49cb8642e59ae9c3951f746312 | null | 1993-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([I:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:1][C:2]1[CH:3]=[C:4]([I:9])[CH:5]=[C:6]([O:8][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1 | BrCc1ccccc1 | Oc1cc(O)cc(I)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 | 3,5-Dihydroxyiodobenzene (Tex. J. Sci., 1977, 28, 253) was reacted with two equivalents of benzyl bromide using the procedure described in Example 1 to give 3,5-dibenzyloxyiodobenzene as an oil in 96% yield. This was reacted with n-butyl-lithium using the procedure described in Note c. immediately above except that the... | Ic1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 | null | 96 | null |
1,661,505 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | C([O:4][CH2:5][CH2:6][CH:7]([CH3:14])[CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)C.[OH-].[Na+]>O>[CH:9]1([CH2:8][CH:7]([CH3:14])[CH2:6][CH2:5][OH:4])[CH2:13][CH2:12][CH2:11][CH2:10]1 | CC(=O)OCCC(C)CC1CCCC1 | null | null | [Na+] | [OH-] | 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 | 92.5 | 11 | 4-cyclopentyl-3-methylbutyl acetate (1.98 kg, 10.0 mols, purity: 98%) sodium hydroxide (420 g, 10.5 mols) and water (8400 ml) were mixed together and heated at 90-95° C. under stirring for 10-12 h. The reaction mixture was cooled to 35° C. The aqueous phase was separated from the organic phase. The organic phase was wa... | CC(CCO)CC1CCCC1 | null | 91.5 | null |
704,839 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].[C:6]1([CH3:15])[C:7]([C:12](Cl)=[O:13])=[CH:8][CH:9]=[CH:10][CH:11]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:6]1([CH3:15])[C:7]([C:12]([NH:1][CH2:2][CH:3]([OH:5])[CH3:4])=[O:13])=[CH:8][CH:9]=[CH:10][CH:11]=1 | CC(O)CN | Cc1ccccc1C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | To 100 ml of a solution of 5.83 g of 1-amino-2-propanol in toluene, 18.0 ml of triethylamine was added, and 10 ml of a solution of 10.00 g of o-toluoyl chloride in toluene was added dropwise slowly with stirring under ice-cooling. After 30-minute-stirring, the ice-bath was removed, and the mixture was stirred for addit... | Cc1ccccc1C(=O)NCC(C)O | null | 58 | null |
1,627,363 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:15][C:16]1[N:21]=[C:20]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][C:31]([NH2:33])=[O:32])[C:19]([C:34]([F:37])([F:36])[F:35])=[CH:18][N:17]=1.C=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C... | CC(=O)O[BH-](OC(C)=O)OC(C)=O | COc1cc(C2CCNCC2)ccc1Nc1ncc(C(F)(F)F)c(CCc2ccccc2CC(N)=O)n1 | null | C=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 2 | 2-(2-(2-(2-((2-Methoxy-4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide (2) (2.249 g, 4.38 mmol) was dissolved in methanol (220 mL) and 37% formaldehyde solution (0.483 mL, 17.5 mmol) was added. After five minutes sodium tris(acetoxy)borohydride (4.641 g, 21.9 mmol) was added and... | COc1cc(C2CCN(C)CC2)ccc1Nc1ncc(C(F)(F)F)c(CCc2ccccc2CC(N)=O)n1 | null | 95 | null |
329,112 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[Br:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([NH2:19])=[C:14]([NH2:20])[CH:13]=1>>[Br:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][C:17]=1[F:18])[NH:19][C:1](=[O:8])[C:2](=[O:4])[NH:20]2 | CCOC(=O)C(=O)OCC | Nc1cc(F)c(Br)cc1N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 25 | null | The title compound was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (1.97 mL, 13.5 mmol) and 4-bromo-5-fluoro-1,2-diaminobenzene (277 mg, 1.35 mmol) was heated to reflux under N2 for 12 h. The reaction was allowed to cool to room ... | O=c1[nH]c2cc(F)c(Br)cc2[nH]c1=O | null | null | null |
1,548,215 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [NH2:1][C@H:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[C:6]([F:18])[CH:5]=1)[CH3:3].Cl[C:20]1[N:25]=[C:24]([N:26]2[C@@H:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][O:28][C:27]2=[O:34])[CH:23]=[CH:22][N:21]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[F:18][C:6]1[CH:5]=[C:4]([C@@H:2]([NH... | C[C@H](N)c1ccc(C(=O)N2CCCCC2)c(F)c1 | CC(C)[C@H]1COC(=O)N1c1ccnc(Cl)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 107.5 | null | To (S)-(4-(1-aminoethyl)-2-fluorophenyl)(piperidin-1-yl)methanone (0.019 g, 0.076 mmol) was added (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (0.028 g, 0.114 mmol), NMP (0.5 ml) and Hunig's Base (0.033 ml, 0.190 mmol). The reaction was heated at 105-110° C. for 16 hours or until done by LCMS. The reactio... | CC(C)[C@H]1COC(=O)N1c1ccnc(N[C@@H](C)c2ccc(C(=O)N3CCCCC3)c(F)c2)n1 | null | 11.6 | null |
1,400,243 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:44])[C@H:8]([NH:10][C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[C:30]5[C:25](=[CH:26][C:27]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:28][CH:29]=5)[N:24]([CH3:35])[N:23]=4)[N:20]=3)[N:15](COCC[Si](C)(C)C)[CH:14]=2)=[O:12])[CH3:9])[CH2:4]1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C... | C[C@@H](NC(=O)c1cn(COCC[Si](C)(C)C)c2ncc(-c3nn(C)c4cc(C(C)(C)C)ccc34)nc12)C(=O)N1CC(C#N)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 2-(6-tert-butyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide (129 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added TFA (0.75 mL). The reaction mixture was stirred at room temperature for 4 h ... | C[C@@H](NC(=O)c1c[nH]c2ncc(-c3nn(C)c4cc(C(C)(C)C)ccc34)nc12)C(=O)N1CC(C#N)C1 | null | 72.7 | null |
1,336,115 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[C:29]([O:31]C(C)C)=[O:30])=[O:8].[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37... | CC(C)OC(=O)c1c(C(=O)NCc2ccc(F)c(F)c2)c2ccc(OC(C)C)cc2n1Cc1ccccn1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of isopropyl 3-(3,4-difluorobenzylcarbamoyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate (Compound 101, 551 mg, 1.06 mmol) in MeOH (15 ml) and NaOH (1 M, 5.3 ml, 5.3 mmol) was stirred at room temperature for 4 h. The reaction was quenched cautiously with 6 M HCl at 0° C., extracted with EtOAc... | CC(C)Oc1ccc2c(C(=O)NCc3ccc(F)c(F)c3)c(C(=O)O)n(Cc3ccccn3)c2c1 | null | null | null |
1,492,127 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [OH:1][CH2:2][CH2:3][CH:4]([CH2:8][CH2:9][OH:10])[CH2:5][CH2:6][OH:7].[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1.Cl>ClCCl>[CH3:11][S:12]([O:1][CH2:2][CH2:3][CH:4]([CH2:8][CH2:9][O:10][S:12]([CH3:11])(=[O:14])=[O:13])[CH2:5][CH2:6][O:7][S:12]([CH3:11])(=[O:14])=[O:13])(=[O:14])=[O:13] | OCCC(CCO)CCO | CS(=O)(=O)Cl | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 24 | To an stirred ice-cooled solution of tris(2-hydroxyethyl)methane (10 g, 0.0676 mol) in dichloromethane (50 ml) was slowly dripped a solution of methanesulphonyl chloride (40 g, 0.349 mol) in dichloromethane (50 ml) under nitrogen at such a rate that the temperature did not rise above 15° C. Pyridine (21.4 g, 0.27 mol, ... | CS(=O)(=O)OCCC(CCOS(C)(=O)=O)CCOS(C)(=O)=O | null | null | null |
1,437,375 | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | null | 2014-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18](=[O:19])[C:17]3[C:12](=[C:13]([CH3:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]2[CH:21]([NH:23][CH3:24])[CH3:22])=[CH:5][CH:4]=1.[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>>[C:25]([C:29]1[CH:34]=[CH:33][C:... | CNC(C)c1nc2c(C)cccc2c(=O)n1-c1ccc(OC)cc1 | CC(C)(C)c1ccc(S(=O)(=O)Cl)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 | In a similar manner as described above, 3-(4-methoxyphenyl)-8-methyl-2-(1-methylaminoethyl)-3H-quinazolin-4-one, as prepared above in Example 5, was condensed with 4-tert-butylbenzenesulfonyl chloride to yield 4-tert-butyl-N-{1-[3-(4-methoxyphenyl)-8-methyl-4-oxo-3,4-dihydroquinazolin-2-yl]ethyl}-N-methylbenzenesulfona... | COc1ccc(-n2c(C(C)N(C)S(=O)(=O)c3ccc(C(C)(C)C)cc3)nc3c(C)cccc3c2=O)cc1 | null | null | null |
957,890 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][NH:7][C:6]1=[O:10].[H-].[Na+].Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:24]1([N:7]2[CH2:8][CH2:9][CH:5]([CH2:4][C:3]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:2]=3[Cl:1])[C:6]2=[O:10])[CH2:23][CH... | BrC1C=CCCC1 | O=C1NCCC1Cc1ccc(Cl)cc1Cl | null | O=C([O-])O | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | null | Charge a flask with 3-(2,4-dichloro-benzyl)-pyrrolidin-2-one (Preparation 19) (100 mg, 0.41 mmol), dissolve in THF (4 mL) and cool to 0° C. under nitrogen. Add NaH (15 mg, 0.61 mmol) and stir at 0° C. for 20 minutes. Add 3-bromo-cyclohexene (198 mg, 1.23 mmol) and stir at room temperature overnight. Pour into saturated... | O=C1C(Cc2ccc(Cl)cc2Cl)CCN1C1C=CCCC1 | null | 51.2 | null |
228,834 | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | null | 1991-01-01T00:06:00 | true | C([NH:9][C:10]([NH:22][CH2:23][CH2:24][CH2:25][C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)=[N:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)C1C=CC=CC=1>Cl>[NH:29]1[CH:30]=[C:26]([CH2:25][CH2:24][CH2:23][NH:22][C:10]([NH:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:2... | O=C(NC(=NCCCSc1ccccc1)NCCCc1c[nH]cn1)c1ccccc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.84 g (2 mmol) of N-benzoyl-N'-[3-(imidazol-4-yl) propyl]-N"-(3-phenylthiopropyl)-guanidine are heated under reflux in 18% hydrochloric acid for 7 hours and then worked up by a method analogous to that of Example 58. 0.71 g (91%) of a dry, hygroscopic foam is obtained. | N=C(NCCCSc1ccccc1)NCCCc1c[nH]cn1 | null | null | null |
684,402 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [ClH:1].[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)O)[CH2:9][CH2:8]1)=[O:6])[CH3:3].S(Cl)([Cl:25])=O>C1C=CC=CC=1>[ClH:25].[CH2:2]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH:14]([Cl:1])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=... | O=S(Cl)Cl | CCOC(=O)N1CCN(CC(O)c2ccc(F)cc2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 50 | null | To 8.3 g of 1-ethoxycarbonyl-4-[2-(4-fluorophenyl)-2-hydroxyethyl]piperazine hydrochloride were added 20 ml of benzene and 2.5 ml of thionyl chloride, followed by heating at 50° C. for 10 minutes. The reaction solution was concentrated under reduced pressure, 25% aqueous ammonia solution and water were poured, followed... | CCOC(=O)N1CCN(CC(Cl)c2ccc(F)cc2)CC1 | null | null | null |
173,168 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7](=[CH:23][N:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:25]=3)[C:8]([CH2:12][CH2:13][NH:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[N:9][C:10]=2[CH:11]=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][CH:34]=1>C(Cl)Cl>[Cl:32][C... | O=C=Nc1ccc(Cl)cc1 | N#Cc1ccc(NCCc2nc3cc(Cl)ccc3c3nn(-c4ccccc4)cc23)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 150 mg (0.35 mmol) of the compound of Example 1, 100 mg (0.65 mmol) of p-chlorophenylisocyanate, and 10 ml of methylene chloride is stirred at ambient temperature overnight. The resulting precipitate is collected to furnish 121 mg (60%) of title compound: IR (KBr) 3360, 2220, 1660, 1590, 1520, 1500, 1490 c... | N#Cc1ccc(N(CCc2nc3cc(Cl)ccc3c3nn(-c4ccccc4)cc23)C(=O)Nc2ccc(Cl)cc2)cc1 | null | 59.9 | null |
78,318 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C@@H:8]12[C:17](=O)[O:16][C:14](=[O:15])[C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2.CS(O)(=O)=O>C1(C)C(C)=CC=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:14](=[O:15])[CH:9]3[CH:8]([CH2:13][CH2:12][CH2:11][CH2:10]3)[C:17]2=[O:16])=[CH:3][CH:4]=1 | Nc1ccncc1 | O=C1OC(=O)[C@@H]2CCCC[C@H]12 | null | CS(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | 18 | The starting material is prepared as follows: The mixture of 23.5 g of 4- aminopyridine, 38.5 g of cis-1,2-cyclohexanedicarboxylic acid anhydride and 400 ml of xylene is refluxed for 42 hours while stirring and separating the water formed. After the first half-hour, and after 18 hours, 1 ml of methane sulfonic acid is ... | O=C1C2CCCCC2C(=O)N1c1ccncc1 | null | null | null |
232,573 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | C[CH:2]([CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O)[C:3](C)(C)[C:4](C)([P:10]([OH:13])([OH:12])=[O:11])[O:5]P(O)(O)=O>Cl>[NH2:18][CH2:17][CH2:2][CH2:3][C:4]([P:10](=[O:11])([OH:12])[OH:13])([P:10](=[O:11])([OH:13])[OH:12])[OH:5] | CC(CN1C(=O)c2ccccc2C1=O)C(C)(C)C(C)(OP(=O)(O)O)P(=O)(O)O | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Tetramethyl-1,1-bisphosphono-1-hydroxy-4-phthalimidobutane 40 g (0.091 mole) from Step 4 was dissolved in 200 ml of 6N HCl and the solution refluxed for 18 hours. | NCCCC(O)(P(=O)(O)O)P(=O)(O)O | null | null | null |
671,983 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | F[C:2]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:17][NH2:18]>N1C=CC=CC=1>[F:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[NH:18][N:17]=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1 | NN | O=C(c1ccccc1)c1cc(F)ccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2,5-difluorobenzophenone (0.655 g, 3.0 mmol) and hydrazine (1.0 mL) in dried pyridine (10 mL) was heated at 130° C. for 5 hours and then concentrated and purified by chromatography (SiO2, 15-30% ethyl acetate/hexane) to provide the title compound (0.254 g, 40% yield): mp 124-125° C.; 1H NMR (CDCl3) δ 10.8... | Fc1ccc2[nH]nc(-c3ccccc3)c2c1 | null | 40 | null |
690,535 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[S:24][C:23]3[C:18](=[N:19][CH:20]=[CH:21][C:22]=3[Cl:25])[CH:17]=2)=[O:15])[CH2:10]1>>[Cl:25][C:22]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:17]=[C:16]([C:14]([N:11]3[CH2:12][CH2:13][CH:9]([NH:8][S:3](=[O:5])(=[O:4])[N:2]([CH3:7])[... | NC1CCN(C(=O)c2cc3nccc(Cl)c3s2)C1 | CN(C)S(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from dimethylsulfamoyl chloride and (3-amino-pyrrolidin-1-yl)-(7-chloro-thieno[3,2-b]pyridin-2yl)-methanone by a procedure analogous to Example 64C. MS: 389/391 (MH+); HPLC Rf: 4.26 min.; HPLC purity 99%. | CN(C)S(=O)(=O)NC1CCN(C(=O)c2cc3nccc(Cl)c3s2)C1 | null | null | null |
93,585 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | Cl.[F:2][C:3]1[C:8]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([F:17])[C:6]([F:18])=[C:5]([F:19])[C:4]=1[F:20].[Cl:21]C1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[F:17][C:7]1[C:8]([S:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:26])=[C:3]([F:2])[C:4]([F:20])=[C:5]([F:19])[C:6]=1[F:18].[ClH:... | O=C(OO)c1cccc(Cl)c1 | Fc1c(F)c(F)c(SCc2ccccn2)c(F)c1F | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A stirred suspension of 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated portionwise with m-chloroperoxybenzoic acid (1.41 g) over 1/2 hour. The mixture was allowed to warm to ambient temperature, sufficient methylene chloride was added to form a solu... | O=S(Cc1ccccn1)c1c(F)c(F)c(F)c(F)c1F | null | null | null |
11,364 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]1[N:9]=[C:8](S(C)=O)[N:7]=[C:6]([N:13]2[CH2:18][CH2:17][S:16](=[O:19])[CH2:15][CH2:14]2)[C:5]=1[N+:20]([O-:22])=[O:21])[CH3:2].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.O>C(O)C>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[N:7]=[C:6]([N:13]2[CH2:18][CH2:17][S:1... | CCOc1nc(S(C)=O)nc(N2CCS(=O)CC2)c1[N+](=O)[O-] | C1CNCCN1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | 1 gm (2.9 mols) of 6-ethoxy-2-methylsulfinyl-5-nitro-4-(1-oxido-thiomorpholino)-pyrimidine [m.p. 164°-165°C, prepared from 6 ethoxy-2-methylthio-5-nitro-4-(1-oxido-thiomorpholino)-pyrimidine and 30% hydrogen peroxide in dilute acetic acid] was refluxed together with 5 gm (58 millimols) of piperazine in 50 ml of ethanol... | CCOc1nc(N2CCNCC2)nc(N2CCS(=O)CC2)c1[N+](=O)[O-] | null | null | null |
847,169 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | C(Cl)Cl.[N+:4]([O-:7])([OH:6])=[O:5].OS(O)(=O)=O.O[CH2:14][CH2:15][CH2:16][C:17]([O-:19])=[O:18].[K+]>O>[N+:4]([O:7][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])([O-:6])=[O:5] | O=[N+]([O-])O | O=C([O-])CCCO | null | O=S(=O)(O)O | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O | null | null | null | null | null | null | null | null | null | null | 0.25 | CH2Cl2 (10 ml) was added to the HNO3/H2SO4 mixture, and the resulting solution was stirred for 15 minutes. Potassium 4-(hydroxy)butanoate (500 mg, 3.52 mmol) was then added in small portions to the methylenechloride solution kept at 0-5° C. The mixture was kept under stirring for 6 hours while the temperature was allow... | O=C(O)CCCO[N+](=O)[O-] | null | null | null |
531,326 | ord_dataset-7774db17e619477ea20ee621abe71257 | null | 2002-01-01T00:01:00 | true | [OH:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]#[N:29])[CH:23]=3)[C:12]3[C:17]([CH:18]=2)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][CH:13]=3)=[O:9])=[CH:4][CH:3]=1.[ClH:32].[NH3:33]>>[ClH:32].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11... | N | COc1cccc2c1cc(C(=O)NCc1ccc(O)cc1)n2Cc1cccc(C#N)c1 | 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 | This compound was prepared from 1-(3-cyano-benzyl)-4-methoxy-1H-indole-2-carboxylic acid 4-hydroxy-benzyl amide (200 mg, 0.49 mmol), hydrogen chloride, and liquid ammonia analogously to example 19/3. Purification by reversed phase chromatography on RP18 material with water/ethanol/acetic acid 7:3:0.1 and lyophilization... | COc1cccc2c1cc(C(=O)NCc1ccc(O)cc1)n2Cc1cccc(C(=N)N)c1 | null | 79 | null |
1,593,565 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][C:6]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:7]=1[C:8]#[N:9].Cl[C:21]1[CH:22]=[C:23]2[N:30]([CH:31]3[CH2:33][CH2:32]3)[CH2:29][CH2:28][N:24]2[C:25](=[O:27])[N:26]=1>>[CH:31]1([N:30]2[C:23]3[N:24]([C:25](=[O:27])[N:26]=[C:21]([O:15][CH2:14][C:11]4[CH:1... | N#Cc1cc(CO)ccc1Oc1ccc(F)c(F)c1 | O=c1nc(Cl)cc2n1CCN2C1CC1 | null | null | null | null | null | null | null | 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 similar to that described for E9 starting from 2-(3,4-difluorophenoxy)-5-(hydroxymethyl)benzonitrile and 7-chloro-1-cyclopropyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one. | N#Cc1cc(COc2cc3n(c(=O)n2)CCN3C2CC2)ccc1Oc1ccc(F)c(F)c1 | null | null | null |
906,800 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:35]1([CH2:40][CH2:41][C:42](Cl)=[O:43])[CH2:39][CH2:38][CH2:3... | O=C(Cl)CCC1CCCC1 | CCCCc1ccc(C#Cc2ccc(CNCc3ccc4c(c3)C(=O)OC(C)(C)O4)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The titled compound was prepared following the procedure B using 6-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-2,2-dimethyl-4H-1,3-benzodioxin-4-one and 3-cyclopentylpropanoyl chloride as a colorless oil (72%). 1H NMR (CDCl3, 300 MHz) δ 7.74 (m, 1H), 7.50 (m, 2H), 7.43 (m, 2H), 7.35-7.21 (m, 1H), 7.20-6.85 (m, 5H... | CCCCc1ccc(C#Cc2ccc(CN(Cc3ccc4c(c3)C(=O)OC(C)(C)O4)C(=O)CCC3CCCC3)cc2)cc1 | null | null | null |
1,157,066 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH2:1]([N:8]1[C:12]([CH2:13][CH:14]([C:19](=O)[CH2:20][CH3:21])[C:15](=O)[CH2:16][CH3:17])=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH:25][NH2:26])[CH3:24]>>[CH2:1]([N:8]1[C:12]([CH2:13][C:14]2[C:19]([CH2:20][CH3:21])=[N:26][N:25]([CH2:23][CH3:24])[C:15]=2[CH2:16][CH3:17])=[CH:11][N:10]... | CCC(=O)C(Cc1cncn1Cc1ccccc1)C(=O)CC | CCNN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-(3-Benzyl-3H-imidazol-4-ylmethyl)-1,3,5-triethyl-1H-pyrazole was prepared from 4-(3-benzyl-3H-imidazol-4-ylmethyl)-heptane-3,5-dione and ethylhydrazine in analogy to Example 55 b): off-white solid; MS (ISP): 323.3 ((M+H)+.). | CCc1nn(CC)c(CC)c1Cc1cncn1Cc1ccccc1 | null | null | null |
1,017,369 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)[NH:8][CH2:7][CH2:6][C:5]2=1.CCN(CC)CC.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C1COCC1>[C:29]([N:8]1[CH2:7][CH2:6][C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=3)[NH:11][C:10]=2[CH:9]1[C:15]... | CC(=O)OC(C)=O | Cc1ccc2[nH]c3c(c2c1)CCNC3c1cccc(O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of 6-methyl-1-(3-hydroxyphenyl)-1,2,3,4-tetrahydro-beta-carboline (1 equiv) in THF was added Et3N (2.2 equiv) and acetic anhydride (1.2 equiv). After one hour, the solution was purified by prep-HPLC to give 3-(2-acetyl-6-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)phenol 1. | CC(=O)N1CCc2c([nH]c3ccc(C)cc23)C1c1cccc(O)c1 | null | null | null |
227,500 | ord_dataset-d98d003e9abb4b579746c5a361466e14 | null | 1991-01-01T00:05:00 | true | [F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[N:19]3[C:20]4[N:12]([C:13](=[O:22])[NH:14][C:15](=[O:21])[C:16]=4[CH:17]=[N:18]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH2:28][CH3:29]>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:28]([N:14]1[C:13](=[O:22])[N:12]2[C:20]3[N:19]([C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([... | O=c1[nH]c(=O)n2c3c1cnn3C(c1cccc(C(F)(F)F)c1)=CC2 | CCI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a stirred mixture of 5.0 g of 8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione (prepared as described in Example 14) in 50 ml of dry N,N-dimethylformamide, under nitrogen, is added 800 mg of 60 percent sodium hydride (dispersion in mineral oil). The mixture is stirred at room temper... | CCn1c(=O)c2cnn3c2n(c1=O)CC=C3c1cccc(C(F)(F)F)c1 | null | null | null |
1,216,189 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C1(OC(=O)[N:9]([C:19]2[CH:24]=[C:23]([O:25][C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]4([C:38](=[O:47])[NH:39][C:40]5[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=5)[CH2:37][CH2:36]4)=[O:34])=[CH:28][C:27]=3[F:48])[CH:22]=[CH:21][N:20]=2)[C:10](OC2C=CC=CC=2)=[O:11])C=CC=CC=1.[CH3:50][N:51]1[CH2:56][CH2:55][N:54]([... | O=C(Oc1ccccc1)N(C(=O)Oc1ccccc1)c1cc(Oc2ccc(NC(=O)C3(C(=O)Nc4ccc(F)cc4)CC3)cc2F)ccn1 | CN1CCN(C2CCNCC2)CC1 | 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 solution of [4-(2-fluoro-4-{[1-(4-fluorophenylcarbamoyl)cyclopropanecarbonyl]amino}phenoxy)pyridin-2-yl]-N-(phenoxycarbonyl)carbamic acid phenyl ester (66 mg) in N,N-dimethylformamide (1.0 ml) was added 1-methyl-4-(piperidin-4-yl)piperazine (73.3 mg) at room temperature, followed by stirring overnight. The reactio... | CN1CCN(C2CCN(C(=O)Nc3cc(Oc4ccc(NC(=O)C5(C(=O)Nc6ccc(F)cc6)CC5)cc4F)ccn3)CC2)CC1 | null | 95.5 | null |
105,152 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | C1[O:14][C:4]([CH3:13])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)OC1.[OH-].[Na+].Br[CH2:18][CH2:19][CH2:20][OH:21]>O>[OH:21][CH2:20][CH2:19][CH2:18][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:14])[CH3:13])=[CH:11][CH:10]=1 | CC1(Cc2ccc(O)cc2)OCCO1 | OCCCBr | null | [Na+] | [OH-] | 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 | 0.5 | 1-(4-Hydroxyphenyl)propan-2-one ethylene ketal (3.88 g) was added to a solution of sodium hydroxide (1.5 g) in water (30 ml) and the mixture was stirred at room temperature for 30 minutes. 1-Bromo-3-hydroxypropane (2.98 g) was added and the mixture was boiled under reflux with stirring for 11/2 hours. After cooling wat... | CC(=O)Cc1ccc(OCCCO)cc1 | null | 94.7 | null |
584,661 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1 | COC(=O)c1ccc(-c2cccc(OC)c2)cc1 | null | null | BrB(Br)Br | 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 | 25 | 4 | A solution of boron tribromide in dichloromethane (1N, 24.8 ml) was added to a solution of methyl 3′-methoxybiphenyl-4-carboxylate (2.00 g) in anhydrous dichloromethane (10 ml) at −70° C. The mixture was stirred at ambient temperature for 4 hours and a mixture of ice and water was added to the reaction mixture in an ic... | O=C(O)c1ccc(-c2cccc(O)c2)cc1 | null | 102.9 | null |
1,323,883 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]12([CH:9]3[CH2:10][CH2:11][CH:6]1[C:7](=[O:12])[CH2:8]3)[CH2:5][CH2:4][CH2:3][CH2:2]2.C(O)(=[O:15])C>>[C:1]12([CH:6]3[CH2:11][CH2:10][CH:9]1[C:8](=[O:15])[C:7]3=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5]2 | O=C1CC2CCC1C21CCCC1 | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 120 | null | As described in Example 1 Step B]: from spiro[bicyclo[2.2.1]heptane-7,1′-cyclopentan]-2-one, 1.05 g, SeO2 (1.56 g) in acetic acid (5 ml) on heating at 120° C. for 12 h, purification crude product by flash chromatography (heptane/AcOEt 100-90%, there was obtained spiro[bicyclo[2.2.1]heptane-7,1′-cyclopentane]-2,3-dione ... | O=C1C(=O)C2CCC1C21CCCC1 | null | null | null |
1,116,702 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [CH:1](=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:7]([O:11][C:12]([NH:14][CH:15](P(OC)(OC)=O)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12]([NH:14]/[C:15](=[CH:1]\[C:2]([CH3:5])([CH3:4])[CH3:3])/[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8] | CC(C)(C)C=O | COC(=O)C(NC(=O)OC(C)(C)C)P(=O)(OC)OC | 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 | -70 | 96 | Pivalaldehyde (303.2 g, 3.41 mol, 10 eq.) and methyl {[(tert-butoxy)carbonyl]amino}-(dimethoxyphosphoryl)acetate (101.5 g, 0.341 mol, 1.0 eq.) are dissolved in THF (800 ml) and cooled to −70° C. At −70° C., TMG (78.7 g, 0.683 mmol, 6.95 ml, 2.0 eq.) is slowly added dropwise and the mixture is then stirred at −70° C. fo... | COC(=O)/C(=C/C(C)(C)C)NC(=O)OC(C)(C)C | null | null | null |
604,695 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([O:18][C:19]([O:21]C2C=CC=CC=2)=O)[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:33].C(O)(=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:33][C:19](=[O:21])[O:18][C:9]=2[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[... | [NH4+] | CCOC(=O)CCCC(OC(=O)Oc1ccccc1)C(=O)c1ccc(F)cc1 | null | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 6-(4-fluorophenyl)-6-oxo-5-phenoxycarbonyloxyhexanoate (18.0 g), ammonium acetate (17.8 g) and acetic acid (100 ml) was stirred with heating under reflux for 2 hours. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate (200 ml×2), and the extract was washed with water... | CCOC(=O)CCCc1oc(=O)[nH]c1-c1ccc(F)cc1 | null | null | null |
712,020 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [Cl:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([Cl:9])[C:6](=[O:8])[CH:7]=1.OS(O)(=O)=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([Cl:9])[C:6](=[O:8])[C:7]=1[C:21]1[C:20]2[C:24](=[CH:25][CH:2... | O=C1C=C(Cl)C(=O)C=C1Cl | COc1ccc2[nH]ccc2c1 | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | O=S(=O)(O)O | null | 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 | null | 2 | To a solution of 2,5-dichloro-1,4-benzoquinone (0.242 g, 1.37 mmol) in THF (3 mL) was added H2SO4 (35 μL, 0.68 mmol) at room temperature. To this mixture was added 5-methoxyindole (0.100 g, 0.68 mmol). After the reaction mixture was stirred for 1 hour at room temperature under nitrogen protection, DDQ (0.232 g, 1.02 mm... | COc1ccc2[nH]cc(C3=C(Cl)C(=O)C=C(Cl)C3=O)c2c1 | null | 96.3 | null |
1,286,146 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH:22]=O)[CH:6]=1.[CH3:25][NH2:26]>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14... | COC(=O)Cc1cccc(Oc2ccc(C(F)(F)F)cc2C=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 | null | null | Prepared according to the procedure described in Example 3, Step 2, using the following starting materials: [3-(2-formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester and methylamine (2M in THF). | CNCc1cc(C(F)(F)F)ccc1Oc1cccc(CC(=O)OC)c1 | null | null | null |
144,953 | ord_dataset-d6cdba90760a47779a36ece5962905eb | null | 1986-01-01T00:06:00 | true | [C:1]1([C:7]2[O:8][CH2:9][CH:10]([CH2:12][S:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:29])C=1>C(Cl)Cl>[C:1]1([C:7]2[O:8][CH2:9][CH:10]([CH2:12][S:13]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)=[O:29])[N:11]=2)[CH:2]=[CH:3][CH... | Oc1ccc(SCC2COC(c3ccccc3)=N2)cc1 | O=C(OO)c1cccc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 2.85 q (10.0 mm) of the sulfide prepared in Example 1 in 50 ml methylenechloride at 25° C. was added 2.1 g (12 mm) of 90% MCPBA. Small portions of MCPBA were added until conversion was completed as indicated by thin layer chromatography. The soution was poured into 50 ml methylenechloride, washed with ... | O=S(CC1COC(c2ccccc2)=N1)c1ccc(O)cc1 | null | null | null |
1,713,758 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[N:14]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:13]2[C:8](=[N:9][C:10]([N:24](C(OC(C)(C)C)=O)[NH:25][C:26](OC(C)(C)C)=O)=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].[CH3:40]C(O)=O>>[CH3:40][C:26]1[N:9]2[C:8]3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:14]([S:1... | CCOC(=O)c1cc2nc(N(NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ccc2n1S(=O)(=O)c1ccccc1 | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 180 | null | A solution of di-tert-butyl 1-[2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (2.5 g, 4.4 mmol, from Step 2) in AcOH (40 mL) was split into 5 batches and each was heated in the microwave to a temperature of 180° C. for 3 minutes. The reaction contents were pooled and AcO... | CCOC(=O)c1cc2c(ccc3nnc(C)n32)n1S(=O)(=O)c1ccccc1 | null | 74 | null |
724,677 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[ClH:24]>O1CCOCC1>[ClH:24].[NH:15]1[CH2:16][CH:13]([CH2:12][S:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:14]1 | CC(C)(C)OC(=O)N1CC(CS(=O)(=O)c2ccc(C#N)cc2)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 0.17 | The foregoing tert-butyl 3-{[(4-cyanophenyl)sulfonyl]methyl}azetidine-1-carboxylate (200 mg, 0.59 mmol) was treated with 4N HCl in 1,4-dioxane and stirred for 10 minutes. The reaction was evaporated without heat to give the title compound crude as a white solid (100 mg). 1H NMR (500 MHz, CDCl3) δ 2.99–3.05 (1H, m), 3.7... | N#Cc1ccc(S(=O)(=O)CC2CNC2)cc1 | null | null | null |
269,694 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | [C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[NH2:12][C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[N:16]=[C:15]([CH2:21][CH3:22])[C:14]=1[C:23](OC)=[O:24].[Na]>C(O)C>[CH2:21]([C:15]1[N:16]=[C:17]([CH2:19][CH3:20])[CH:18]=[C:13]2[C:14]=1[C:23]([OH:24])=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:3](=[O:5])[NH:1... | CCOC(=O)CC(=O)OCC | CCc1cc(N)c(C(=O)OC)c(CC)n1 | null | [Na] | 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 | 150 | null | Diethyl malonate (14.5 ml) and methyl 4-amino-2,6-diethylpyridine-3-carboxylate (21.3 g) was added to a solution of sodium (2.33 g) in ethanol (60 ml) and the resulting mixture was heated at 150° C. for 20 hours in an autoclave. The mixture was allowed to cool and then volatile material was removed by evaporation and t... | CCOC(=O)c1c(O)c2c(CC)nc(CC)cc2[nH]c1=O | null | null | null |
431,986 | ord_dataset-8cbb58558c904b2b85fa7a1b084a0de9 | null | 1999-01-01T00:06:00 | true | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].[O:6]=[C:7]1[C:16](=[O:17])[NH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=2)[NH:8]1.C(O)(=O)C>O>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:18]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:6])[C:16](=[O:17])[NH:15]2)(=[O:19])=[O:20] | COCCN | O=c1[nH]c2ccc(S(=O)(=O)Cl)cc2[nH]c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 48 | To a solution of 7.51 g (0.1 mole) of 2-methoxyethylamine in 20 ml of water 5.21 g (0.02 mole) of 1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxalinesulfonyl chloride are added in small portions, under stirring, and the mixture is stirred at room temperature for 16 hours. It is allowed to stand further for 2 days, and then 15 m... | COCCNS(=O)(=O)c1ccc2[nH]c(=O)c(=O)[nH]c2c1 | null | 63 | null |
755,752 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:18][CH2:19][O:20]S(C1C=CC(C)=CC=1)(=O)=O.C([O:33][C:34](=[O:54])[C:35]([CH3:53])([O:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:36][C:37]1[CH:42]=[CH:41][C:40](O)=[C:39]([O:44][CH3:45])... | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccc(-c4cccs4)cc3)oc2C)cc1 | CCOC(=O)C(C)(Cc1ccc(O)c(OC)c1)Oc1ccccc1 | 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 | 55 | null | Toluene-4-sulfonic acid 2-(5-methyl-2-(4-thiophen-2-yl-phenyl)-oxazol-4-yl)ethyl ester (0.132 mmol) (see Ex. 3, Part B) was added to a one dram, screw-cap vial and diluted with ethanol (0.5 mL). To this solution are added 3-(4-hydroxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic acid ethyl ester(see Ex. 7, Part D) (0.5... | COc1cc(CC(C)(Oc2ccccc2)C(=O)O)ccc1OCCc1nc(-c2ccc(-c3cccs3)cc2)oc1C | null | null | null |
881,625 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | [Li]C.C[Si](C)(C)[O:5][C:6]([CH3:8])=[CH2:7].[CH2:11]([Si:14]1(Cl)[O:18][C@@H:17]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:16]([C:24]([CH3:28])([O:26][CH3:27])[CH3:25])[O:15]1)[CH:12]=[CH2:13]>CCCCC>[CH2:11]([Si:14]1([O:5][C:6]([CH3:8])=[CH2:7])[O:18][C@@H:17]([C:19]([O:22][CH3:23])([CH3:21])[CH3:20])[C@H:16]([C:2... | C=C(C)O[Si](C)(C)C | C=CC[Si]1(Cl)O[C@@H](C(C)(C)OC)[C@H](C(C)(C)OC)O1 | null | [Li]C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCC | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | To a cooled (0° C.) solution of MeLi (13.0 mL; 21 mmol; 1.6 M in Et2O) was added 2-(trimethylsilyloxy)propene (2.8 g; 21 mmol). The solution was stirred 30 minutes at 0° C., and then warmed to room temperature and was stirred for 1 hour. The mixture was recooled to 0° C., and (4R,5R)-2-allyl-2-chloro-4,5-bis-(1-methoxy... | C=CC[Si]1(OC(=C)C)O[C@@H](C(C)(C)OC)[C@H](C(C)(C)OC)O1 | null | 43.2 | null |
189,782 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([OH:22])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:26])=O>C1C=CC=CC=1>[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([Cl:26])=[O:22... | O=C(O)CN1C(=O)O[C@H](c2ccccc2)[C@@H]1c1ccccc1 | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A suspension composed of (4,5-cis-diphenyl-2-oxo-3-oxazolidinyl)acetic acid (29.1 g, 97.9 mmol), oxalyl chloride (18.6 g, 147 mmol) and benzene (120 ml) was refluxed for 2 hours. When the suspension became homogeneous, the solvent was distilled off. By the above procedure there was obtained the title compound (30.9 g) ... | O=C(Cl)CN1C(=O)O[C@H](c2ccccc2)[C@@H]1c1ccccc1 | null | 100 | null |
381,829 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH2:11][N:10]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)(=[O:16])=[O:15])[N:9]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([N:10]2[CH2:11][CH2:12][CH2:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]... | O=[N+]([O-])c1ccc(S(=O)(=O)N2CCCC(c3ccc(Cl)cc3)=N2)cc1 | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 80 | null | (4-Chlorophenyl)-1-(4-nitrobenzenesulfonyl)-1,4,5,6-tetrahydropyridazine (2.12 g, 5.60 mmol) was suspended in acetic acid at 80° C. Iron filings (3.0 g) were added to this suspension and the resulting reaction mixture was heated at 80° C. for 30 minutes and filtered. Upon cooling the title compound precipitated out of ... | Nc1ccc(S(=O)(=O)N2CCCC(c3ccc(Cl)cc3)=N2)cc1 | null | null | null |
556,949 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][NH2:8])=[CH:4][C:3]=2[O:2]1.Cl[C:14]1[C:15]2[C:28]([CH3:29])=[CH:27][S:26][C:16]=2[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:19]=1>>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]1[N:19]=[C:14]([NH:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:11]... | Cc1csc2nc(-c3ccccn3)nc(Cl)c12 | NCCc1ccc2c(c1)OCO2 | null | null | null | null | null | null | null | 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 3,4-methylenedioxyphenethylamine with 4-chloro-2-(pyridin-2-yl)-5-methyl-thieno-[2,3-d]-pyrimidine yields 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methyl-thieno-[2,3-d]-pyrimidine. | Cc1csc2nc(-c3ccccn3)nc(NCCc3ccc4c(c3)OCO4)c12 | null | null | null |
1,164,127 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]1=[O:20])[CH3:2].O.NN>CO.[Ni]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:7]([CH2:6][CH2:5][CH2:4][N:3]([CH2:21][CH3:22])[CH2:1][CH3:2])[C:8](=[O:20])[CH2:9][CH2:10]... | CCN(CC)CCCN1C(=O)CCc2cc([N+](=O)[O-])ccc21 | null | null | [Ni] | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | null | 1-(3- (Diethylamino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (93 mg, 0.305 mmol) in dry methanol (5 mL) was treated with Ra—Ni (slurry in water, ˜0.05 g) followed by hydrazine hydrate (95 uL, 3.05 mmol) at room temperature and the resulting mixture was refluxed for 30 minutes. The reaction was cooled to room tempe... | CCN(CC)CCCN1C(=O)CCc2cc(N)ccc21 | null | null | null |
914,058 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [F:1][C:2]1([F:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([N:21]2[CH2:25][CH2:24][CH:23]([N:26]([CH3:28])[CH3:27])[CH2:22]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)#[N:31].N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[... | N#Cc1cccc(B(O)O)c1 | CN(C)C1CCN(C(=O)c2ccc3[nH]c(C(=O)N4CCC(F)(F)CC4)cc3c2)C1 | null | [Cu+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was synthesized in analogy to example 66, from (RS)-(4,4-difluoro-piperidin-1-yl)-[5-(3-dimethylamino-pyrrolidine-1-carbonyl)-1H-indol-2-yl]-methanone (example 42, intermediate a)), 3-cyanophenylboronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a colorle... | CN(C)C1CCN(C(=O)c2ccc3c(c2)cc(C(=O)N2CCC(F)(F)CC2)n3-c2cccc(C#N)c2)C1 | null | 40 | null |
1,239,907 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]=1[S:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>>[CH2:20]([O:19][C:17]1[CH:16]=[CH:15][C:14]([S:27][C:28]2[CH:29]=[CH:30][... | Nc1cc(OCc2ccccc2)ccc1Sc1ccc(O)cc1 | Clc1ccnc2ncccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product from Example 16c (100 mg, 0.559 mmol) was reacted with 4-(2-amino-4-benzyloxy-phenylsulfanyl)-phenol (224 mg, 0.559 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (mg, %). 1H NMR (300 ... | Oc1ccc(Sc2ccc(OCc3ccccc3)cc2Nc2ccnc3ncccc23)cc1 | null | null | null |
53,890 | ord_dataset-053897d9b1744303b2fdfe3e796ca27b | null | 1979-01-01T00:04:00 | true | [CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].N1C=CC=CC=1.[O:15]([CH2:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:23](=[O:24])[CH2:22][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2] | O=C(Cl)COc1ccccc1 | CCN(CC)CCN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | First, 20 milliliters (0.05 mole) N,N-diethylethylene diamine, 50 milliliters methylene chloride, and 5.2 milliliters (0.065 mole) pyridine were combined in a flask. Next, 10.24 grams (0.06 mole) phenoxy acetyl chloride was added at -60° C. with stirring. The temperature was allowed to rise to 0° C. The reaction mixtur... | CCN(CC)CCNC(=O)COc1ccccc1 | null | 66.3 | null |
141,220 | ord_dataset-343f84c5bd164b25aeae96e1d828e768 | null | 1986-01-01T00:03:00 | true | [OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:14])[CH:9]=[C:8]2[C:3]=1[CH:4]([CH2:28][CH2:29][C:30]([O-])=[O:31])[CH2:5][CH:6]1[CH2:27][CH2:26][CH2:25][CH2:24][N:7]12>CCOCC>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH2:15][CH2:16][CH2:17][C:18]2[CH:... | CC(CCCc1ccccc1)Oc1cc(O)c2c(c1)N1CCCCC1CC2CCC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | null | A 125 ml., round bottomed flask equipped with a magnetic stirrer and nitrogen inlet is thoroughly flushed with dry nitrogen. Lithium aluminum hydride, 158 mg. (4.2 mmole) and 50 ml. of dry ethyl ether were added and the suspension stirred and cooled in an ice bath. To the cooled mixture is added slowly 1.89 g. (4.2 mmo... | CC(CCCc1ccccc1)Oc1cc(O)c2c(c1)N1CCCCC1CC2CCCO | null | null | null |
1,664,344 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | P(Br)(Br)[Br:2].[CH3:5][N:6]1[C:10]([CH2:11]O)=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[N:7]1>CCOCC>[Br:2][CH2:11][C:10]1[N:6]([CH3:5])[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)[CH:9]=1 | BrP(Br)Br | Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 16 | PBr3 (0.15 mL, 1.60 mmol) was added to a solution of alcohol 72 (0.205 g, 0.75 mmol) in Et2O (10 mL) at 0° C. The mixture was stirred at room temperature for 16 h, cooled to 0° C., quenched with ice and diluted with Et2O (100 mL). Chromatography of the organic portion on silica gel (eluting with CH2Cl2) gave 5-(bromome... | Cn1nc(-c2ccc(OC(F)(F)F)cc2)cc1CBr | null | 84.3 | null |
502,354 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [NH2:1][C:2]1[C:3]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:17][CH:16]=2)=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:29](=S)(OCC)[S-:30].[Na+]>C(O)C>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]... | CCOC(=S)[S-] | CCOC(=O)c1cccc(N)c1NCc1ccc(-c2ccccc2C#N)cc1 | null | [Na+] | 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 | A mixture of ethyl 3-amino-2-[(2′-cyanobiphenyl-4-yl)-methyl]aminobenzoate (5.6 g) and sodium O-ethyl dithiocarbonate (7.3 g) in ethanol (50 ml) was heated for 8 hours under reflux. The reaction mixture was concentrated and the residue was dissolved in water. The solution was adjusted to pH 3-4 with hydrochloric acid. ... | CCOC(=O)c1cccc2nc(S)n(Cc3ccc(-c4ccccc4C#N)cc3)c12 | null | 80.2 | null |
289,570 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[CH3:6][S:7](Cl)(=[O:9])=[O:8].C(N(CC)CC)C>CCOCC>[CH3:6][S:7]([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)(=[O:9])=[O:8] | CS(=O)(=O)Cl | OCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCOCC | null | null | null | null | null | null | null | null | null | 25 | null | Cyclopropylcarbinol (27.4 g; 0.373 mol) and methanesulfonyl chloride (47.56 g; 0.407 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (59 ml; 0.42 mol) is added dropwise over 45 min with external cooling so that the reaction temperature remained below -15° C. The reaction mixture was a... | CS(=O)(=O)OCC1CC1 | null | 104.2 | null |
127,249 | ord_dataset-3e4cbfe3ea40460399482e6cf2f9c894 | null | 1985-01-01T00:02:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([CH3:14])[N:3]=1.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21].[OH-].[Na+]>C(Cl)Cl>[CH3:14][C:4]1[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)(=[O:21])=[O:22])=[O:25])[N:7]... | O=C=NS(=O)(=O)c1cccs1 | COC(=O)COc1cc(C)nc(N)n1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 3 | To a dry stirred solution of 18 parts of methyl (2-amino-6-methylpyrimidin-4-yloxy)acetate in 300 parts of methylene chloride at ambient temperature was added 20 parts of 2-thiophenesulfonylisocyanate. The solution was allowed to stand for 3 hours and was then poured onto ice. The pH of the aqueous layer was adjusted t... | COC(=O)COc1cc(C)nc(NC(=O)NS(=O)(=O)c2cccs2)n1 | null | null | null |
473,274 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([OH:25])[C@@:10]2([N:22]=[N+:23]=[N-:24])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C:9](=[O:25])[C@@:10]2([N:22]... | CCOC(=O)[C@H]1[C@@H]2C[C@@H](O)[C@@](N=[N+]=[N-])(C(=O)OCc3ccccc3)[C@@H]21 | null | null | O=[Cr](=O)([O-])Cl | c1cc[nH+]cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 20 | To a solution of (1S,2R,3R,5R,6S)-2-Azido-3-hydroxy-bicyclo [3.1.0] hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII-1) (960 mg, 2.78 mmol) in DCM (18 mL) was added PCC (2.40 g, 50% on silica gel) at 0° C. and stirring was continued at 23° C. for 20 h. The reaction mixture was placed on a silica gel colum... | CCOC(=O)[C@H]1[C@@H]2CC(=O)[C@@](N=[N+]=[N-])(C(=O)OCc3ccccc3)[C@@H]21 | null | 78.2 | null |
879,441 | ord_dataset-3592bd645cd143ee8274cd0d834ae581 | null | 2009-01-01T00:05:00 | true | N[C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][CH:7]=1.S(=O)(=O)(O)[OH:12].N([O-])=O.[Na+].[OH-].[Na+]>O>[CH3:10][C:4]1[CH:3]=[C:2]([OH:12])[CH:7]=[N:6][C:5]=1[S:8][CH3:9] | O=S(=O)(O)O | CSc1ncc(N)cc1C | null | O=N[O-] | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 0.33 | A slurry of 5-amino-3-methyl-2-methylsulfanylpyridine (20.3 g, 132 mmol) in 20 wt percent aqueous sulfuric acid (170 mL) was cooled to −2° C. via an ice/salt water bath. A solution of sodium nitrite (9.1 g, 132 mmol) in water (30 mL) was added dropwise, maintaining the internal temperature at or below 1° C. After stirr... | CSc1ncc(O)cc1C | null | 68 | null |
61,731 | ord_dataset-d9fb402fe3e745c1893a29161cc5dda2 | null | 1980-01-01T00:01:00 | true | [CH2:1]([CH2:3][NH2:4])[OH:2].[ClH:5].[S:6]1(=[O:13])(=[O:12])[CH2:10][CH2:9][CH:8](N)[CH2:7]1>>[ClH:5].[OH:2][CH2:1][CH2:3][NH:4][CH:8]1[CH2:9][CH2:10][S:6](=[O:13])(=[O:12])[CH2:7]1 | NC1CCS(=O)(=O)C1 | NCCO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The procedure of Example 1 was repeated substituting 95 percent monoethanolamine (28.6 parts) for the ammonium hydroxide of Example 1. A sticky solid was filtered after treatment with hydrochloric acid, and upon drying in vacuo over P2O5 weighed 59.6 g. (78.5 percent of theory) m.p. 122°-124° C. | O=S1(=O)CCC(NCCO)C1 | null | null | null |
1,255,434 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [OH-].[Na+].CO.[CH:5]1([CH2:11][N:12]2[C:17](=[O:18])[C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][C:14]3[CH2:24][S:25][CH2:26][CH2:27][C:13]2=3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Cl>O>[CH:5]1([CH2:11][N:12]2[C:17](=[O:18])[C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]3[CH2:24][S:25][CH2:26][CH2:27][C:13]2=3)[CH2:6][CH2:7][... | CCOC(=O)c1cc2c(n(CC3CCCCC3)c1=O)CCSC2 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | 4M sodium hydroxide solution (15.2 mL, 60.8 mM) was added to a methanol (30 mL) solution of ethyl 1-cyclohexylmethyl-2-oxo-1,5,7,8,tetrahydro-2H-thiopyrano[4,3-b]pyridine-3-carboxylate (AA08, 8.16 g, 24.3 mmol), which had been obtained in Example 8, at room temperature, and the mixture was heated and refluxed for 30 mi... | O=C(O)c1cc2c(n(CC3CCCCC3)c1=O)CCSC2 | null | null | null |
1,008,648 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | [OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.O[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]2>>[O:33]=[C:28]1[CH2:27][CH2:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([O:1][CH2:2][CH2... | N#Cc1ccc(N(CCO)CC(F)(F)F)cc1C(F)(F)F | O=C1CCc2cc(O)ccc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized as described in Example 27B from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 15B) and 6-hydroxy-3,4-dihydro-2(1H)-quinolinone with the following exceptions: PPh3 was used instead of PBu3 and purification of the title compound consisted of flash chromatography (Et... | N#Cc1ccc(N(CCOc2ccc3c(c2)CCC(=O)N3)CC(F)(F)F)cc1C(F)(F)F | null | null | null |
1,582,902 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:36]([O:54][CH2:55][C@H:56](O)[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49][CH2:50][CH2:51][CH2:52][CH3:53].C... | [N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CCCCC/C=C\C/C=C\CCCCCCCCOC[C@H](O)CCCCCCCCC | null | CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | Triphenyl phosphine (14.4 g, 55 mmol) was dissolved in THF and cooled to 0° C. under nitrogen. Di-tertbutyl azodicarboxylate (13.7 g, 59.5 mmol) was added slowly and the reaction was stirred for 30 mins. Then the alcohol (20 g, 45.8 mmol) was added dropwise and allowed to stir for 10 mins, then diphenyl phosphorylazide... | CCCCC/C=C\C/C=C\CCCCCCCCOC[C@H](CCCCCCCCC)N=[N+]=[N-] | null | null | null |
1,249,811 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:13]([CH:15]3[CH:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=4[F:27])[C:18]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=4[F:37])([C:28]#[N:29])[CH:17]([CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[NH:16]3)=[O:14])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1>CO>[N... | CC(C)(C)CC1NC(C(=O)Nc2cccc(-c3nnn[nH]3)c2)C(c2cccc(Cl)c2F)C1(C#N)c1ccc(Cl)cc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [3-(1H-tetrazol-5-yl)-phenyl]-amide (690 mg) was resolved on a Berger SFC machine under 100 bar, 30° C. with 10% of methanol on an O.D. column gave two separated peaks. Peak 1, 256 m... | CC(C)(C)C[C@H]1N[C@H](C(=O)Nc2cccc(-c3nnn[nH]3)c2)[C@@H](c2cccc(Cl)c2F)[C@]1(C#N)c1ccc(Cl)cc1F | null | null | null |
1,554,529 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [F:1][CH:2]([F:17])[O:3][C:4]1[C:5]2[N:6]([C:10](I)=[C:11]([CH2:13][O:14][CH3:15])[N:12]=2)[CH:7]=[CH:8][CH:9]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]2=[C:23]([CH:39]=1)[O:24][CH2:25][C:26]1[CH:36]=[C:35]([CH:37]=[O:38])[CH:34]=[CH:33][C:27]=1/[C:28]/2=[C:29](/[CH3:32])\[C:30]#[N:31]>>[F:1][CH:2]([F:17])[O:3][C:4]1[C:5]2[... | C/C(C#N)=C1/c2ccc(C=O)cc2COc2cc(F)ccc21 | COCc1nc2c(OC(F)F)cccn2c1I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | [step 4] Using 8-(difluoromethoxy)-3-iodo-2-(methoxymethyl)imidazo[1,2-a]pyridine (700 mg, 1.98 mmol) obtained in step 3 and (E)-2-(3-fluoro-8-formyldibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (290 mg, 0.988 mmol) obtained in Reference Example 5, and in the same manner as in Reference Example 8F, step 4, (E)-2-(8-... | COCc1nc2c(OC(F)F)cccn2c1C(O)c1ccc2c(c1)COc1cc(F)ccc1/C2=C(\C)C#N | null | 77.6 | null |
511,964 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)#[N:2].[OH-:13].[Na+]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2)(=[O:13])[NH2:2] | [OH-] | N#Cc1ccc2c(c1)CC(=O)N2 | null | O=S(=O)(O)O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | A solution of 5-cyanooxindole (1.2 g, 7.6 mmol), (Tet. Let., 1987, 28, 4027), in 85% sulphuric acid (8 ml) was heated at 80° C. for 6 hours. The mixture was allowed to cool, poured into ice/water and the mixture was adjusted to pH5 with 2M sodium hydroxide solution. The solid product was collected by filtration, washed... | NC(=O)c1ccc2c(c1)CC(=O)N2 | null | 76 | null |
1,114,406 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]([NH2:19])=[C:13]3[CH:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]([NH2:19])=[C:13]3[CH:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1 | Nc1ncnc2c1cnn2-c1cccc([N+](=O)[O-])c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 42 | Title compound 10B, 1-(3-nitro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (1.0 g, 3.9 mmol) was added to 10% w/w palladium on carbon (0.1 g, 10% w/w) suspended in ethanol (300 ml). This was stirred for 42 hours at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered to remove the palla... | Nc1cccc(-n2ncc3c(N)ncnc32)c1 | null | null | null |
1,630,521 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | F[P-](F)(F)(F)(F)F.N1([O:17][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39]([C:42]2([C:45](N3CC[C@@]4(C5C=CC=CC=5C(=O)O4)C3)=[O:46])[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36]1[N:41]=[CH:40][C:39]([C:42]2([C:45]([OH:46])=[O... | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | O=C1O[C@]2(CCN(C(=O)C3(c4ccc(OCc5ccccc5)nc4)CC3)C2)c2ccccc21 | null | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the BOP coupling the desired product, (1R)-1′-({1-[6-(benzyloxy)pyridin-3-yl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one, was purified by prep-HPLC. LC/MS: 441.2 (M+H+). | O=C(O)C1(c2ccc(OCc3ccccc3)nc2)CC1 | null | null | null |
331,868 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | [CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:22]COC)=[C:6]([O:20][CH3:21])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2].Cl.O>C(O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:22])=[C:6]([O:20][CH3:21])[CH:7]=[C:8]2/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19]... | CCOC(=O)/C=C/c1cc(OC)c(OCOC)c2c(CC)cccc12 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 1.3 g of ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)propenoate in ethanol (10 ml) was added 1 ml of concentrated hydrochloric acid and stirred at room temperature for 2 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with wat... | CCOC(=O)/C=C/c1cc(OC)c(O)c2c(CC)cccc12 | null | 67 | null |
797,701 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].N12CCCN=C1CCCC[CH2:13]2.IC>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH3:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9] | O=[N+]([O-])c1ccc(O)cc1F | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | CI | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of 3-fluoro-4-nitrophenol (75 g, 0.48 mol) in acetone (700 mL) was cooled in an ice-water bath. 1,8-Diazabicyclo[5,4,0]undec-7-ene (145 g, 0.96 mol) was then added over ca. 5 min. Finally, iodomethane (135 g, 0.96 mol) was added over 10 min. The mixture was stirred at room temperature for 16 hr. Additional 1... | COc1ccc([N+](=O)[O-])c(F)c1 | null | null | null |
1,019,022 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(S[C:15](=[O:32])[CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][C:22]=1[Cl:31])[C:17](=[O:19])[CH3:18])(C)(C)C>>[Cl:31][C:22]1[CH:23]=[C:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=[CH:26][C:21]=1[CH2:20][CH:16]([C:17](... | CC(=O)C(Cc1ccc(S(C)(=O)=O)cc1Cl)C(=O)SC(C)(C)C | Nc1cc(O)ccc1F | null | null | null | null | null | null | null | 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 the method of Preparation 34b using 3-amino-4-fluorophenol and 2-(2-chloro-4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl ester. | CC(=O)C(Cc1ccc(S(C)(=O)=O)cc1Cl)C(=O)Nc1cc(O)ccc1F | null | null | null |
1,639,103 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-])=O.[N:22]1([C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[O:25]1[CH2:26][CH2:27][N:22]([C:28]2[CH:35]=[CH:34][C:31]([C:32]3[NH:19][... | O=C(Nc1ccc([N+](=O)[O-])c([N+](=O)[O-])c1)c1ccccc1 | O=Cc1ccc(N2CCOCC2)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 | Compound 259 was prepared according to the procedure similar to that described in Scheme III from 3,4-dinitro-N-benzoylaniline and 4-morpholinylbenzaldehyde. [M+H]+ calcd for C24H22N4O2: 399.18; found: 398.99. | O=C(Nc1ccc2[nH]c(-c3ccc(N4CCOCC4)cc3)nc2c1)c1ccccc1 | null | null | null |
1,102,927 | ord_dataset-375a420ee9b042918ddca20f02df37d3 | null | 2011-01-01T00:11:00 | true | CS(Cl)(=O)=O.C(N(CC)CC)C.O[C@H:14]1[CH2:23][C@@H:22]2[N:17]([C:18](=[O:24])[CH2:19][CH2:20][CH2:21]2)[C@H:16]([C:25]2[CH:30]=[C:29]([F:31])[C:28]([F:32])=[C:27]([F:33])[CH:26]=2)[CH2:15]1>C(Cl)Cl>[F:31][C:29]1[CH:30]=[C:25]([C@@H:16]2[CH:15]=[CH:14][CH2:23][C@@H:22]3[N:17]2[C:18](=[O:24])[CH2:19][CH2:20][CH2:21]3)[CH:2... | O=C1CCC[C@@H]2C[C@H](O)C[C@@H](c3cc(F)c(F)c(F)c3)N12 | null | null | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 2 | Methanesulfonyl chloride (776 μL) and triethylamine (2.79 mL) were added to a solution of (6S*,8S*,9aR*)-8-hydroxy-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one (1.0 g) in methylene chloride (20 mL) under ice-cooling, and the reaction solution was stirred at room temperature for two hours. The solvent was removed ... | O=C1CCC[C@@H]2CC=C[C@@H](c3cc(F)c(F)c(F)c3)N12 | null | 72.5 | null |
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