original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,630,430 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C([O:8][C:9](=[O:62])[C@:10]([CH3:61])([CH2:53][O:54][CH:55]1[CH2:60][CH2:59][CH2:58][CH2:57][O:56]1)[CH2:11][C@H:12]([NH:26][C:27]([C:29]1[N:30]=[N:31][N:32](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=1)=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)C1... | C[C@@](COC1CCCCO1)(C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)nn1)C(=O)OCc1ccccc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | (2S,4R)-5-Biphenyl-4-yl-2-methyl-2-(tetrahydropyran-2-yloxymethyl)-4-[(1-trityl-1H-1,2,3-triazole-4-carbonyl)amino]pentanoic acid benzyl ester (7.5 g, 9.1 mmol) was combined with EtOAc (80 mL, 800 mmol). The resulting clear solution was purged with nitrogen and 10% Pd/C (0.05:0.45, Palladium:carbon black, 1.0 g, 0.94 m... | C[C@@](COC1CCCCO1)(C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1c[nH]nn1)C(=O)O | null | 156.2 | null |
481,313 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:44]([F:49])([F:48])C([O-])=O.[Na+].O>COCCOCCOC>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21]... | O=CCOCCCCOc1c(Cl)cc(OCC=C(Cl)Cl)cc1Cl | O=C([O-])C(F)(F)Cl | null | [Na+] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | COCCOCCOC | null | null | null | null | null | null | null | null | null | 60 | 1.5 | A mixture of 1.21 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 0.87 g of triphenylphosphine and 10 ml of diglyme was stirred at 160° C., to which a solution (5 ml) of 0.69 g of sodium chlorodifluoroacetate in diglyme heated to 60° C. was added dropwise. After stirring at 160° C. for ... | FC(F)=CCOCCCCOc1c(Cl)cc(OCC=C(Cl)Cl)cc1Cl | null | 16 | null |
670,347 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:11][C:10]1[C:2]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)=[C:3]([CH:7]=[C... | COC(=O)c1ccc(N)cc1 | O=C(O)c1ccc(F)c(F)c1F | null | C[Si](C)(C)[N-][Si](C)(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | 2,3,4-Trifluorobenzoic acid and methyl 4-aminobenzoate were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B, to afford after workup, crude 3,4-difluoro-2-[[4-(methoxycarbonyl)-phenyl]amino]benzoic acid as a cream solid. This material was then coupled directly with 2-(amin... | COC(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)cc1 | null | null | null |
764,894 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3O)[C:6]=2[N:7]=1.O.CC#N.[C:25](OC(C)(C)C(Br)=O)(=[O:27])C.C([O-])(O)=O.[Na+]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([O:27][CH3:25])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@H:14... | Nc1nc(Cl)c2ccn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | CC(=O)OC(C)(C)C(=O)Br | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC#N | null | null | null | null | null | null | null | null | null | 25 | 2 | To a mixture of 2-amino-7-(β-D-ribofuranosyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g, 6.0 mmol) in acetonitrile (80 mL) were added a solution of H2O/CH3CN (1:9, 1.08 mL) and then α-acetoxyisobutyryl bromide (3.5 mL, 24 mmol). After 2 h stirring at room temperature, saturated aqueous NaHCO3 (170 mL) was added and t... | COc1nc(N)nc2c1ccn2[C@@H]1O[C@H](CO)[C@H]2O[C@H]21 | null | 115 | null |
605,748 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21](=[O:42])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[O:31])=[C:25]([O:40][CH3:41])[CH:24]=1)[CH2:16][CH2:15][CH2:14]2)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].O.[OH-]... | COC(=O)[C@H](Cc1ccc2c(c1)CCCN2C(=O)Cc1ccc(NC(=O)Nc2ccccc2C)c(OC)c1)NC(C)=O | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 25 | 3 | A solution of methyl (S) 2-acetylamino-3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate [220 mg, Reference Example 4(1)] in dioxane (3 ml) was treated with a solution of lithium hydroxide hydrate (50 mg) in water (1 ml). The mixture was stirred at room temperature for 3... | COc1cc(CC(=O)N2CCCc3cc(CC(NC(C)=O)C(=O)O)ccc32)ccc1NC(=O)Nc1ccccc1C | null | 9.8 | null |
674,954 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([C:14]#[N:15])=[CH:4][N:3]=1.[CH:16]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25])([CH3:18])[CH3:17].Cl>CC(O)CC>[C:14]([C:5]1[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)... | CC(C)NCCCNS(=O)(=O)c1ccc(N)cc1 | N#Cc1cnc(Cl)nc1N1CCOCC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-5-cyano-4-morpholinopyrimidine (Method 55; 425 mg, 1.90 mmol), 4-[N-(3-isopropylaminopropyl)sulphamoyl]aniline (Method 1; 514 mg, 1.90 mmol) and 1M ethereal hydrogen chloride (189□l, 3.79 mmol) in 2-butanol (2 ml) was heated at 95° C. for 15 hours. The mixture was allowed to cool, silica was added and the vola... | CC(C)NCCCNS(=O)(=O)c1ccc(Nc2ncc(C#N)c(N3CCOCC3)n2)cc1 | null | 18.8 | null |
256,921 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | C[O:2][C:3]1[C:12]2[C:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]=2[C:6]([O:17]C)=[CH:5][CH:4]=1.[N+]([O-])(O)=O>O1CCOCC1.[Ag]=O>[CH3:13][C:11]1([CH3:14])[CH2:10][CH2:9][C:8]([CH3:15])([CH3:16])[C:7]2[C:6](=[O:17])[CH:5]=[CH:4][C:3](=[O:2])[C:12]1=2 | COc1ccc(OC)c2c1C(C)(C)CCC2(C)C | null | null | O=[Ag] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=[N+]([O-])O | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | To a solution of 17.42 g (0.07 mole) of 1,4-dimethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro naphthalene, obtained in Example VIa, in 340 cm3 of dioxane, cooled to +5° C., there are added, with stirring, 34.7 g (0.28 mole) of silver oxide, AgO(II), then rapidly drop-by-drop, 70 cm3 (0.42 mole) of 6N HNO3. | CC1(C)CCC(C)(C)C2=C1C(=O)C=CC2=O | null | null | null |
268,391 | ord_dataset-134cf2fa32ab464880d75db06c38f35a | null | 1993-01-01T00:05:00 | true | [CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[CH2:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[N:29][C:30](Cl)=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[CH2:15][CH2:14]1)[CH3:12]>C1(C)C=CC=CC=1.O>[CH2:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][C... | CCCCCCCO | CC[C@H]1CC[C@H](CCc2ccc(-c3ccc(Cl)nn3)cc2)CC1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | 0.5 | A solution of n-heptanol (3.5 g) in toluene (50 ml) was dropwise added to a suspension of sodium hydride (about 55%) (1.5 g) in toluene (50 ml). The mixture was agitated for 30 minutes, dropwise adding a solution of 3-(4-(2-(trans-4-ethylcyclohexyl)ethyl)phenyl)-6-chloropyridazine (5 g) obtained above, in toluene (100 ... | CCCCCCCOc1ccc(-c2ccc(CC[C@H]3CC[C@H](CC)CC3)cc2)nn1 | null | 59.6 | null |
120,806 | ord_dataset-1d493fcbd5494078b46e816998dcb991 | null | 1984-01-01T00:08:00 | true | [CH:1]([C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)=O.[O:21]=[C:22]([CH2:43][C:44]#[C:45][CH2:46][CH3:47])[CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:12]([O:11][C@@H:10]1[CH2:9][C@H:8]2[C@H:4]([CH2:5][C:6](... | CCC#CCC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | O=C[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 7.4 g of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (E. J. Corey et al., J. Chem. Soc., 91, 5675 (1969)) and 10.3 g of the phosphorane prepared in Example (23b) in 200 ml of absolute toluene is stirred at room temperature for 5.5 hours. The reaction solution is concentrated in vacu... | CCC#CCC(=O)/C=C/[C@@H]1[C@H]2CC(=O)O[C@H]2C[C@H]1OC(=O)c1ccccc1 | null | 98.1 | null |
382,623 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH:7]=[C:8]([N:13]=[N+]=[N-])[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:17]=[C:16]2[C:6]([CH:7]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[NH:13]2)=[CH:5][CH:4]=1 | COC(=O)C(=Cc1ccc(OC)cc1)N=[N+]=[N-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Toluene (185 ml) is added to methyl 4-methoxy-α-azidocinnamate (PREPARATION 61, 7.73 g) and the reaction is brought to reflux and maintained at reflux for 3 hr. Then the reaction is concentrated under reduced pressure and triturated with hexane. The solids are filtered and dried under reduced pressure to give the title... | COC(=O)c1cc2ccc(OC)cc2[nH]1 | null | null | null |
624,076 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | COC[O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH2:11][CH2:12][CH2:13][OH:14].Cl>C(O)C>[OH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH2:11][CH2:12][CH2:13][OH:14] | COCOc1cnccc1CCCO | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | 3-(3-Methoxymethoxypyridin-4-yl)-1-propanol (3.67 g, 18.6 mmol) obtained in Example 2 is dissolved in ethanol (100 ml), and thereto is added a 15% aqueous hydrochloric acid solution (20 ml), and the mixture is heated under reflux for 30 minutes. The reaction solution is concentrated under reduced pressure, and the resi... | OCCCc1ccncc1O | null | 73 | null |
1,739,415 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11](Cl)=[O:12].[CH3:14][CH:15]([CH3:26])[CH2:16][CH:17]([C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[C:11]([NH:21][C:20]1[CH:22]=[CH:23... | CC(C)CC(C)c1ccccc1N | Cn1nc(C(F)F)c(C(=O)Cl)c1Cl | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 20 | 8 | 0.458 g (2.00 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride is added to a mixture of 0.322 g (1.81 mmol) of 2-(4-methylpentan-2-yl)aniline and 0.377 g (2.72 mmol) of potassium carbonate in 30 mL of acetonitrile, and the mixture is stirred at 20° C. overnight. After the reaction has ended... | CC(C)CC(C)c1ccccc1NC(=O)c1c(C(F)F)nn(C)c1Cl | null | null | null |
786,683 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]2.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29]Br)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:31])[CH2:29][O:... | O=C(CBr)c1ccc(Br)cc1 | CCOC(=O)C1=Cc2cc(O)ccc2OC1C(F)(F)F | 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 | 70 | 2 | The mixture of ethyl 6-hydroxyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.0 g, 3.47 mmol), 2-(4-bromophenyl)-2-oxoethyl bromide (0.96g, 3.47mmol) and potassium carbonate (0.96 g, 6.94 mmol) in 4 mL of dry DMF was heated to 70° C. and shaken for two hrs, then at room temperature overnight. The solid was filtered,... | CCOC(=O)C1=Cc2cc(OCC(=O)c3ccc(Br)cc3)ccc2OC1C(F)(F)F | null | 38.6 | null |
1,595,311 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]1[C:9]2[CH2:8][O:7][C:6](=[O:10])[C:5]=2[S:4][CH:3]=1.[Br:11]Br>C(Cl)(Cl)Cl.ClCCl>[Br:11][C:3]1[S:4][C:5]2[C:6](=[O:10])[O:7][CH2:8][C:9]=2[C:2]=1[CH3:1] | BrBr | Cc1csc2c1COC2=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | ClCCl | null | null | null | null | null | null | null | null | null | null | null | In a 50 mL round bottom flask was added 3-methylthieno[2,3-c]furan-6-(4H)-one (130 mg, 0.843 mmol, 1.0 eq) and chloroform (5 mL). To above solution was added bromine (86 μL, 1.08 mmol, 2.0 eq) in chloroform. The reaction was heat to reflux for 3 hr, cooled down, diluted with dichloromethane, washed with water, diluted ... | Cc1c(Br)sc2c1COC2=O | null | null | null |
1,133,837 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | N1C=CN=C1.[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12]/[C:13]/2=[N:16]/[OH:17])=[CH:9][CH:8]=1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>C(Cl)Cl>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:17]/[N:16]=[C:13]1/[CH2:12][CH2:11][C:10]2[C:14]... | CC(C)[Si](Cl)(C(C)C)C(C)C | O/N=C1/CCc2ccc(Br)cc21 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of imidazole (11 g, 162 mmol) in 100 mL of dry DCM was added dropwise to a solution of (Z)-6-bromo-2,3-dihydro-1H-inden-1-one oxime (1C) (18.2 g, 81 mmol) and triisopropylsilyl chloride (23.3 g, 121.5 mmol) in solution in 40 mL of dry DCM. The reaction mixture was stirred for 16 hours at rt. It was then filt... | CC(C)[Si](O/N=C1/CCc2ccc(Br)cc21)(C(C)C)C(C)C | null | null | null |
940,398 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:2]([O:4][C@H:5]1[... | C1CCNCC1 | COC[C@H]1OC(=O)c2coc3c2[C@@]1(C)C1=C(C3=O)[C@@H]2CC[C@H](O)[C@@]2(C)C[C@H]1OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 50 mg (0.12 mmol) 17-hydroxywortmannin in 0.5 mL CH2Cl2 is added 20.4 mg (0.24 mmol) piperidine. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with Et2O to give 33 mg (53.3%) product as an orange powder. MS (ESI) m/z 516.25 (M+1). | COC[C@H]1OC(=O)/C(=C/N2CCCCC2)C2=C(O)C(=O)C3=C([C@H](OC(C)=O)C[C@@]4(C)C3CC[C@@H]4O)[C@]21C | null | 53.3 | null |
832,861 | ord_dataset-ec576c604a9d47258c87c732a043ec71 | null | 2008-01-01T00:08:00 | true | [P:1]([O:13][CH2:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[S:36][C:37]([CH2:40][C:41]([NH:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[F:50])=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:51][CH3:52])([O:8]C(C)(C)... | COc1cc2c(Nc3ncc(CC(=O)Nc4ccccc4F)s3)ncnc2cc1OCCCN1CCC[C@H]1COP(=O)(OC(C)(C)C)OC(C)(C)C | null | null | Cl | Nc1c(F)c(N)c(F)c(F)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | An analogous reaction to that described in example 28 but starting with di(tert-butyl) ((2S)-1-(3-((4-((5-(2-((2-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl phosphate (612 mg, 0.81 mmol) yielded the title compound (527 mg, 86% yield) as a yellow dih... | COc1cc2c(Nc3ncc(CC(=O)Nc4ccccc4F)s3)ncnc2cc1OCCCN1CCC[C@H]1COP(=O)(O)O | null | 100.6 | null |
142,641 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O>[Ni].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15] | O=[N+]([O-])c1ccccc1NCc1ccccn1 | null | null | [Ni] | 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 | 10 g of N-2-picolyl-o-nitroaniline are hydrogenated with Raney nickel in methanol at room temperature to give the o-phenylenediamine derivative which remains as an oil, after the catalyst has been filtered off and the solvent has been evaporated in vacuo. | Nc1ccccc1NCc1ccccn1 | null | null | null |
878,111 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:38])[CH2:12][N:13]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[N:15]([CH2:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:14]2=[O:37])[CH:5]=1.[C:40]([O:44][C:45]([N:47]1C=C(C2C=CC=C(N)C=2)... | COC(=O)c1cccc(NC(=O)CN2N=C(C3CCCCC3)c3ccccc3N(CC(=O)C(C)(C)C)C2=O)c1 | CC(C)(C)OC(=O)n1cnc(-c2cccc(N)c2)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 obtained by the method used in the preparation of 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic acid methyl ester (Example 1) except that 4-(3-amino-phenyl)-imidazole-1-carboxylic acid tert-butyl ester (prepared in three steps... | CN(C(=O)OC(C)(C)C)c1cccc(NC(=O)CN2N=C(C3CCCCC3)c3ccccc3N(CC(=O)C(C)(C)C)C2=O)c1 | null | null | null |
1,580,587 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])O[C:6]2=[O:11].Cl.[NH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[N:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:11] | COC(=O)CN | O=C1OC(=O)c2c(O)cccc21 | 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 | 4-Hydroxyisobenzofuran-1,3-dione (600 mg, 3.66 mmol) and methyl 2-aminoacetate hydrochloride (505 mg, 4.02 mmol) were finely dispersed on Montmorillonite K10 (powder, Sigma-Aldrich) (1.2 g) and the solid mixture was reacted under microwave irradiation at 150° C. for 30 minutes. Montmorillonite was washed with MeOH and ... | COC(=O)CN1C(=O)c2cccc(O)c2C1=O | null | 18.6 | null |
1,088,340 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [Br:1]Br.[F:3][C:4]1[CH:5]=[C:6]([C:14]2[S:18][C:17]([NH:19][C:20]3[CH:24]=[CH:23][NH:22][N:21]=3)=[N:16][C:15]=2[CH3:25])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]>C(Cl)(Cl)Cl.CO>[Br:1][C:24]1[C:20]([NH:19][C:17]2[S:18][C:14]([C:6]3[CH:7]=[CH:8][C:9]([S:10]([CH3:13])(=[O:12])=[O:11])=[C:4]([F:3])[CH:5]=3)=[C... | Cc1nc(Nc2cc[nH]n2)sc1-c1ccc(S(C)(=O)=O)c(F)c1 | BrBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | CO | null | null | null | null | null | null | null | null | null | null | null | Bromine (0.012 ml, 0.23 mmol) in chloroform (0.5 ml) is added dropwise to a stirred solution of [5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-(1H-pyrazol-3-yl)-amine (69) (0.10 g, 0.23 mmol) in chloroform (1 ml) and methanol (2 ml). After stirring at room temperature for 1 hour the hydrobromide salt of ... | Cc1nc(Nc2n[nH]cc2Br)sc1-c1ccc(S(C)(=O)=O)c(F)c1 | null | null | null |
504,237 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [CH2:1]([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:23]([NH:25][NH:26][CH2:27][CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:24])[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:37]1([CH2:42][C:43](O)=[O:44])[CH:41]=... | O=C(O)Cn1cncn1 | CCC(CC)CNNC(=O)[C@H](CC(C)C)[C@H](C/C=C/c1ccccc1)C(=O)NOCc1ccccc1 | null | null | null | null | null | null | null | 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 manner analogous to that described in Example 8 from (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2-ethylbutyl)-4-methylvalerohydrazide and using 1,2,4-triazole-1-acetic acid in place of N-tert-butoxycarbonyl-β-alanine there was obtained (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2-... | CCC(CC)CN(NC(=O)[C@H](CC(C)C)[C@H](C/C=C/c1ccccc1)C(=O)NOCc1ccccc1)C(=O)Cn1cncn1 | null | null | null |
1,428,409 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | CC([N:5]([C@@H:9]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([O:30][CH3:31])[CH:24]=2)=[CH:18][CH:17]=1)=[O:14])[CH:10]([CH3:12])[CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14... | COc1cc(Oc2ccc(NC(=O)[C@@H](C(C)C)N(C(=O)[O-])C(C)(C)C)cc2)ccc1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 1,1-dimethylethyl((1R)-2-methyl-1-{[(4-{[4-methyl-3-(methyloxy)phenyl]oxy}phenyl)amino]carbonyl}propyl)carbamate (Intermediate 82, 110 mg) in dry dichloromethane (3 mL), TFA (1 mL, 12.98 mmol) was added and the reaction mixture was stirred for 1 hour at room temperature. The solvent and the excess of T... | COc1cc(Oc2ccc(NC(=O)[C@H](N)C(C)C)cc2)ccc1C | null | 80.5 | null |
1,015,232 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | Cl[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:4][CH:3]=1.O.NN>C1COCC1.[Ni]>[S:6]1[CH:2]=[CH:3][N:4]=[C:5]1[C:7]1[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=1 | O=[N+]([O-])c1cccc(-c2ncc(Cl)s2)c1 | null | null | [Ni] | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | To a solution of 5-chloro-2-(3-nitro-phenyl)-thiazole (20.0 g, 69.6 mmol) in THF (260 ml) was added hydrazine monohydrate (13.5 ml, 278 mmol) and Raney nickel (2 g). The resultant mixture was stirred at ambient conditions for 1 hour and then filtered through celite. The filtrate was evaporated to dryness and the filtra... | Nc1cccc(-c2nccs2)c1 | null | 86.4 | null |
749,547 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH2:1]([O:8][C:9]1[CH:20]=[C:19]2[C:12]([NH:13][CH:14]=[C:15]2[CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH:31]=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+].C(O)(=O)C(O)=O>CO.O>[CH2:1]([O:8][C:9]1[CH:20]=[C... | NCCc1c[nH]c2ccc(OCc3ccccc3)cc12 | O=Cc1cccc(Oc2ccccc2)c1 | null | O=C(O)C(=O)O | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 1 | Combine 5-benzyloxy tryptamine (1.23 g, 4.6 mmol), 3-phenoxybenzaldehyde (97%, 1.09 g, 5.53 mmol) and molecular sieves 4 A (1.0 g) and stir in methanol (15 mL) for 4 h. Filter the molecular sieves and wash several times with MeOH. To this MeOH solution, add portionwise NaBH4 (174 mg, 4.60 mmol), stir the resulting mixt... | c1ccc(COc2ccc3[nH]cc(CCNCc4cccc(Oc5ccccc5)c4)c3c2)cc1 | null | null | null |
581,536 | ord_dataset-60f3171f0342452f8814e7f294e2be8b | null | 2003-01-01T00:02:00 | true | C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([C:10]([O:12]C)=[O:11])[C@H:7]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C@@H:6]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:4].[OH-].[Li+].O.Cl>CO>[C:23]([O:22][C:20]([NH:19][C@H:6]1[C@@H:7]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:10]([OH:12])=[O:11])[... | COC(=O)[C@H]1C[C@@H](C(=O)OC)[C@H](CNC(C)=O)[C@@H]1NC(=O)OC(C)(C)C | null | null | Cl | [Li+] | [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 | (±)-(1S,2S,3R,4R)-2-(t-Butyloxycarbonylamino)-3-(acetamidomethyl)-cyclopentane-1,4-dicarboxylic acid dimethyl ester (255 mg, 0.68 mmole) and lithium hydroxide (2.2 equivalents) in 15 mL of 4:1 methanol:water were reacted at room temperature for 2 hours. The reaction was acidified with dilute HCl and extracted with ethy... | CC(=O)NC[C@@H]1[C@H](NC(=O)OC(C)(C)C)[C@@H](C(=O)O)C[C@H]1C(=O)O | null | null | null |
1,599,121 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11](Cl)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:9][CH2:10][C:11]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:8])=[O:12] | Oc1ccc(Cl)cc1 | O=C(Cl)CCl | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 80 | 8 | (Ref: J. Org. Chem. 1955; 20; 813-818) A mixture of 4-chlorophenol (5 g; 39.0 mmol) and chloroacetyl chloride (3.41 mL; 42.8 mmol) was heated to 80° C. for 2.5 hours. Mixture cooled to 30° C. and aluminum chloride (5.2 g; 39.0 mmol) was added over 30 minutes. Mixture heated to 130° C. for 15 hours. Mixture cooled under... | O=C(CCl)c1cc(Cl)ccc1O | null | 63 | null |
1,200,019 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | C[O-].[Na+].Cl[CH2:5][C:6]12OC(=O)C(=O)[N:7]1[CH2:8][CH2:9][C:10]1[C:15]2=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=1.C[CH2:24][O:25]C(C)=O.O>CO>[CH2:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][N:7]=[C:6]2[CH2:5][O:25][CH3:24])=[CH:11][CH:12]=1)[CH3:17] | CCOC(C)=O | CCc1ccc2c(c1)C1(CCl)OC(=O)C(=O)N1CC2 | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Sodium methoxide (9.46 g) was added to a suspension of 10b-(chloromethyl)-9-ethyl-6,10b-dihydro-5H-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione (14.0 mL) in MeOH (140 mL) under ice-cooling. The mixture was stirred at room temperature for 0.5 hours and then heated under reflux for 3 hours. EtOAc and water were added to the... | CCc1ccc2c(c1)C(COC)=NCC2 | null | null | null |
1,413,276 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [C:1]([C@@H:3]([NH:5][C:6](=[O:12])OC(C)(C)C)[CH3:4])#[N:2].[CH2:13]([C:23]1[CH:31]=[CH:30][C:26](C(O)=O)=[CH:25][CH:24]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[C:1]([C@@H:3]([NH:5][C:6](=[O:12])[C:26]1[CH:25]=[CH:24][C:23]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH... | CCCCCCCCCCc1ccc(C(=O)O)cc1 | C[C@@H](C#N)NC(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | General procedure D was used to deprotect 0.198 g (1.2 mmols) of 4. The product was immediately carried on using general procedure F and coupled to 1.2 mmols of 7. The title product was purified with flash chromatography using a solvent system of ethyl acetate and hexanes (1:3) to yield 0.2 g (0.63 mmols). 1H NMR (500 ... | CCCCCCCCCCc1ccc(C(=O)N[C@@H](C)C#N)cc1 | null | null | null |
906,088 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [CH2:1]([O:8][C:9](=[O:29])[CH:10]([O:17][N:18]1C(=O)C2C(=CC=CC=2)C1=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CCO>[CH2:1]([O:8][C:9](=[O:29])[CH:10]([O:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C(OCc1ccccc1)C(ON1C(=O)c2ccccc2C1=O)c1ccccc1 | null | null | NN | 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 solution of the compound from Step 4a (3.8 g, 9.8 mmol) and hydrazine (0.64 mL, 20 mmol) in EtOH (30 mL) was stirred at room temperature for 2 hours. The reaction mixture was filtered. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic phase was washed with brine, dried (Na2SO4), filter... | NOC(C(=O)OCc1ccccc1)c1ccccc1 | null | 95.2 | null |
1,738,428 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [C:1]([C:3]1[CH:4]=[N:5][N:6]([CH3:8])[CH:7]=1)#[CH:2].[Br:9][C:10]1[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:13](I)=[CH:12][N:11]=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:9][C:10]1[N:11]=[CH:12][C:13]2[CH:2]=[C:1]([C:3... | C#Cc1cnn(C)c1 | CS(=O)(=O)Nc1cc(Br)ncc1I | null | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | [Cu]I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 60 | null | 4-Ethynyl-1-methyl-1H-pyrazole (20) (4.11 g, 38.7 mmole) was dissolved in DMF (95 mL) and N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide 8 (12.18 g 32.3 mmole) was added. To the solution was added triethylamine (19.6 mL, 14.1 g 139 mmole) and copper(I) iodide (214 mg 1.12 mmole). The reaction was sealed and flushed w... | Cn1cc(-c2cc3cnc(Br)cc3n2S(C)(=O)=O)cn1 | null | 45.2 | null |
1,364,824 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [CH:1]([C:3]1[N:7]([CH3:8])[CH:6]=[N:5][C:4]=1[C:9]#[N:10])=O.Cl.[NH2:12][CH2:13][CH:14]([C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:22]=1[F:29])[CH2:15][C:16](OCC)=[O:17]>>[CH3:8][N:7]1[C:3]([CH2:1][N:12]2[CH2:13][CH:14]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:22]=3[F:29])[CH2:15][C:16]2=[O:17]... | Cn1cnc(C#N)c1C=O | CCOC(=O)CC(CN)c1cc(F)cc(F)c1F | 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 | 1-methyl-5-{[2-oxo-4-(2,3,5-trifluorophenyl)pyrrolidin-1-yl]methyl}-1H-imidazole-4-carbonitrile 127 is prepared according to the method described in 10.1 starting from 5-formyl-1-methyl-1H-imidazole-4-carbonitrile x86 and ethyl 4-amino-3-(2,3,5-trifluorophenyl)butanoate hydrochloride x60. | Cn1cnc(C#N)c1CN1CC(c2cc(F)cc(F)c2F)CC1=O | null | 25.8 | null |
733,098 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>>[C:15]1([N:6]2[C:5]3[CH:21]=[CH:22][C:2]([N:1]([S:31]([C:28]4[CH:27]=[... | COc1ccc(S(=O)(=O)Cl)cc1 | Nc1ccc2c(c1)nc(-c1ccccc1)n2-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 | 5-Amino-1,2-diphenyl-1H-benzimidazole was reacted with 4-methoxybenzenesulfonic acid chloride according to general operating instructions 13. | COc1ccc(S(=O)(=O)N(c2ccc3c(c2)nc(-c2ccccc2)n3-c2ccccc2)S(=O)(=O)c2ccc(OC)cc2)cc1 | null | null | null |
1,329,555 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([CH2:40][C:41](O)=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:44][CH2:45][CH3:46]... | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)N1CCC(CC(=O)O)CC1 | CNc1cccc(C)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 | In a manner analogous to the method described in example 163, {1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-acetic acid was coupled with N-methyl-N-m-tolylamine (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated ... | CCOc1cc(C(C)(C)C)ncc1C1=N[C@@](C)(c2ccc(Cl)cc2)[C@@](C)(c2ccc(Cl)cc2)N1C(=O)N1CCC(CC(=O)N(C)c2cccc(C)c2)CC1 | null | null | null |
694,792 | ord_dataset-a7baa616c65d42559e25ca0ba61e0744 | null | 2006-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=1... | O=C1NC(Cc2cccc(OC(F)(F)C(F)F)c2)C(c2cccc(F)c2)O1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of (4RS,5SR)-5-(3-fluorophenyl)-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (3.30 g, 8.52 mmol) in ethanol (12 ml) was added 8N aqueous sodium hydroxide solution (5.3 ml, 42 mmol), and the mixture was heated under reflux for 5 hrs. The reaction solutions was concentrated, diluted with wat... | NC(Cc1cccc(OC(F)(F)C(F)F)c1)C(O)c1cccc(F)c1 | null | null | null |
351,628 | ord_dataset-127eb5fdd5b4402e92b51d0b55a5dcb5 | null | 1997-01-01T00:01:00 | true | [C:1]([O-:4])(=[O:3])[CH3:2].[K+].[OH:6][C@@H:7]1[C@@H:31]([N:32]2[CH2:37][CH2:36][O:35][C:34]([CH3:39])([CH3:38])[CH2:33]2)[CH2:30][C@@:29]2([CH3:40])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:41])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C:17](=[O:24])[CH2:18]OS(C)(=O)=O)[CH2:8]1.O>C(O)C>[C... | CC(=O)[O-] | CC1(C)CN([C@H]2C[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C(=O)COS(C)(=O)=O)CC[C@@H]43)C[C@@H]2O)CCO1 | null | [K+] | 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 | Anhydrous potassium acetate (470 mg) was added to (2β,3α,5α)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)-21-[(methylsulfonyl)oxy]pregnan-20-one (1.0 g) in ethanol (15 ml) and the solution was heated under reflux for 1.5 h. The reaction mixture was poured into water (150 ml) and the precipitated solid was filtered off, was... | CC(=O)OCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](N5CCOC(C)(C)C5)C[C@]4(C)[C@H]3CC[C@]12C | null | 35.4 | null |
1,270,903 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:18]>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:18])=[CH:10][CH:9]=1 | Oc1ccc(Br)cc1 | COc1ccc(C(=O)CBr)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | 24 g of potassium carbonate are added to a solution of 20 g (0.115 mol) of 4-bromophenol and 26.5 g (0.115 mol) of 2-bromo-4′-methoxyacetophenone in 400 of acetonitrile, and the reaction mixture is heated under reflux for five hours. The precipitate is subsequently filtered off, the filtrate is evaporated to dryness, t... | COc1ccc(C(=O)COc2ccc(Br)cc2)cc1 | null | 96.1 | null |
670,170 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:16][CH2:15][CH:14]([NH:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>[Pd]>[C:5]1([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[... | O=S(=O)(NC1CCC(c2cc(F)ccc2F)(S(=O)(=O)c2ccc(Cl)cc2)CC1)C(F)(F)F | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 16 | A solution of the product from Example 47 (0.28 g, 0.6 mmol) was flushed with nitrogen, 10% palladium on carbon (0.03 g, 10% w/w) was added, and the mixture was hydrogenated at 40 psi for 16 hours. Filtration and evaporation in vacuo gave the product (0.28 g, 99%). 1H NMR (CDCl3, 400 MHz): 1.61-1.68 (2H, m), 2.03-2.07 ... | O=S(=O)(NC1CCC(c2cc(F)ccc2F)(S(=O)(=O)c2ccccc2)CC1)C(F)(F)F | null | 96.5 | null |
1,274,819 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11]Br)=[CH:8][C:9]=1[Cl:10])=[O:4].C([O-])(O)=[O:14].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][OH:14])=[CH:8][C:9]=1[Cl:10])=[O:4] | O=C([O-])O | COC(=O)c1sc(CBr)cc1Cl | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | 115 | null | A mixture of 5-Bromomethyl-3-chloro-thiophene-2-carboxylic acid methyl ester (3.8 g, 14.1 mmol) and NaHCO3 (20 g, 238 mmol) in DMSO (100 ml) was heated at 115° C. for 4 h. The reaction mixture was cooled. The reaction mixture was diluted with water and extracted with DCM (3×100 mL), washed with brine, dried over sodium... | COC(=O)c1sc(CO)cc1Cl | null | 44.6 | null |
1,502,005 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1.[ClH:24].O1CCOCC1>ClCCl>[ClH:24].[ClH:24].[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1 | CC(C)(C)OC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2Br)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1COCCO1 | null | null | null | null | null | null | null | null | null | 20 | 3 | A solution of tert-butyl 4-(2-bromo-4-nitrophenyl)piperazine-1-carboxylate (2.3 g, 5.9 mmol) in dichloromethane (15 mL) was treated with 4 M HCl in 1,4-dioxane (15 mL, 59 mmol) and stirred at 20° C. for 3 h. The reaction mixture was concentrated, diluted with a minimal amount of methanol (˜15 mL), and added dropwise to... | O=[N+]([O-])c1ccc(N2CCNCC2)c(Br)c1 | null | 89 | null |
78,329 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].O>C(O)(=O)C>[Br:1][C:12]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH... | BrBr | CCOC(=O)c1[nH]c2ccc(Cl)cc2c1-c1ccccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(=O)O | null | null | null | null | null | null | null | null | null | 25 | 16 | Add 1.0 ml of bromine to 4.6 g of ethyl 5-chloro-3-(2-fluorophenyl)indole-2-carboxylate in 250 ml of glacial acetic acid. Stir for 16 hours at room temperature, add water and collect the precipitate. Ws the precipitate with warm methanol. Collect the dry ethyl 6-bromo-5-chloro-3-(2-fluorophenyl)indole-2-carboxylate, m.... | CCOC(=O)c1[nH]c2cc(Br)c(Cl)cc2c1-c1ccccc1F | null | null | null |
859,725 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]([C:10]1[CH:14]=[C:13]([NH2:15])[O:12][N:11]=1)([CH3:9])([CH3:8])[CH3:7].N1C=CC=CC=1>ClCCl>[C:6]([C:10]1[CH:14]=[C:13]([NH:15][C:3](=[O:4])[CH2:2][Cl:1])[O:12][N:11]=1)([CH3:9])([CH3:8])[CH3:7] | O=C(Cl)CCl | CC(C)(C)c1cc(N)on1 | 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 | 0 | 2 | Chloroacetic acid chloride (0.25 ml; 3.14 mmol) is dropped slowly into a stirred solution of 3-t-Butyl-5-amino isoxazole (400 mg; 2.85 mmol) in pyridine (0.3 ml; 3.71 mmol) and dichloromethane (2 ml), cooled to 0° C. Stirring is continued for 2 h at room temperature. The reaction mixture is diluted with dichloromethane... | CC(C)(C)c1cc(NC(=O)CCl)on1 | null | 97.2 | null |
435,968 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [CH3:1][C:2]([CH3:16])([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[CH3:15])=[O:6])[CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:24][C:25]([NH2:27])=[O:26]>CN(C=O)C>[CH3:3][C:2]([CH3:16])([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:24][C:25]([NH2:27])=[O:26])=[CH:10][C:9]=1[CH3:15])=[O:... | NC(=O)CBr | Cc1cc(O)ccc1NC(=O)OC(C)(C)C | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a 200 mL round bottomed flask with a stirring bar, and an argon inlet was added 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenol (5.00 g, 22.39 mmot), Cs2CO3 (14.59 g, 44.78 mmol), DMF (50 mL), and bromoacetamide (3.24 g, 23.51 mmol). This mixture was stirred vigorously at ambient temperature for 24 h. The mixture... | Cc1cc(OCC(N)=O)ccc1NC(=O)OC(C)(C)C | null | 78.2 | null |
705,904 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | C([S:4][C@@H:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([C:11]([O:13]C)=[O:12])[CH2:6]1)(=O)C.[ClH:15]>O>[ClH:15].[SH:4][C@@H:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([C:11]([OH:13])=[O:12])[CH2:6]1 | COC(=O)[C@@H]1C[C@H](SC(C)=O)CN1C | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 2.5 | 1 | A mixed solution of methyl (2S,4S)-4-acetylthio-1-methyl-2-pyrrolidinecarboxylate (10.7 g), concentrated hydrochloric acid (14.9 g) and water (16 mL) was stirred at from 75 to 85° C. for 5 hours. After completion of the reaction, the water in the reaction mixture was removed by distillation under reduced pressure. Acet... | CN1C[C@@H](S)C[C@H]1C(=O)O | null | 94.5 | null |
179,502 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | Cl.C([NH:4][C@H:5]([C:10]([NH:12][C@H:13]([C:21]([OH:23])=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH2:6][C:7](=[O:9])[OH:8])=O.[CH2:24](N(CC)CC)C>CO>[CH3:24][O:8][C:7](=[O:9])[CH2:6][CH:5]1[C:10](=[O:11])[NH:12][CH:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21](=[O:23])[NH:4... | CCN(CC)CC | O=CN[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | null | To a solution having 9.6 g of hydrogen chloride dissolved in 400 ml of methanol was fed 61.6 g of N-formyl-α-L-aspartyl-L-phenylalanine and the resulting mixture was reacted at 50°-60° C. for 6 hours. The resulting reaction solution was cooled to room temperature, added dropwise with 30.4 g of triethylamine, and then s... | COC(=O)CC1NC(=O)C(Cc2ccccc2)NC1=O | null | 72.8 | null |
1,675,895 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH2:14]1CCN2C(=NCCC2)CC1.IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:13])[C:10]([O:12][CH3:14])=[O:11])=[CH:6][CH:7]=1 | C1CCC2=NCCCN2CC1 | O=C(O)C(=O)Cc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CI | null | null | null | null | null | null | null | null | null | null | 2.5 | To a solution of 3-(4-bromophenyl)-2-oxopropionic acid (70.0 mg, 0.288 mmol) in DMF (2 mL) at 0° C. was added DBU (72.2 mg, 0.288 mmol) and iodomethane (204 mg, 1.440 mmol). The reaction mixture was stirred for 2.5 hours at the same temperature. The reaction was acidified with 1 M HCl and extraction with ether (3×25 mL... | COC(=O)C(=O)Cc1ccc(Br)cc1 | null | 68 | null |
1,048,577 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | O.S(=O)(=O)(O)O.[CH2:7]([N:14]1[CH2:21][CH:20](O)[CH2:19][N:18](S(C2C=CC=CC=2)(=O)=O)[CH2:17][CH:16]([OH:32])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:7]([N:14]1[CH2:15][CH:16]2[O:32][CH:20]([CH2:19][NH:18][CH2:17]2)[CH2:21]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1 | O=S(=O)(c1ccccc1)N1CC(O)CN(Cc2ccccc2)CC(O)C1 | null | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | O | null | null | null | null | null | null | null | null | null | 95 | null | Water (11.2 mL) and concentrated sulfuric acid (24.5 mL) were added to 5-benzyl-3,7-dihydroxy-1-phenylsulfonyl-1,5-diazacyclooctane (2.92 g, 7.76 mmol; see step (ii) above). The reaction mixture was heated for 24 hours at 95° C. The temperature was adjusted to 60° C., and toluene (40 mL) was added. Sodium hydroxide sol... | c1ccc(CN2CC3CNCC(C2)O3)cc1 | null | null | null |
790,327 | ord_dataset-530502f8e61e455784f93c5faa45c94b | null | 2007-01-01T00:09:00 | true | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[C:3]=1[CH2:21][CH2:22][CH3:23].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20]... | CCCc1c(Cl)ncnc1Cn1ccnc1-c1cccc(F)n1 | [N-]=[N+]=[N-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 103 (2.25 mmol) and NaN3 (731 mg, 11.25 mmol) in DMF (15 ml) is heated at 70° C. in a sealed tube overnight. The solvent is removed in vacuo and water (10 ml) and EtOAc (10 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (2×10 ml). The combined extracts... | CCCc1c(Cn2ccnc2-c2cccc(F)n2)ncnc1N=[N+]=[N-] | null | null | null |
1,081,596 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][N:23]=2)[N:20]=1>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]([F:... | Cc1ccccc1N1CCNCC1 | FC(F)(F)c1nnc2ccc(Cl)nn12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1-(2-methylphenyl)piperazine and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine was allowed to react by General Synthetic Method 3. The crude product was purified by hplc using a Waters XTerra C18 column (5μ silica, 19 mm diameter, 100 mm length) eluted with decreasingly polar mixtures of wa... | Cc1ccccc1N1CCN(c2ccc3nnc(C(F)(F)F)n3n2)CC1 | null | null | null |
56,002 | ord_dataset-159c363342e44b539e7a5975c873e30d | null | 1979-01-01T00:05:00 | true | Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.[Na]>C(O)C>[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:17][CH:16]=2)=[C... | CCOC(=O)C(C)Br | Oc1ccc(Oc2ccc(Cl)cc2)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 | 20.9 g (0.115 mol) of ethyl 2-bromo-propionate are run over the course of 30 minutes into a hot solution of 23 g (0.1045 mol) of p-(p-chlorophenoxy)-phenol and 2.4 g (0.1045 mol) of sodium in 90 ml of anhydrous ethanol and the mixture is then heated to the reflux temperature for 2 hours. The inorganic salts are removed... | CCOC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2)cc1 | null | null | null |
671,472 | ord_dataset-e90cd41afe844e49875435eb99903799 | null | 2005-01-01T00:05:00 | true | [CH3:1][N:2]([CH3:10])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)=[O:4].Br[CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:15][CH2:14][CH2:13][CH2:12][N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3](=[O:4])[N:2]([CH3:10])[CH3:1] | OCCCBr | CN(C)C(=O)[C@@H]1CCCN1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of (S)-2(N,N-dimethylcarbamoyl)pyrrolidine (426 mg, 3 mmol), (Chem. pharm. Bull. 1973, 21, 2112-2116), 3-bromo-1-propanol (0.41 ml, 4.5 mmol) and potassium carbonate (829 mg, 6 mmol) in acetonitrile (6 ml) was heated at reflux for 8 hours. The mixture was allowed to cool and was partitioned between methylene ... | CN(C)C(=O)[C@@H]1CCCN1CCCO | null | 48.3 | null |
1,588,940 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | C(O[C:6]([N:8](C)[CH:9]([CH2:15][CH2:16][CH2:17][CH2:18][B:19]1[O:23]C(C)(C)C(C)(C)[O:20]1)[C:10]([O:12]CC)=[O:11])=O)(C)(C)C>Cl>[B:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH:9]([NH:8][CH3:6])[C:10]([OH:12])=[O:11])([OH:23])[OH:20] | CCOC(=O)C(CCCCB1OC(C)(C)C(C)(C)O1)N(C)C(=O)OC(C)(C)C | 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 | A solution of ethyl 2-(tert-butoxycarbonyl(methyl)amino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (59 mg) in aq 6 M HCl was heated to reflux for 16 h, concentrated to dryness and purified by preparative HPLC. The residue was redissolved in 2 N HCl and evaporated to give 6-borono-2-(methylamino)hexanoic ... | CNC(CCCCB(O)O)C(=O)O | null | 85.9 | null |
974,093 | ord_dataset-f886e51ba1484c76a94bce1482f1eab9 | null | 2010-01-01T00:07:00 | true | [NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][C@@H:18]([CH3:20])[O:17][C@@H:16]([CH3:21])[CH2:15]2)[N:11]=[C:10]([N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:25]=3[N:24]=[C:23]2[CH:33]([F:35])[F:34])[N:9]=1>O>[F:34][CH:33]([F:35])[C:23]1[N:22]([C:10]2[N:11]=[C:12]([N:... | C1COCCN1 | COc1cccc2c1nc(C(F)F)n2-c1nc(Cl)cc(N2C[C@@H](C)O[C@@H](C)C2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 80 | 0.5 | Morpholine (275 ml, 3.15 mol) was added to 4-chloro-2-(2-difluoromethyl-4-methoxybenzimidazol-1-yl)-6-(cis-2,6-dimethylmorpholino)pyrimidine (14.4 g, 34 mmol) thus obtained, and stirred at room temperature for 30 minutes and further at 80° C. for 30 minutes. Water was added to the reaction solution, and the precipitate... | COc1cccc2c1nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2C[C@@H](C)O[C@@H](C)C2)n1 | null | 84.9 | null |
159,514 | ord_dataset-41c90677d90b4fa5836ab66e2f5b4f51 | null | 1987-01-01T00:06:00 | true | [C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH:14]=[O:15])=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:23]>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:14]([OH:23])=[O:15])=[C:6]([CH2:18][CH... | CCCc1c(OCCCC#CC=O)ccc(C(C)=O)c1O | O=S(=O)(O)O | null | [Cr+6] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | To 0.58 g of chromium trioxide in 8 ml of 10N sulfuric acid cooled at 0° was added a solution of 1.51 g of 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hexynal in 15 ml of acetone over 30 minutes with stirring. The reaction mixture was allowed to warm to 25° over 30 minutes and then concentrated in vacuo to remove the acet... | CCCc1c(OCCCC#CC(=O)O)ccc(C(C)=O)c1O | null | 40 | null |
1,349,398 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:26]2[CH2:27][CH2:28][O:29][C:30](=[O:33])[N:31]([CH3:32])[C:25]=2[CH:24]=[CH:23][C:22]=1[O:34][CH3:35]>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=... | COc1ccc2c(c1N)CCOC(=O)N2C | CNC(=O)c1ccccc1Nc1nc(Cl)ncc1Cl | null | null | null | null | null | null | null | 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 an analogous manner to Example 1513, the product was prepared from 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 1-Amino-2-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product was isolated as a light yellow solid (4.0 mg, 4%). mp: 160° C. followed by solidification and melt at 25... | CNC(=O)c1ccccc1Nc1nc(Nc2c(OC)ccc3c2CCOC(=O)N3C)ncc1Cl | null | 4 | null |
329,953 | ord_dataset-2c460e2ef9934444aaf26fec1f75741f | null | 1996-01-01T00:05:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=1)([O-])=O.Cl[Sn]Cl>Cl>[NH2:1][C:4]1[CH:5]=[C:6]([C:9]([OH:11])=[O:10])[S:7][CH:8]=1 | O=C(O)c1cc([N+](=O)[O-])cs1 | null | null | Cl | Cl[Sn]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 | 25 | 6 | 4-Nitro-2-thiophenecarboxylic acid (1 g, 5.7 mmol) was added with stirring to a solution of SnCl2. 2H2O (3.25 g, 14.4 mmol) in concentrated HCl (10 ml). The mixture was stirred for 6 hours at ambient temperature and purified by subjecting to chromatography on HP20SS resin, using water as eluant, to give the title compo... | Nc1csc(C(=O)O)c1 | null | 72.3 | null |
1,215,359 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH3:1][C:2]1([C:7]2[O:11][C:10]([CH2:12][N:13]3[CH:17]=[CH:16][C:15]([NH2:18])=[N:14]3)=[N:9][CH:8]=2)[O:6]CCO1.[C:19]1([C:25]2[O:29][CH:28]=[N:27][C:26]=2[C:30](O)=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:2]([C:7]1[O:11][C:10]([CH2:12][N:13]2[CH:17]=[CH:16][C:15]([NH:18][C:30]([C:26]3[N:27]=[CH:28][O:29][C:... | CC1(c2cnc(Cn3ccc(N)n3)o2)OCCO1 | O=C(O)c1ncoc1-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 | Following general procedure B followed by C, starting from 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-oxazol-2-ylmethyl]-1H-pyrazol-3-ylamine and 5-phenyl-oxazole-4-carboxylic acid. LC-MS-conditions 02: tR=0.92 min; [M+H]+=378.55. | CC(=O)c1cnc(Cn2ccc(NC(=O)c3ncoc3-c3ccccc3)n2)o1 | null | null | null |
184,745 | ord_dataset-8537fa92abf34c849134600c0c2bbcc7 | null | 1989-01-01T00:02:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl[CH:26]1[CH2:31][O:30][C:29](=[O:32])[O:28][CH2:27]1>>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N... | O=C1OCC(Cl)CO1 | CC(C)(C)c1cc(-c2n[nH]c3ncccc23)cc(C(C)(C)C)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By using 3.2 g of the compound of Example 1 and 1.6 g of 5-chloro-2-oxo-1,3-dioxane, the reaction is carried out in a similar manner as Example 78 (i) to give 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-(2-oxo-1,3-dioxan-5-yl)-1H-pyrazolo-[3,4-b]pyridine. | CC(C)(C)c1cc(-c2nn(C3COC(=O)OC3)c3ncccc23)cc(C(C)(C)C)c1O | null | null | null |
773,096 | ord_dataset-8214eb8444a44dc2900ccb42dbeff15e | null | 2007-01-01T00:05:00 | true | [CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[N:25]1[C:33]2[C:28](=[CH:29][C:30]([C:34]3[N:38]=[CH:37][N:36]([C:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[... | O=C(O)C1CC1 | Nc1cccc(-c2nn(C3CCCCO3)c3ccc(-c4ncn(C(c5ccccc5)(c5ccccc5)c5ccccc5)n4)cc23)c1 | null | CCN=C=NCCCN(C)C | Cl | 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 cyclopropanecarboxylic acid (0.024 g, 0.274 mmol) in 2.5 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.057 g, 0.298 mmol). The reaction was stirred at room temperature for 10 min before 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-tri... | O=C(Nc1cccc(-c2nn(C3CCCCO3)c3ccc(-c4ncn(C(c5ccccc5)(c5ccccc5)c5ccccc5)n4)cc23)c1)C1CC1 | null | null | null |
429,615 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[N:10]([C:11](=[O:33])[C@@H:12]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6]1=[O:38].C([O-])(O)=O.[Na+].[CH:44]1[CH:49... | O=C(Cl)OCc1ccccc1 | COc1ccc(C[C@H](NC(=O)OCc2ccccc2)C(=O)N2CCN(CC(=O)O)C(=O)[C@@H]2CCCN)cc1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | In 100 ml of a 50% aqueous solution of dioxane was dissolved 3.8 g of (S,S)-3-(3-aminopropyl)-4-[2-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionyl]-2-oxopiperazine-1-acetic acid produced in Reference Example 33. To the solution was added 1.52 g of NaHCO3, to which was added dropwise, under ice-cooling, 1.24 ml of Z... | COc1ccc(C[C@H](NC(=O)OCc2ccccc2)C(=O)N2CCN(CC(=O)O)C(=O)[C@@H]2CCCNC(=O)OCc2ccccc2)cc1 | null | null | null |
1,065,384 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]=3[NH:13][C:12]2=[O:23])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=... | COC(=O)CBr | Cc1ccc(S(=O)(=O)n2c(=O)[nH]c3c([N+](=O)[O-])cccc32)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a stirred solution of 1-[(4-methylphenyl)sulfonyl]-4-nitro-1,3-dihydro-2H-benzimidazol-2-one from Step B (500 mg, 1.50 mmol) in DMF (50 mL) was added potassium carbonate (207 mg, 1.50 mmol) and the resulting mixture was stirred at ambient temperature for 10 min. Methyl bromoacetate (252 mg, 1.65 mmol) was added drop... | COC(=O)Cn1c(=O)n(S(=O)(=O)c2ccc(C)cc2)c2cccc([N+](=O)[O-])c21 | null | null | null |
1,504,098 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [N:1]([CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]([O:21]C)=[O:20])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[N+:2]=[N-:3].[OH-].[Na+]>CO.O1CCCC1>[N:1]([CH:4]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:5]1[CH:... | COC(=O)C1(c2ccc(COc3cccc(C(N=[N+]=[N-])c4ccccc4)c3)cc2)CC1 | 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 | 50 | 0.5 | To a stirred solution of methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate (0.569 g, 1.375 mmol) in methanol (12.9 mL) and tetrahydrofuran (5.1 mL), was added 2M aqueous sodium hydroxide (12.9 mL). The reaction was stirred at 50° C. for 3 hours 30 minutes and then at room temperature f... | [N-]=[N+]=NC(c1ccccc1)c1cccc(OCc2ccc(C3(C(=O)O)CC3)cc2)c1 | null | 100.5 | null |
910,962 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:23][CH3:24])[C:10](=[O:22])[N:11]([CH3:21])[C:12]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:7]1=[O:25].[H-].[Na+].I[CH3:33]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[CH2:15][C... | CI | COc1c2c(c(NS(C)(=O)=O)n(C)c1=O)CCN(Cc1ccc(F)c(Cl)c1)C2=O | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A cold (0° C.) solution of N-[6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-1-yl]methanesulfonamide (60 mg, 0.14 mmol) in anhydrous DMF (1 mL) was treated with sodium hydride (6.8 mg, 0.17 mmol; 60% dispersion in oil). The resultant mixture was stirred at the same tempe... | COc1c2c(c(N(C)S(C)(=O)=O)n(C)c1=O)CCN(Cc1ccc(F)c(Cl)c1)C2=O | null | null | null |
1,031,420 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=O)=[CH:5][CH:4]=1.[NH2:13][C@H:14](CO)[CH:15]([CH3:17])[CH3:16]>ClC1C=CC=CC=1>[CH:15]([C@H:14]1[CH2:10][O:9][C:7]([C:6]2[CH:11]=[CH:12][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[N:13]1)([CH3:17])[CH3:16] | CC(C)[C@H](N)CO | COC(=O)c1ccc(CO)cc1 | null | null | null | null | 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 | null | null | Under an argon atmosphere, a mixture of methyl 4-hydroxymethylbenzoate (1.5 mmol), (L)-valinol (1.8 mmol), Zn4(OCOCF3)6O (0.15 mmol) and chlorobenzene (2.5 mL) was heated under reflux for 12 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel col... | CC(C)[C@H]1COC(c2ccc(CO)cc2)=N1 | null | 66 | null |
7,774 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [CH3:1][O:2][CH:3]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1Br.[CH2:20]([N:27]1[CH2:32][CH2:31]C(=O)[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCCCC>[CH2:20]([N:27]1[CH2:32][CH2:31][C:1]2([C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:10][CH... | O=C1CCN(Cc2ccccc2)CC1 | COc1ccc(C(OC)c2ccc(F)cc2)c(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCCC | null | null | null | null | null | null | null | null | null | null | null | null | By following the manipulative procedure described above in Example 45, 2-bromo-4'-fluoro-4-methoxybenzhydryl methyl ether and 1-benzyl-4-piperidone are reacted to produce a white solid, m.p. 86°-88°, form heptane. | COc1ccc2c(c1)C1(CCN(Cc3ccccc3)CC1)OC2c1ccc(F)cc1 | null | null | null |
1,190,271 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:32][CH2:33][CH2:34][OH:35])=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[S:36](Cl)([C:39]1[CH:45]=[CH:44][C:42]([CH3:43])=[CH:41][CH:40]... | COC(=O)c1nc(N2CCc3cccc(C(=O)Nc4nc5ccccc5s4)c3C2)sc1CCCO | Cc1ccc(S(=O)(=O)Cl)cc1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate (0.5 g, 0.96 mmol) in DCM (10 mL) was added TsCl (182 mg, 1 mmol), TEA (97 mg, 1 mmol), and catalytic amount of DMAP. The mixture was stirred at rt for 4 hours. The mixture was diluted... | COC(=O)c1nc(N2CCc3cccc(C(=O)Nc4nc5ccccc5s4)c3C2)sc1CCCOS(=O)(=O)c1ccc(C)cc1 | null | null | null |
176,398 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C:12]1([C:15]([OH:17])=O)[CH2:14][CH2:13]1)=[O:11])[CH3:8]>C1C=CC=CC=1.CN(C)C=O>[CH2:7]([O:9][C:10]([C:12]1([C:15]([Cl:4])=[O:17])[CH2:14][CH2:13]1)=[O:11])[CH3:8] | O=C(Cl)C(=O)Cl | CCOC(=O)C1(C(=O)O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | Oxalyl chloride (6.0 g. 47 mmol) was added to a stirred mixture of 1-ethoxycarbonylcyclopropane carboxylic acid (1a) (6 g, 38 mmol) in benzene (25 ml) plus two drops of dimethylformamide. After the gas evolution ceased, the stirring was continued at room temperature for another hour. The reaction mixture was concentrat... | CCOC(=O)C1(C(=O)Cl)CC1 | null | null | null |
160,703 | ord_dataset-e402405fd21e4770a14f157cb62ca439 | null | 1987-01-01T00:07:00 | true | [CH2:1]=[O:2].[N+:3]([C:6]1[N:10]([CH3:11])[C:9]([CH3:12])=[N:8][C:7]=1[CH3:13])([O-:5])=[O:4].[OH-].[NH4+]>CS(C)=O.O>[CH3:11][N:10]1[C:6]([N+:3]([O-:5])=[O:4])=[C:7]([CH3:13])[N:8]=[C:9]1[CH2:12][CH2:1][OH:2] | Cc1nc(C)n(C)c1[N+](=O)[O-] | C=O | null | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 140 | null | Paraformaldehyde (4.05 g, 0.135 mole) and 5-nitro-1,2,4-trimethylimidazole (4.2 g, 0.027 mole) were combined in 25 ml of DMSO and heated at 140° C. for 48 hours (24 hours are found to be optimum), in a 300 ml glass-lined bomb. The reaction mixture was then evaporated in vacuo at 80° C. to give a dark brown oil. This wa... | Cc1nc(CCO)n(C)c1[N+](=O)[O-] | null | 74.8 | null |
1,748,393 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [C:1]([O-:4])(=[S:3])[CH3:2].[K+].CS(O[CH2:11][C@@H:12]([NH:17][C:18]1[C:23]([F:24])=[CH:22][N:21]=[C:20]([Cl:25])[N:19]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])(=O)=O.O>CN(C=O)C>[C:1](=[O:4])([S:3][CH2:11][C@@H:12]([NH:17][C:18]1[C:23]([F:24])=[CH:22][N:21]=[C:20]([Cl:25])[N:19]=1)[C:13]([CH3:16])([CH3:14])[CH3:15])[CH3:... | CC([O-])=S | CC(C)(C)[C@@H](COS(C)(=O)=O)Nc1nc(Cl)ncc1F | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 78 | 1 | Potassium thioacetate (1.30 g, 11.51 mmol) was added to a stirring solution of (S)-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutyl methanesulfonate, 75a, (2.50 g, 7.67 mmol) in dry DMF (50 mL). The resulting brown solution was heated with stirring at 78° C. for 1 hour. The brown suspension was poured into wa... | CC(=O)SC[C@@H](Nc1nc(Cl)ncc1F)C(C)(C)C | null | null | null |
277,246 | ord_dataset-ad17798fcea64e26ba91604fca520090 | null | 1993-01-01T00:10:00 | true | [CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][... | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | N=C(OCC=Cc1ccc(F)cc1)C(Cl)(Cl)Cl | null | O=S(=O)(O)C(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 | 25 | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (200 mg in 6 ml 33% methylene chloride in cyclohexane), p-fluorocinnamyl trichloroacetimidate (112 μl neat) w... | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OCC=Cc4ccc(F)cc4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | null |
241,388 | ord_dataset-685186618e9f4e7aaa72ac40c16ef354 | null | 1992-01-01T00:01:00 | true | C(Br)C=C.[C:5]([O-:8])([O-])=O.[K+].[K+].[CH2:11]([O:14][C:15]1[CH:22]=[CH:21][C:18](C=C)=[CH:17][CH:16]=1)[CH:12]=[CH2:13]>CC(C)=O>[CH2:11]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:5]=[O:8])=[CH:17][CH:16]=1)[CH:12]=[CH2:13] | O=C([O-])[O-] | C=CCOc1ccc(C=C)cc1 | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C=CCBr | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 4-allyloxybenzaldehyde was prepared by reaction of allyl bromide on 4-hydroxybenzaldehyde in refluxing acetone in the presence of K2CO3. The distilled product was used as a precursor for 4-allyloxystyrene synthesis. | C=CCOc1ccc(C=O)cc1 | null | null | null |
1,378,069 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:7]=1.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:24].[Mg+2]>CC(O)C>[Br:1][C:2]1[CH:3]=[N+:4]([O-:24])[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)[CH:7]=1 | O=C([O-])c1ccccc1C(=O)O[O-] | Cn1cc(-c2cncc(Br)c2)cn1 | null | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | null | null | A slurry of 266 mg (1.12 mmol) 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)-pyridine and 1.30 g (2.23 mmol) magnesium monoperoxyphthalate hexahydrate (85%) in 5 ml 2-propanol was stirred for 18 hours at room temperature. The reaction mixture was evaporated and the residue partitioned between saturated sodium bicarbonate soluti... | Cn1cc(-c2cc(Br)c[n+]([O-])c2)cn1 | null | null | null |
1,663,464 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [OH-].[Na+].[C:3]([O:7][C@@H:8]([C:15]1[C:16]([CH3:44])=[N:17][C:18]([CH3:43])=[C:19]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:29][CH:28]=2)[C:20]=1[N:21]1[CH2:24][C:23]([F:26])([F:25])[CH2:22]1)[C:9]([O:11]C(C)C)=[O:10])([CH3:6])([CH3:5])[CH3:4].Cl>C... | Cc1nc(C)c([C@H](OC(C)(C)C)C(=O)OC(C)C)c(N2CC(F)(F)C2)c1-c1ccc(OCCc2ccc(F)cc2)cc1 | null | null | Cl | [Na+] | [OH-] | 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 | 90 | 18 | The 0.40 mL of 1M sodium hydroxide (14.78 mg, 0.37 mmol) was added to a solution (S)-isopropyl 2-(tert-butoxy)-2-(4-(3,3-difluoroazetidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (54 mg, 0.09 mmol) in ethanol (2 mL) and stirred for 18 h at 90° C. The reaction mixture was neutralized with ... | Cc1nc(C)c([C@H](OC(C)(C)C)C(=O)O)c(N2CC(F)(F)C2)c1-c1ccc(OCCc2ccc(F)cc2)cc1 | null | 94.2 | null |
362,729 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [CH3:1][C@:2]([C:14]([NH:16][C@H:17]([CH2:25][OH:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[NH2:3].[C:27]12([CH2:37][C:38](Cl)=[O:39])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2>C1COCC1>[... | O=C(Cl)CC12CC3CC(CC(C3)C1)C2 | C[C@@](N)(Cc1c[nH]c2ccccc12)C(=O)N[C@H](CO)Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of α-methyl-D-tryptophyl-L-phenylalaninol (1 g, 2.85 mmol) and 4-N,N-dimethylaminopyridine (0.35 g, 2.87 mmol ) in dry THF (50 mL ) at 0° C. was treated dropwise, with stirring, with a solution of 1-adamantylacetyl chloride (0.605 g, 2.85 mmol). A precipitate formed immediately. The reaction mixture was left... | CC(Cc1c[nH]c2ccccc12)(NC(=O)CC12CC3CC(CC(C3)C1)C2)C(=O)NC(CO)Cc1ccccc1 | null | 113 | null |
1,257,910 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[N:3]=1.[CH3:11][Mg]Br>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([CH:6]([OH:7])[CH3:11])=[CH:8][CH:9]=1 | C[Mg]Br | Cc1nc(Cl)ccc1C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | null | 6-Chloro-2-methylnicotinaldehyde (300 mg, 1.93 mmol) was taken up in THF (9.6 ml) under argon and cooled to −78° C. Methylmagnesium bromide (1.29 ml, 3.86 mmol) was added dropwise over 5 minutes. The reaction temperature was maintained at −78° C. for 20 minutes, then was allowed to warm to 0° C. over 2 hours. The react... | Cc1nc(Cl)ccc1C(C)O | null | null | null |
1,194,098 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | C[N:2](C)/[CH:3]=[N:4]\[C:5]([C:7]1[N:16]=[C:15]2[N:9]([CH2:10][CH2:11][O:12][C:13]3[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:14]=32)[CH:8]=1)=O.Cl.[CH:24]([NH:27]N)([CH3:26])[CH3:25]>C(O)(=O)C>[Br:21][C:19]1[CH:18]=[CH:17][C:14]2[C:15]3[N:9]([CH:8]=[C:7]([C:5]4[N:27]([CH:24]([CH3:26])[CH3:25])[N:2]=[CH:3][N:4]=4)[N:16]... | CC(C)NN | CN(C)/C=N\C(=O)c1cn2c(n1)-c1ccc(Br)cc1OCC2 | null | Cl | 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 | 100 | null | Alternatively, to a suspension of 8-bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylamino-meth-(Z)-ylideneamide (8.52 g, 23.5 mmol) in acetic acid (50 mL) was added isopropylhydrazine hydrochloride (3.37 g, 30.5 mmol) and the reaction mixture heated at 100° C. for 1 h. The reaction mixtur... | CC(C)n1ncnc1-c1cn2c(n1)-c1ccc(Br)cc1OCC2 | null | 89.6 | null |
611,882 | ord_dataset-5c4ee54447b84205a10f9c0473172972 | null | 2003-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30]CC)=[O:29])=[CH:24][CH:23]=3)=[O:20])=[CH:13]1)[N:8]=[C:7]([C:33]([O:35]CC)=[O:34])[C:6](=[O:38])[NH:5]2.[OH-].[K+]>C(O)C>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:19]([... | CCOC(=O)c1ccc(NC(=O)NCc2ccn(-c3cc4nc(C(=O)OCC)c(=O)[nH]c4cc3Cl)c2)cc1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of the compound (25.4 mg, 47.2 μmol) of Example 6 in ethanol (2 ml) was added 1 mol/L aqueous solution of potassium hydroxide (189 μl, 189 μmol), and the mixture was refluxed for 1.5 hours. After cooling, solvent was distilled off. The residue was dissolved into a small quantity of water, which was brough... | O=C(NCc1ccn(-c2cc3nc(C(=O)O)c(=O)[nH]c3cc2Cl)c1)Nc1ccc(C(=O)O)cc1 | null | null | null |
133,295 | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | null | 1985-01-01T00:08:00 | true | [CH3:1][CH:2]([CH3:4])[O-:3].[Al+3].[CH3:6][CH:7]([CH3:9])[O-].[CH3:10][CH:11]([CH3:13])[O-].[C:14]1([CH3:20])[CH:19]=[CH:18]C=C[CH:15]=1>>[CH3:6][C:7]1([CH3:9])[C:13]2[CH2:11][CH2:10][CH2:4][CH:2]([OH:3])[C:1]=2[C:14]([CH3:15])([CH3:20])[CH:19]1[CH3:18] | CC(C)[O-] | Cc1ccccc1 | null | [Al+3] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 8 | Into a 2-liter reaction vessel are placed 831 ml of toluene and 226.9 grams (1.11 moles) of aluminum isopropoxide. The mixture is heated to reflux and while refluxing, over a one hour period, tetrahydro pentamethylindane epoxide having the structure: ##STR63## is added to the reaction mass. The reaction mass is continu... | CC1C(C)(C)C2=C(C(O)CCC2)C1(C)C | null | null | null |
958,946 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [C:1]([O:5][C:6](=[O:23])[CH2:7][O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:24]1([C:30]2[O:31][C:32]([C:38]([F:41])([F:40])[F:39])=[C:33]([C:35](O)=[O:36])[N:34]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(CC)CC.F[P-](F)(F)(F)... | CC(C)(C)OC(=O)COC1CCN(c2ccc([N+](=O)[O-])cn2)C1 | O=C(O)c1nc(-c2ccccc2)oc1C(F)(F)F | null | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | [1-(5-Nitro-pyridin-2-yl)-pyrrolidin-3-yloxy]-acetic acid tert-butyl ester (280 mg, 0.866 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (245 mg, 0.953 mmol), Et3N (486 uL, 3.46 mmol) and BOP (402 mg. 0.909 mmol). Following work-up as above, the crude material was ... | CC(C)(C)OC(=O)COC1CCN(c2ccc(NC(=O)c3nc(-c4ccccc4)oc3C(F)(F)F)cn2)C1 | null | 36.9 | null |
1,598,974 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[N:13]=[C:14]=[O:15].[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]3[CH:36]=[C:35]([NH:37][CH3:38])[N:34]=[CH:33][N:32]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH3:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8... | CCN1CCN(c2ccc(Nc3cc(NC)ncn3)cc2)CC1 | COc1cc(OC)c(Cl)c(N=C=O)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | 1.5 | The title compound was prepared by adding 2,6-dichloro-3,5-dimethoxyphenyl-isocyanate (1.25 eq.) to a solution of N-[4-(4-ethyl-piperazin-1-yl)-phenyl]-N′-methyl-pyrimidine-4,6-diamine (2.39 g, 7.7 mmol, 1 eq.) in toluene and stirring the reaction mixture for 1.5 h at reflux. Purification of the crude product by silica... | CCN1CCN(c2ccc(Nc3cc(N(C)C(=O)Nc4c(Cl)c(OC)cc(OC)c4Cl)ncn3)cc2)CC1 | null | null | null |
1,266,077 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][Si](Cl)(C)C>CO>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5] | O=C(O)c1cc(F)cc([N+](=O)[O-])c1F | C[Si](C)(C)Cl | 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 | 2,5-Difluoro-3-nitrobenzoic acid (2.00 g, 9.847 mmol) was dissolved in MeOH (60 mL). TMSCl (6.220 mL, 49.24 mmol) was added, and the reaction mixture was stirred at reflux for 4 hours. The reaction mixture was concentrated to about 20 mL, and the crystals produced were filtered and dried under high vacuum providing met... | COC(=O)c1cc(F)cc([N+](=O)[O-])c1F | null | 72.5 | null |
1,536,747 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20](COCC[Si](C)(C)C)[C:19](=[O:29])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[C:31]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1>>[C:31]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:... | CCOC(=O)c1cnn(-c2nc3ccc(I)cc3c(=O)n2COCC[Si](C)(C)C)c1 | OB(O)c1cccc(-c2ccccc2)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 titled compound was prepared in a manner analogous to Example 69, steps C-E using 1-[6-iodo-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (product from Example 69, step B) and biphenyl-3-boronic acid. MS (ESI): mass calcd. for C24H16N4O3, 408.1; m/z... | O=C(O)c1cnn(-c2nc3ccc(-c4cccc(-c5ccccc5)c4)cc3c(=O)[nH]2)c1 | null | null | null |
596,568 | ord_dataset-843ef38b45484f72826f5f39d8a29c4d | null | 2003-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1)=[O:10].[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][CH2:33][CH2:34]I>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:34][CH2... | O=C(Cc1ccccc1Cl)c1ccc(OCCN2CCCCC2)cc1 | ICCOC1CCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2-(2-Chlorophenyl-1-[4-(2-piperidinylethoxy)phenyl]-4-(tetrahydropyranyloxy)butan-1-one is prepared by PTC reaction according to the method described in the example 4d using 2-(2-chlorophenyl)-1-[4-(2-piperidinylethoxy)phenyl]ethanone (1.5 g, 4.2 mmol) and 2-tetrahydropyranyloxy-1-iodoethane (1.3 g, 5.1 mmol) as the st... | O=C(c1ccc(OCCN2CCCCC2)cc1)C(CCOC1CCCCO1)c1ccccc1Cl | null | null | null |
101,833 | ord_dataset-72d9f7ef86df410fac4765c9632d459b | null | 1983-01-01T00:01:00 | true | [C:1]([C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:11]=1[O:24]C)(C)[C:4]([O:6]CC)=[O:5])#N.I.[OH-].[K+].CO>C(O)(=O)C>[OH:24][C:11]1[C:12]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[CH:13][CH:14]=[CH:15][C:10]=1[CH:3]([CH3:1])[C:4]([OH:6])=[... | CCOC(=O)C(C)(C#N)c1cccc(Sc2ccccc2C)c1OC | null | null | I | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CO | null | null | null | null | null | null | null | null | null | null | null | A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolylthio)phenyl]propionate (10 g) and hydriodic acid (58%, 12 ml) in acetic acid (24 ml) was refluxed under heating for 24 hours. After concentration, the residue was dissolved in aqueous sodium hydrogen sulfite and extracted with diethyl ether. The extract was washed with ... | Cc1ccccc1Sc1cccc(C(C)C(=O)O)c1O | null | 47.5 | null |
1,270,187 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([C@H:42]2[CH2:47][CH2:46][C@@H:45]([O:48][CH2:49][CH3:50])[CH2:44][CH2:43]2)=[... | CCOP(=O)(Cc1ccc(Nc2ncc(C(F)(F)F)c(Cl)n2)c(OC)c1)OCC | CCO[C@H]1CC[C@@H](c2ccc(N)c3c2CN(C)C3=O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared according to the procedure for Example 102 using diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate and 7-amino-4-(cis-4-ethoxycyclohexyl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 166A). 1H NMR (DMSO-d6, 400 MHz): δ=1.15-1.22 (m, 9H), 1.44-... | CCOP(=O)(Cc1ccc(Nc2ncc(C(F)(F)F)c(Nc3ccc([C@H]4CC[C@@H](OCC)CC4)c4c3C(=O)N(C)C4)n2)c(OC)c1)OCC | null | null | null |
1,761,793 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[Li]CCCC.[O:14]=[C:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1>O1CCCC1.C(OCC)C.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]2([OH:14])[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:18]2)=[CH:4][CH:3]=1 | Brc1ccc(I)cc1 | CC(C)(C)OC(=O)N1CC(=O)C1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -78 | 1.5 | Into a 1-L 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1-bromo-4-iodobenzene (25.0 g, 88.4 mmol) in tetrahydrofuran/diethyl ether (400/200 mL). The solution was cooled to −78° C. then n-BuLi (2.5 M, 37.1 mL, 92.8 mmol) was added drop-wise over 10 min... | CC(C)(C)OC(=O)N1CC(O)(c2ccc(Br)cc2)C1 | null | 27.6 | null |
1,454,355 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([O:5][C:6](=[O:30])[C@@H:7]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:8][CH2:9][CH2:10][NH:11][CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[C:31]([O:35][C:36]([N:38]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[C:39]1[CH2... | CC(C)(C)OC(=O)n1c(CCl)nc2ccccc21 | CC(C)(C)OC(=O)N[C@@H](CCCNC1CCCc2cccnc21)C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | Using the General Procedure for N-alkylation: A solution of (2S)-2-(tert-butoxycarbonylamino)-5-(5,6,7,8-tetrahydroquinolin-8-ylamino)-pentanoic acid tert-butyl ester (0.700 g, 1.67 mmol), 1-(tert-butoxycarbonyl)-2-(chloromethyl)-benzimidazole (0.690 g, 2.59 mmol) and N,N-diisopropylethylamine (0.60 mL, 3.44 mmol) in C... | CC(C)(C)OC(=O)NC(CCCN(Cc1nc2ccccc2n1C(=O)OC(C)(C)C)C1CCCc2cccnc21)C(=O)OC(C)(C)C | null | 76.5 | null |
1,334,440 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[OH:13])[CH3:2].[H-].[Na+].Br[CH2:17][C:18]#[N:19]>CN(C=O)C>[CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[O:13][CH2:17][C:18]#[N:19])[CH3:2] | CCc1c(O)cc(C)c2sccc12 | N#CCBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 4-Ethyl-7-methyl-benzo[b]thiophen-5-ol (438 mg, 2 mmol) was dissolved in 10 ml DMF, and the reaction mixture was cooled to zero degrees C. Sodium hydride (66 mg, 3 mmol) was added and the reaction mixture was stirred 30 minutes at zero C. Bromoacetonitrile (170 ul, 3 mmol) was added, and the reaction mixture was stirre... | CCc1c(OCC#N)cc(C)c2sccc12 | null | 91.2 | null |
1,407,001 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [Br:1][C:2]1[O:6][C:5]([CH2:7]O)=[CH:4][CH:3]=1.[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(Cl)(Cl)[Cl:29]>>[Br:1][C:2]1[O:6][C:5]([CH2:7][Cl:29])=[CH:4][CH:3]=1.[C:22]1([P:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:... | OCc1ccc(Br)o1 | ClC(Cl)(Cl)Cl | null | c1ccc(P(c2ccccc2)c2ccccc2)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 | 75 | null | To a solution of (5-bromo-2-furanyl)methanol (Example 310A) (144 mmol) in dry carbon tetrachloride (30 mL) was added triphenylphosphine (6.0 g, 228 mmol) at rt. The reaction is heated at 75° C. for 1 h. Concentration and purification by radial chromatography (0-10% EtOAc-hexanes gradient) afforded the title compound wi... | ClCc1ccc(Br)o1 | null | null | null |
186,563 | ord_dataset-754e10d30fb249229e130865010ab25b | null | 1989-01-01T00:03:00 | true | [CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH2:3]1 | CC1=CC[C@@H](C(C)(C)O)CC1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | α-Terpineol (6.17 g) in ethanol (130 ml) was hydrogenated for 1 h at atmospheric pressure using 10% Pd-C catalyst (290 mg). The catalyst was then removed by filtration through Kieselguhr and the solvent was removed under reduced pressure to leave the title compound as an oil (5.93 g). Distillation gave an oil (4.56 g) ... | CC1CCC(C(C)(C)O)CC1 | null | 94.9 | null |
1,616,146 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH2:1][C:2]1[C:7]([N:8]([C:10]([O:12][CH3:13])=[O:11])[NH2:9])=[C:6]([NH2:14])[N:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:16]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[C:41](N1C=CN=C1)(N1C=CN=C1)=[O:42]>CN(C)C=O>[NH2:1][C:2]1[C:7]2[N:8]([C:1... | COC(=O)N(N)c1c(N)nc(-c2nn(Cc3ccccc3F)c3ncccc23)nc1N | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 60 | 5 | 56 mg (0.132 mmol) of the compound obtained in example 56A were initially charged in 3 ml of dimethylformamide, and 27.6 μl (0.159 mmol) of N,N-diisopropylethylamine and 25.7 mg (0.159 mmol) of carbonyldiimidazole were added. After 5 h at RT, another 27.6 μl (0.159 mmol) of N,N-diisopropylethylamine and 25.7 mg (0.159 ... | COC(=O)N1NC(=O)Nc2nc(-c3nn(Cc4ccccc4F)c4ncccc34)nc(N)c21 | null | 42.1 | null |
802,729 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | C([O:3][P:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][P:4]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)([O:5][CH2:6][CH3:7])=[O:3])[CH3:10] | O=C(O)c1ccc(CBr)cc1 | CCOP(OCC)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | 12 | Triethylphosphite (9.28 mL, 53.3 mmol) and α-bromo-p-toluic acid (10.4 g, 48.4 mmol) were suspended in toluene (25 mL) and the mixture was heated to reflux for 18 h. The mixture was cooled to room temperature. After 12 h, the resulting white solid was collected by suction filtration, washed with petroleum ether and dri... | CCOP(=O)(Cc1ccc(C(=O)O)cc1)OCC | null | 77.4 | null |
728,071 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | [CH3:1][CH:2]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1)[C:3](O)=[O:4].Cl.[O:21]=[C:22]1[CH2:27][CH2:26][C:25]([NH2:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1>>[CH3:1][CH:2]([C:6]1[CH:7]=[C:8]([C:16]([F:17])([F:19])[F:18])[CH:9]=[C:10... | NC1(c2ccccc2)CCC(=O)CC1 | CC(C(=O)O)c1cc(C(F)(F)F)cc(C(F)(F)F)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 | Prepared from (RS)-α-methyl-3,5-bis(trifluoromethyl)benzeneacetic acid (Description 4) and 4-oxo-1-phenylcyclohexylamine hydrochloride (Description 18) according to the method of Example 1. 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, s), 7.72 (2H, s), 7.29 (5H, m), 5.71 (1H, s), 3.70 (1H, q, J 7.0 Hz), 2.81 (1H, m), 2.64 (1H, ... | CC(C(=O)NC1(c2ccccc2)CCC(=O)CC1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null |
729,790 | ord_dataset-eb4226b4f7644a01a737e7547b70014a | null | 2006-01-01T00:09:00 | true | C[Mg]Br.C([O:6][CH2:7][CH3:8])C.CON(C)C([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1)=O>C1COCC1>[CH3:21][S:20][C:16]1[N:17]=[C:18]([C:7](=[O:6])[CH3:8])[CH:19]=[CH:14][N:15]=1 | CON(C)C(=O)c1ccnc(SC)n1 | CCOCC | null | C[Mg]Br | 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 | 0 | 0.5 | A solution of methylmagnesium bromide in diethyl ether (3.0 M, 6.10 mL, 18.3 mmol, 3.0 equiv) was added to a solution of N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (1-2, 1.30 g, 6.10 mmol, 1 equiv) in THF at −78° C. The reaction mixture was warmed to 0° C., stirred for 30 minutes, then partitioned betwee... | CSc1nccc(C(C)=O)n1 | null | null | null |
1,710,097 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[S:41][C:22]3=[N:23][C:24]([N:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)=[CH:25][C:26](=[O:27])[N:21]3[N:20]=2)[CH:16]=[N:17][CH:18]=1)=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15... | CC(C)(C)OC(=O)NCC(=O)Nc1cncc(-c2nn3c(=O)cc(N4CCN(C(=O)OC(C)(C)C)CC4)nc3s2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of tert-butyl 4-(2-(5-(2-(tert-butoxycarbonylamino)acetamido)pyridin-3-yl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (20 mg, 0.034 mmol) in DCM (2 ml) is added TFA (0.5 ml). The mixture is stirred for 2 h, concentrated in vacuo and the residue is directly purified by prepar... | NCC(=O)Nc1cncc(-c2nn3c(=O)cc(N4CCNCC4)nc3s2)c1 | null | null | null |
1,691,819 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)N)=[CH:5][CH:4]=1.C(O[CH:23](OCC)[CH2:24][CH2:25][CH2:26][NH:27][CH3:28])C>C(O)C.O>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:9]([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C... | NN(CCCc1ccccc1)c1ccc(Cl)cc1 | CCOC(CCCNC)OCC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 90 | null | 28% aqueous HCl (0.07 mL, 0.54 mmol) was added to a solution of N-(4-Chloro-phenyl)-N-(3-phenyl-propyl)-hydrazine (261 mg, 1 mmol) in ethanol (1 mL) and water (0.5 mL) under a nitrogen atmosphere. The reaction was heated to 60° C. (oil bath temperature) and 4,4-diethoxy-N-methylbutan-1-amine (175 mg, 1 mmol) was added.... | CNCCc1cn(CCCc2ccccc2)c2ccc(Cl)cc12 | null | 74.3 | null |
807,992 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | C[Si](C)(C)CC[O:5][C:6](=[O:21])[CH2:7][CH2:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:10].Cl[C:25]1[N:30]=[C:29]([O:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[N:28]=[C:27]([N:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][CH2:39][CH2:38]2)[N:26]=1>>[Cl:20... | Clc1nc(OC2CCCC2)nc(N2CCCc3ccccc32)n1 | C[Si](C)(C)CCOC(=O)CCC(=O)c1c[nH]c2ccc(Cl)cc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Arylation of 4-(5-chloro-1H-indol-3-yl)-4-oxo-butyric acid 2-trimethylsilanyl-ethyl ester with 1-(4-chloro-6-cyclopentyloxy-[1,3,5]-triazin-2-yl)-1,2,3,4-tetrahydro-quinoline and subsequent hydrolysis as outlined previously yielded the titled compound. Rf 0.30 (5% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz)... | O=C(O)CCC(=O)c1cn(-c2nc(OC3CCCC3)nc(N3CCCc4ccccc43)n2)c2ccc(Cl)cc12 | null | null | null |
188,975 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:26](O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C1(C)C=CC=CC=1.O>[CH2:39]([O:12][C:11](=[O:13])[C@H:2]([CH2:3][C:4]1[CH:5]=[CH:6]... | N[C@@H](Cc1ccc(O)cc1)C(=O)O | CCCCCCCCCCCCCCO | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 11 | 9.1 g (0.05 mole) of L-tyrosine was used, 11.4 g (0.06 mole) of p-toluenesulfonic acid hydrate was used, and 11.79 g (0.055 mole) of myristyl alcohol was used as an alcohol. After 200 ml of toluene was added thereto as a solvent, these materials were stirred and mixed well. The resulting reaction mixture was heated at ... | CCCCCCCCCCCCCCOC(=O)[C@@H](N)Cc1ccc(O)cc1 | null | 80 | null |
850,903 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [CH:1]([Mg]Br)=[CH2:2].[Cl:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]>C1COCC1>[Cl:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])[CH:1]=[CH2:2] | C=C[Mg]Br | O=C(CCCl)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 1.5 | Anhydrous CeCl3 (16 g, 64.9 mmol) was stirred vigorously in 100 mL THF for 2 h 15 min. The suspension was then cooled to −78° C. and a 1 M solution of vinylmagnesiumbromide (62 mL, 62.3 mmol) was added. After 1.5 h at −78° C., a solution of 3-chloropropiophenone (7 g, 14.5 mmol) in 20 mL THF was added dropwise via cann... | C=CC(O)(CCCl)c1ccccc1 | null | 270 | null |
983,111 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1.I[C:30]1[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2... | Cn1cc(I)cn1 | C#Cc1ccc(Cc2cc([C@@]3(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)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 compound was obtained starting from 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene and 4-iodo-1-methyl-1H-pyrazole. | Cn1cc(C#Cc2ccc(Cc3cc([C@@]4(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)ccc3Cl)cc2)cn1 | null | null | null |
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