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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
618,895 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [H-].[Na+].[N:3]1([CH2:16][CH2:17][OH:18])[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:18][CH2:17][CH2:16][N:3]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1)[C:20... | OCCn1cnc2cnc3ccccc3c21 | BrCc1ccccc1 | 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 | null | 1.5 | Under a nitrogen atmosphere, sodium hydride (16.88 g of 60% in mineral oil, 422 mmol) was added in portions to a solution of 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethanol (60.0 g, 281 mmol) in anhydrous N,N-dimethylformamide (600 mL). The alkoxide was allowed to stir for about 1.5 hours. Benzyl bromide (50.2 mL, 422 mmol) ... | c1ccc(COCCn2cnc3cnc4ccccc4c32)cc1 | null | null | null |
752,986 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [NH2:1][C:2]1[C:3]([NH:23][CH3:24])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:25][C:26]1[C:27]([O:42][CH3:43])=[N:28][C:29]([O:40][CH3:41])=[C:30]([Cl:39])[C:31]=1[C:32](=O)[C:33]([O:35]CC)=O.CC(O)=O>COCCO>[Cl:39][C:3... | CCN(CC)CCOc1ccc(Nc2ncc(N)c(NC)n2)cc1 | CCOC(=O)C(=O)c1c(Cl)c(OC)nc(OC)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 0.66 g (2 mmol) of 5-amino-2-[[4-[2-(diethylamino)-ethoxy]phenyl]amino]-4-(methylamino)pyrimidine, 1.23 g (4 mmol) of ethyl 2-(3,5-dichloro-2,6-dimethoxypyridin-4-yl)-2-oxoacetate, and 1 mL of HOAc in 20 mL of 2-methoxyethanol is heated under reflux for 16 hours. Workup as in 6 above gives 0.59 g (51%) of ... | CCN(CC)CCOc1ccc(Nc2ncc3nc(-c4c(Cl)c(OC)nc(OC)c4Cl)c(=O)n(C)c3n2)cc1 | null | 51.4 | null |
374,410 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:23]([C:24](O)=[O:25])[C:22]=1[C:30](O)=[O:31].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]... | O=C(O)c1cccc(F)c1C(=O)O | NCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | 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 | 18 | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.37 gm, 8.98 mmoles), 3-fluorophthalic acid (1.82 gm, 9.9 moles) and dicyclohexylcarbodiimide (DCC, 5.5 gm, 26.7 mmoles, 2.6 eq) in dichloromethane (DCM, 250 ml) was stirred at room temperature for 18 hrs. The solids were filtered off. The or... | O=C1c2cccc(F)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | null |
852,342 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [CH2:1]([O:8][C:9](=[O:35])[CH:10]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:37].[K+]>C1COCC1.O>[CH2:1]([O:8][C:9... | O=[Mn](=O)(=O)[O-] | CC(C)(C)OC(=O)NC(Cc1ccc(Oc2ccc(C=O)cc2)cc1)C(=O)OCc1ccccc1 | null | [K+] | null | 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 | 70 | null | Benzyl ester 3 (4.6 g, 9.7 mmol) was dissolved in THF (100 mL) and the solution stirred at 70° C. Potassium permanganate (7.7 g, 48.5 mmol) dissolved in water (125 mL) was added slowly through a dropping funnel over a period of 2 hours. After addition was complete, reaction mixture was stirred at 70° C. for 30 min and ... | CC(C)(C)OC(=O)NC(Cc1ccc(Oc2ccc(C(=O)O)cc2)cc1)C(=O)OCc1ccccc1 | null | 94.4 | null |
702,833 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[C:8]1([C:14]2[O:18][N:17]=[CH:16][C:15]=2[CH2:19][CH2:20][C:21](O)=[O:22])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[N:3]1[CH:4]=[CH:5][N:6]=[CH:7][C:2]=1[NH:1][C:21](=[O:22])[CH2:20][CH2:19][C:15]1[CH:16]=[N:17][O:18][C:14... | O=C(O)CCc1cnoc1-c1ccccc1 | Nc1cnccn1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | A mixture of 2-aminopyrazine (0.26 g), 3-(5-phenyl-4-isoxazolyl)propionic acid (0.58 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.46 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.60 g) and N,N-dimethylformamide (15 ml) was stirred at room temperature overnight. The reaction mixture was poured in... | O=C(CCc1cnoc1-c1ccccc1)Nc1cnccn1 | null | 58.5 | null |
952,205 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [CH2:1]([CH2:3][NH2:4])[OH:2].C(N(CC)CC)C.Cl.[CH:13]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([S:26]([C:29]([CH3:34])([CH3:33])[C:30](Cl)=[O:31])(=[O:28])=[O:27])=[CH:25][C:20]=3[N:19]=[C:18]2[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:15][CH2:14]1>ClCCl>[CH:13]1([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][C:24]([S:2... | CC(C)(C)Cc1nc2cc(S(=O)(=O)C(C)(C)C(=O)Cl)ccc2n1CC1CC1 | NCCO | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | To a mixture of ethanolamine (54 mg, 0.886 mmol), triethylamine (0.184 mL, 1.32 mmol) and dichloromethane (3 mL) was added a solution of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoyl chloride hydrochloride (Step A of Example 7, 198 mg, 0.443 mmol) in dichloromethane (... | CC(C)(C)Cc1nc2cc(S(=O)(=O)C(C)(C)C(=O)NCCO)ccc2n1CC1CC1 | null | 54.4 | null |
1,562,455 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N=C2CCCCC2=O)=[C:4]([F:17])[CH:3]=1.OS(O)(=O)=O.[C:23]([O-:26])(O)=O.[Na+]>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([F:17])[CH:3]=1)[NH:8][C:7]1[C:23](=[O:26])[CH2:5][CH2:4][CH2:3][C:2]2=1 | O=C([O-])O | O=C1CCCCC1=NNc1ccc(Cl)cc1F | null | O=S(=O)(O)O | [Na+] | 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 | 80 | null | To a solution of 2-(2-(4-chloro-2-fluorophenyl)hydrazono)cyclohexanone (0.5 g, 1.9 mmol) in MeCN (5 mL), H2SO4 (0.31 mL, 5.9 mmol, 1.8M solution) was added slowly and the resulting mixture was heated to 80° C. for 12 h. The reaction mixture was cooled to room temperature, basified with saturated NaHCO3 (pH-8) and extra... | O=C1CCCc2c1[nH]c1c(F)cc(Cl)cc21 | null | 25 | null |
214,170 | ord_dataset-b67d30cd146f49dcbf24faee022f1a09 | null | 1990-01-01T00:08:00 | true | [OH:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[CH2:29]([O:28][C:26]([CH2:25][O:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])=[C... | CCOC(=O)CBr | O=C(NCc1ccccn1)c1cc(OCC(F)(F)F)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using the general method of Example I Part A, 9.8 g (0.03 mole) of 2-hydroxy-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide was reacted with 7.0 g (0.042 mole) of ethyl bromoacetate to give 7.6 g of ivory powdery -(ethoxycarbonylmethoxy)-N-(2-pyridylmethyl)-5-(2,2,2-trifluoroethoxy)benzamide, m.p. 109°-111° C. | CCOC(=O)COc1ccc(OCC(F)(F)F)cc1C(=O)NCc1ccccn1 | null | null | null |
462,725 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | C([O:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=O)C.NC1C=C(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=[O:27])C=2C=1>O>[OH:4][C:5]1[C:6]([CH3:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:9])=[O:27] | CC(=O)Oc1cccc(C(=O)Cl)c1C | Nc1cc(S(=O)(=O)O)c2cccc(S(=O)(=O)O)c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | null | The present invention relates to a process for the preparation of 3-acetoxy-2-methylbenzoyl chloride by reacting an alkali metal salt of 3-aminonaph-thalene-1,5-disulfonic acid with alkali metal hydroxide and water in the weight ratio 1:(1 to 1.6):(1 to 1.6) at 220 to 320° C. to give the dialkali metal salt of the 3-hy... | Cc1c(O)cccc1C(=O)O | null | null | null |
94,142 | ord_dataset-62e11cab5a6e47d89878616c244e20ef | null | 1982-01-01T00:05:00 | true | [CH2:1]=[C:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][C:6](=[O:14])[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[H][H]>[Pd].C(O)C>[CH3:1][CH:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][C:6](=[O:14])[CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2 | [H][H] | C=C1c2ccccc2CC(=O)Cc2ccccc21 | 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 | 31.4 g. (0.134 mole) of 12-methylene-5,6,7,12-tetrahydrodibenzo[a,d]cycloocten-6-one and 270 mg. of 10% palladium on charcoal were combined in 225 ml. of 95% ethanol and shaken under 50 p.s.i.g. of hydrogen. When hydrogen uptake ceased at about 1 mole equivalent, the mixture was filtered and evaporated in vacuo to give... | CC1c2ccccc2CC(=O)Cc2ccccc21 | null | null | null |
1,397,514 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH:18][C:19]2[N:27]=[CH:26][N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][NH:23]3)[CH3:17])[CH2:3][CH2:2]1.[O:28]1[CH2:31][C:30](=O)[CH2:29]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:28]1[CH2:31][CH:30]([N:1]2[CH2:... | O=C1COC1 | C[C@H](Nc1ncnc2[nH]cnc12)c1nc2ccccc2n1C1CCNCC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCCl | null | null | null | null | null | null | null | null | null | null | 4 | To a mixture of (S)—N-(1-(1-(piperidin-4-yl)-1H-benzo[d]imidazol-2-yl)ethyl)-9H-purin-6-amine from Example 113 (99 mg, 0.273 mmol) in anhydrous DCE (10 mL) was added oxetan-3-one (32 μL, 0.546 mmol) followed by AcOH (16 μL, 0.273 mmol) and 4 Å (angstrom) powdered molecular sieves (0.1 g). After stirring for 4 h, sodium... | C[C@H](Nc1ncnc2[nH]cnc12)c1nc2ccccc2n1C1CCN(C2COC2)CC1 | null | null | null |
1,191,988 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | [OH-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1>CO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[N:13][CH:14]=1)([O-:20])=[O:19] | Nc1ccc(O)cc1 | O=[N+]([O-])c1ccc(Cl)nc1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 70 | 1.5 | To a solution of sodium hydroxide (730 mg, 18.25 mmol) in methanol was added 4-aminophenol (2.00 g, 18.32 mmol). After the resulting mixture was made to dissolve, methanol was evaporated under reduced pressure. To the residue was added DMF (20 mL), and then 2-chloro-5-nitropyridine (2.91 g, 18.35 mmol). The reaction so... | Nc1ccc(Oc2ccc([N+](=O)[O-])cn2)cc1 | null | null | null |
512,846 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | C(=O)([O-])[O-].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[N:10]=[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]=2[C:23]2[O:27][CH:26]=[N:25][CH:24]=2)[N:8]=1.Cl[N:29]1[N:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[NH:30]1>CN(C=O)C>[CH3:14][O:13][C:11]1[CH:12]=[C:7]([O:6][CH3:5])[N:8]... | COC1=CC(OC)=NN(Cl)N1 | COc1cc(OC)nc(Oc2cccc(O)c2-c2cnco2)n1 | null | O=C([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | To DMF solution containing 0.14 g pottasium carbonate and 0.15 g 5-[2-(4,6-dimethoxypyrimidine-2-yloxy)-6-hydroxyphenyl]oxazole, was added at once DMF solution containing 0.13 g 2-chloro-4,6-dimethoxytriazine. The solution reacted was stirred for a night at room temperature. After completing the reaction, the solution ... | COC1=CC(OC)=NN(Oc2cccc(Oc3nc(OC)cc(OC)n3)c2-c2cnco2)N1 | null | null | null |
853,949 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>>[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)=[O:16] | O=C(Cl)CCCCCl | c1ccc2c(c1)CCO2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 2,3-dihydro-1-benzofuran (24.5 g) and 5-chlorovaleryl chloride (34.8 g) according to the same method as that of Reference Example 1, the title compound was obtained as colorless crystals (32.4 g) having a melting point of 56 to 57° C. | O=C(CCCCCl)c1ccc2c(c1)CCO2 | null | null | null |
1,030,369 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]3[N:27]4[CH2:28][CH2:29][NH:30][CH2:31][C:26]4=[N:25][C:19]=3[C:20]([NH2:24])=[N:21]2)=[CH:16][CH:15]=1>CN(C=O)C>[Br:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]3[N:27]4[CH2:28][CH2:29][N:30]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:31][C:26]4=... | CS(=O)(=O)Cl | Nc1nc2cc(Br)ccc2c2c1nc1n2CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 8 | Triethylamine (3.82 g, 37.7 mmol) and methanesulfonyl chloride (2.38 g, 20.7 mmol) were sequentially added to a solution of 3-bromo-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (6.00 g, 18.9 mmol) in DMF (50 mL), and the mixture was stirred at ambient temperature overnight. A precipitate formed... | CS(=O)(=O)N1CCn2c(nc3c(N)nc4cc(Br)ccc4c32)C1 | null | 8 | null |
543,474 | ord_dataset-49124ff635234889bd8dcfe87f4f9013 | null | 2002-01-01T00:04:00 | true | Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.B1([C:22]2[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=2)OCCCO1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=... | CN(C)CCn1ccc2ccc(Br)cc21 | c1cncc(B2OCCCO2)c1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Na+] | 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 | In a 25 mL round bottom flask equipped with a stir bar was added 6-Bromo-1-(2-(N,N-dimethylamino)ethyl)-1H-indole (0.10 g; 0.37 mmol), pyridine-3-boronic acid-1,3-propanediol cyclic ester (0.12 g; 0.74 mmol), toluene (10 mL), sodium carbonate (2M) (4 mL) and tetrakis(triphenylphosphine)palladium(0) (0.02 g; 0.04 mmol).... | CN(C)CCn1ccc2ccc(-c3cccnc3)cc21 | null | 81.5 | null |
427,423 | ord_dataset-8cce6f317d644b348a7978a2dce3ea01 | null | 1999-01-01T00:03:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:9])[C:7]=1[CH3:8])[NH2:10] | Cc1c(F)cc([N+](=O)[O-])cc1Br | 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 | 25 | 16 | To 3-bromo-5-fluoro-4-methylnitrobenzene (1.4 gm, 6.0 mmol) in ethanol (100%, 25 mL) was added (c) HCl (7.0 mL) and stannous chloride dihydrate (4.1 gm, 18 mmol). The solution was stirred at room temperature for 16 hr and then concentrated in vacuo. The residue was diluted with water, made basic with 2N NaOH and extrac... | Cc1c(F)cc(N)cc1Br | null | 106.2 | null |
1,282,355 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15](=[O:17])[N:14]([CH3:18])[C:13]=2[CH:19]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15](=[O:17])[N:14]([CH3:18])[C:13]=2[CH:19]=1 | Cn1c(=O)oc2ccc(O[Si](C)(C)C(C)(C)C)cc21 | null | null | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 16 | To a cooled (0° C.) solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-1,3-benzoxazol-2(3H)-one (1.20 g, 4.3 mmol) in anhydrous tetrahydrofuran (15 mL) was added dropwise tetra-n-butylammonium fluoride (4.7 mL, 1 M in tetrahydrofuran, 4.7 mmol). The reaction mixture was stirred at ambient temperature for 16 h and ... | Cn1c(=O)oc2ccc(O)cc21 | null | 66.2 | null |
525,658 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | C[O-].[Na+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:26](OCC)=O)=[N:12]2)=[CH:7][C:6]=1[CH3:31].C([NH2:34])=O>>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])... | CCOC(=O)c1cc(-c2ccc(S(C)(=O)=O)cc2)n(-c2ccc(F)c(C)c2)n1 | NC=O | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 110 | 2 | A mixture of sodium methoxide (169 mg) and ethyl 1-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxylate (420 mg) in formamide (5 ml) was warmed at 110° C. for 30 minutes. The reaction mixture was poured into ice-water (50 ml) and the precipitate was collected by filtration, and washed with water... | Cc1cc(-n2nc(C#N)cc2-c2ccc(S(C)(=O)=O)cc2)ccc1F | null | null | null |
376,981 | ord_dataset-846d411edee44814931e062174d7ef12 | null | 1997-01-01T00:09:00 | true | [CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:11]=2)[CH2:8][NH:7][CH2:6]1)=[O:4].Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[CH3:33][O:32][C:30]([N:7]1[CH2:8][C@@H:9]([C:10]2[... | COC(=O)C1CNCC1c1ccc(OC)c(OCCCOc2ccccc2)c1 | COC(=O)Cl | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | ClCCl | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 3-methoxycarbonyl-4-[3-(3-phenoxypropoxy)-4-methoxyphenyl]pyrrolidine (720 mg, 1.87 mmol) in 5 mL of CH2Cl2 at 0° C. was added DMAP (275 mg, 2.25 mmol), followed by methyl chloroformate (213 mg, 2.25 mmol). The solution was stirred for 2 hr, diluted with ether, and washed with 1M H3PO4. The aqueous lay... | COC(=O)[C@@H]1CN(C(=O)OC)C[C@H]1c1ccc(OC)c(OCCCOc2ccccc2)c1 | null | 76.4 | null |
53,526 | ord_dataset-053897d9b1744303b2fdfe3e796ca27b | null | 1979-01-01T00:04:00 | true | Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:5]=[C:4]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[N:3]=1.[C:34]1([C:40]2[CH:46]=[C:45]([OH:47])[CH:44]=[C:43]([C:48]3[CH:53]=[CH:52][... | Oc1cc(-c2ccccc2)c(O)c(-c2ccccc2)c1 | CCCCCCCCCCCCOc1nc(Cl)nc(OCCCCCCCCCCCC)n1 | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 0 | null | In a 500 ml-three-necked flask 4.8 g (0.01 mole) of the 2-chloro-4,6-dilauroxy-s-triazine prepared above, were mixed with 2.6 g (0.01 mole) of 2,6-diphenyl hydroquinone. After rinsing with nitrogen, 150 ml of acetone were added, followed by adding dropwise, with vigorous stilling, 0.4 g (0.01 mole) of NaOH dissolved in... | CCCCCCCCCCCCOc1nc(OCCCCCCCCCCCC)nc(Oc2cc(-c3ccccc3)c(O)c(-c3ccccc3)c2)n1 | null | null | null |
1,384,138 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.N1CCCCC1.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1>CO>[Cl:17][C:18]1[CH:26]=[C:25]2[C:21](/[C:22](=[CH:5]\[C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=3[F:10])/[C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1 | O=Cc1cccc(Cl)c1F | O=C1Cc2ccc(Cl)cc2N1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | 8 | 3-Chloro-2-fluorobenzaldehyde (6.24 g, 39.4 mmol) was added to a solution of piperidine (3.88 mL, 39.4 mmol) and 6-chlorooxindole (6.0 g, 35.8 mmol) dissolved in methanol (100 mL). After stirring overnight, the resulting solid was filtered and washed with methanol and hexanes to give 10.6 g of (E)-6-chloro-3-(3-chloro-... | O=C1Nc2cc(Cl)ccc2/C1=C\c1cccc(Cl)c1F | null | 96.1 | null |
1,744,902 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[F:6][C:7]1[C:15]([F:16])=[CH:14][C:13]([OH:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:2]1([O:17][C:13]2[CH:14]=[C:15]([F:16])[C:7]([F:6])=[C:8]([CH:12]=2)[C:9]([O:11][CH:2]2[CH2:5][CH2:4][CH2:3]2)=[O:10])[CH2:5][CH2:4][CH2:3]1 | BrC1CCC1 | O=C(O)c1cc(O)cc(F)c1F | 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 | 90 | 8 | Bromocyclobutane (150 g, 1.12 mol) was added to a mixture of 2,3-difluoro-5-hydroxybenzoic acid (50 g, 287 mmol), and potassium carbonate (230 g, 1.67 mol) in acetonitrile (1500 mL), and the resulting mixture stirred overnight at 90° C. The reaction mixture was cooled to room temperature, filtered, and concentrated und... | O=C(OC1CCC1)c1cc(OC2CCC2)cc(F)c1F | null | 60.5 | null |
852,658 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | C([N:3]([CH2:14][CH3:15])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH3:12])C.[OH:16][C@@H:17]1[CH2:21][CH2:20][N:19]([CH2:22]CC(N(OC)C)=O)[CH2:18]1>>[Cl:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]2[C:6]=1[CH:12]=[C:14]([CH2:15][CH2:22][N:19]1[CH2:20][CH2:21][C@@H:17]([OH:16])[CH2:18]1)[NH:3][C:4]2=[O:13] | CCN(CC)C(=O)c1cccc(Cl)c1C | CON(C)C(=O)CCN1CC[C@@H](O)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 the same manner as in Example 16b and using N,N-diethyl-3-chloro-2-methylbenzamide (3.43 g) and (R)-3-(3-hydroxypyrrolidin-1-yl)-N-methoxy-N-methylpropanamide (3.08 g), (R)-5-chloro-3-[2-(3-hydroxypyrrolidin-1-yl)ethyl]-2H-isoquinolin-1-one (102 mg) was obtained. | O=c1[nH]c(CCN2CC[C@@H](O)C2)cc2c(Cl)cccc12 | null | 2.3 | null |
18,066 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([N:15](C)[CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][CH:7]=1)=O.[CH2:26](I)C.CC(C)=O>O>[CH2:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([NH:15][CH2:16][C:17]2([CH3:26])[CH:18]=[CH:19][N:20]=[CH:21][CH2:22]2)=[O:14])=[CH:10][C... | CN(Cc1ccncc1)C(=O)Nc1ccc(NC(=O)C(F)(F)F)cc1 | CCI | null | null | 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 | 8 | To 2.89 gms. (0.01 mole) of 1-(p-trifluoroacetamidophenyl)-3-methyl-3-(4-pyridylmethyl)urea [prepared by reacting 1-(p-aminophenyl)-3-methyl-3- (4-pyridylmethyl)urea (Example 6., supra.) with trifluoroacetic anhydride (method of Hickenbottom, Reactions of Organic Compounds, Longmans, London, 1963)] there is added 6.24 ... | CCNc1ccc(NC(=O)NCC2(C)C=CN=CC2)cc1 | null | null | null |
389,871 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | [N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]... | [N-]=[N+]=NCCCCCc1ccc(Oc2ccccc2)cc1 | null | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | 25 | 84 | To a solution of the product from Step 2 (360 mg, 1.28 mmol) in 10 mL of THF at room temperature was added water (0.025 mL), followed by triphenylphosphine (364 mg, 1.41 mmol). The solution was stirred at room temperature. After 84 hours, the reaction was concentrated in vacuo to provide the titled compound. | NCCCCCc1ccc(Oc2ccccc2)cc1 | null | null | null |
1,267,327 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([NH:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23](=[O:29])[NH:24]2)[C:11]1([C:14]([F:17])([F:16])[F:15])[CH2:13][O:12]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:36]([SH:38])[CH3:37].O>CN(C=O)C>[CH2:36]([S:38][CH2:13][C:11]([OH:12])([C:14](... | COc1ccc(C(Nc2cccc3[nH]c(=O)ccc23)C2(C(F)(F)F)CO2)c(F)c1 | CCS | 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 | O | null | null | null | null | null | null | null | null | null | null | 4 | To 50 mg (0.12 mmol) 5-{[(2-Fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-1H-quinolin-2-one and 80 mg Cs2CO3 in 0.5 ml DMF are added 14 μl (0.18 mmol) of ethyl mercaptan in DMF. The mixture is stirred vigorously for 4 hours and water is added. The aqueous layer is extracted with ethyl acetate, the or... | CCSCC(O)(C(Nc1cccc2[nH]c(=O)ccc12)c1ccc(OC)cc1F)C(F)(F)F | null | 35.4 | null |
603,014 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:15]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1 | O=C1CCC(c2ccc(O)cc2)CC1 | O=C([O-])[O-] | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CC(C)=O | null | null | null | null | null | null | null | null | null | 65 | null | A solution of 4-(4-hydroxyphenyl)cyclohexanone (5.0 g, 26.3 mmol) in acetone (100 mL) was treated with K2CO3 (14.5 g, 105 mmol, 4 equiv) and iodomethane (4.9 mL, 11.2 g, 78.6 mmol, 3 equiv.). The reaction was heated at 65° C. overnight. After the solvent was removed, the residue was treated with H2O and extracted with ... | COc1ccc(C2CCC(=O)CC2)cc1 | null | 99.4 | null |
232,480 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | [C:1]([C:4]1[C:5]([OH:17])=[C:6]([O:15][CH3:16])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2].Cl[CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1)[CH3:23]>C(C(C)=O)C>[C:1]([C:4]1[C:5]([O:17][CH2:19][CH2:20][CH2:21][N:22]... | COc1c(C(C)=O)c(O)c(OC)c2occc12 | COc1ccc(CCN(C)CCCCl)cc1OC | null | null | 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 | 39 g of 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran are refluxed with 40 g of 3-chloropropyl-(2-(3,4-dimethoxyphenyl)-ethyl)-methylamine in 250 ml of methyl ethyl ketone for 14 hours. The mixture is filtered, the solvent is stripped off and the oily residue is dissolved in dilute HCl. The aqueous phase is washed with et... | COc1ccc(CCN(C)CCCOc2c(C(C)=O)c(OC)c3ccoc3c2OC)cc1OC | null | null | null |
1,211,756 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[CH:15]1[C:14]2[N:13]([CH2:10][CH2:11][CH2:12][S:8][C:1](=[O:9])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][... | OC(=S)c1ccccc1 | C=CCn1c2ccccc2c2ccccc21 | null | O=C([O-])O | [Na+] | 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 | null | null | Thiobenzoic acid (30 g, 0.20 mol) was added to 9-allylcarbazole (11.9 g, 0.057 mol) in 100 mL toluene, and the reaction was carried out at 90° C. with argon purge via radical mechanism using AIBN as the initiator (1.8 g, 11 mmol, in 300 mg increments at 1 hr intervals). After 6 hrs the reaction mixture was poured into ... | O=C(SCCCn1c2ccccc2c2ccccc21)c1ccccc1 | null | null | null |
1,158,848 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)[CH3:2].[N:13]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[NH:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])[NH2:13] | O=N[O-] | CCOC(=O)c1cccc(N)c1 | null | Cl | Cl[Sn]Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of m-aminobenzoic acid ethyl ester (200 g, 1.21 mmol) in conc. HCl (200 mL) was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mmol) at 0° C. and the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (662 g, 2.92 mmol) in conc. HCl (2 L) was then added at 0° C. The reaction solution... | CCOC(=O)c1cccc(NN)c1 | null | null | null |
1,601,232 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1]([NH:6][C:7]1[C:8]2[N:9]=[CH:10][N:11]([C:43]=2[N:44]=[CH:45][N:46]=1)[C@:12]1(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:23][C@H:18]([CH2:19][O:20]OC)[C@@H:16]([OH:17])[C@H:13]1[O:14][CH3:15])(=[O:5])[CH2:2][CH2:3][CH3:4].[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>N1C=CC=CC=1>[C:47]([O:17][C... | O=C(Cl)c1ccccc1 | CCCC(=O)Nc1ncnc2c1ncn2[C@]1(C(c2ccccc2)(c2ccccc2)c2ccccc2)O[C@H](COOC)[C@@H](O)[C@H]1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | N-Butyryl-5′-O-monomethoxytrityl-2′-O-methyladenosine 7 (100 mg, 0.16 mmol) was dried by evaporation of added dry pyridine (5 mL) under reduced pressure and finally by keeping on a vacuum pump for 30 min. Dry pyridine was added (2 mL) and the solution was put into ice-bath whereupon benzoyl chloride was added (1.2 eq, ... | CCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OC(=O)c2ccccc2)[C@H]1OC | null | 80 | null |
1,226,908 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | C([O:8][C:9]1[C:10]([F:24])=[C:11]([C:15]2(O)[CH2:20][CH2:19][N:18]([CH2:21][CH3:22])[CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:21]([N:18]1[CH2:17][CH:16]=[C:15]([C:11]2[C:10]([F:24])=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[CH2:20][CH2:19]1)[CH3:22] | CCN1CCC(O)(c2cccc(OCc3ccccc3)c2F)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | Preparation according to preparation 2: 4-[3-(benzyloxy)-2-fluorophenyl]-1-ethylpiperidin-4-ol (1.9 g, 5.77 mmol), trifluoroacetic acid (5 ml). Yield: 1.1 g. MS m/z (rel. intensity, 70 eV) 221 (M+, bp), 220 (43), 206 (95), 163 (10), 110 (14). | CCN1CC=C(c2cccc(O)c2F)CC1 | null | null | null |
1,523,248 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CN(C)C=O>[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5](=[O:8])[N:6]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22]... | Fc1ccc(CBr)cc1 | CN(C)C=Nc1nc(O)ncc1F | 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 | 16 | To an 8 mL screw-cap vial was added N,N-dimethylformamide (DMF; 1.5 mL), N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), anhydrous potassium carbonate (K2CO3; 138 mg, 1.0 mmol), and 4-fluorobenzyl bromide (113 mg, 0.60 mmol). The mixture was shaken and heated to 70° C. for 2 h and the... | CN(C)C=Nc1nc(=O)n(Cc2ccc(F)cc2)cc1F | null | null | null |
1,372,902 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[OH-].[Na+].[C:23]([O:27]C)(=[O:26])[CH:24]=[CH2:25].Cl>O1CCOCC1.ClCCl>[N:16]1[CH:17]=[CH:18][C:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][C@H:2]3[CH2:3][CH2:4][CH2:5]... | C=CC(=O)OC | c1cc(Oc2ccc(OC[C@H]3CCCN3)cc2)ccn1 | null | Cl | [Na+] | [OH-] | 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 | 25 | 8 | The product from Example 144 (50 mg, 0.15 mmol) was treated with 20% NaOH (5 ml) and extracted with EtOAc, dried over Na2SO4 and dried down to give the free base. Dichloromethane (3 ml) and methyl acrylate (0.4 ml, 2.8 mmol) were added and the mixture was stirred at rt overnight. The reaction mixture was dried down to ... | O=C(O)CCN1CCC[C@@H]1COc1ccc(Oc2ccncc2)cc1 | null | null | null |
851,148 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C@H:44]2[O:46][CH2:45]2)=[CH:38][C:37]=1[N:47](C(OC(C)(C... | CCOC(=O)COc1ccc([C@H]2CC[C@H](NCc3ccccc3)CC2)cc1 | CC(C)(C)OC(=O)N(c1cc(OC[C@@H]2CO2)ccc1OCc1ccccc1)S(C)(=O)=O | 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 | 50 | null | A mixture of 3.22 g of ethyl trans-{4-[4-(benzylamino)cyclohexyl]phenoxy}acetate (8.7 mmol) and 5 g of 4-benzyloxy-3-(N-(tert-butoxycarbonyl)-N-(methylsulfonyl)amino)-1-((2S)-2,3-epoxypropoxy)benzene (11.2 mmol) in ethanol (72 ml) is brought to reflux for 40 h. A 3N solution of hydrochloric acid in ethanol is added and... | CCOC(=O)COc1ccc([C@H]2CC[C@H](N(Cc3ccccc3)C[C@H](O)COc3ccc(OCc4ccccc4)c(NS(C)(=O)=O)c3)CC2)cc1 | null | null | null |
1,610,494 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH:1]1([CH:4]([O:20][CH3:21])[CH:5]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9]([C:16]([OH:18])=O)=[C:8]2[CH3:19])[CH3:6])[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:47][CH2:48][C:49]1[C:50](=[O:58])[NH:51][C:52]([CH3:57])=[CH:53][C:54]=1[O:55][CH3:56]>ClCCl>[CH:1]1([CH:4... | COC(C1CC1)C(C)n1c(C)c(C(=O)O)c2cccnc21 | COc1cc(C)[nH]c(=O)c1CN | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | Cl | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.83 | To a solution of 1-(1-cyclopropyl-1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (100 mg, 0.35 mmol) in dichloromethane (2 mL) was added HATU (192 mg, 0.52 mmol), TEA (105.28 mg, 1.04 mmol). After stirred for 50 min at room temperature, 3-(aminomethyl)-4-methoxy-6-methylpyridin-2(1H)-one hyd... | COc1cc(C)[nH]c(=O)c1CNC(=O)c1c(C)n(C(C)C(OC)C2CC2)c2ncccc12 | null | null | null |
233,220 | ord_dataset-ed79ebfb2fff4cdbbc3a609c8edeac11 | null | 1991-01-01T00:08:00 | true | C(OC[C:5]([CH2:27]OCC)([OH:26])[CH:6]([NH:18]C(OC(C)(C)C)=O)[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)C.[ClH:31]>>[ClH:31].[NH2:18][C@H:6]1[CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C@H:27]([Cl:31])[C@H:5]1[OH:26] | CCOCC(O)(COCC)C(Cc1cccc2ccccc12)NC(=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 | 100 | 0.05 | A suspension of α, α-diethoxymethyl-β-tert-butoxycarbonylamino-1-naphthalenepropanol (252 mg), isomer B w as stirred in 37% aqueous hydrochloric acid at 0° C. for 50 minutes. The resulting suspension was then stirred at 100° C. for 3 minutes. The reaction flask was cooled at 0° C. and the precipitate was filtered, wash... | N[C@H]1Cc2c(ccc3ccccc23)[C@H](Cl)[C@H]1O | null | null | null |
509,015 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | [C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]O)[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(OCC)C>[Br:19][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]2[C:1]1=[O:17] | BrP(Br)Br | O=C1c2ccccc2C(=O)N1CCCCCO | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 9 | Then, 16.2 g of 5-phthalimido-1-pentanol was dissolved in 350 ml of diethyl ether, and 4.3 ml of phosphorus tribromide was added dropwise at 0° C. The reaction solution was stirred at room temperature for 9 hours and neutralized with saturated aqueous sodium hydrogen carbonate, and the organic layer was washed with sat... | O=C1c2ccccc2C(=O)N1CCCCCBr | null | 45 | null |
553,150 | ord_dataset-ec9decb576c4424c9685993f6262bd9c | null | 2002-01-01T00:07:00 | true | C(Cl)(Cl)(Cl)Cl.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:28]N1C(=O)CCC1=O>ClCCl>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[C:17]([CH2:20][CH3:21])=[CH:18... | CCc1ccc(OCc2ccccc2)cc1OCCCC#N | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 5.5 | Carbon tetrachloride (30 mL) was used to dissolve 4-(Benzyloxy)-2-[(3-cyanopropyl)oxy]-1-ethylbenzene (2.5 g). N-bromosuccinimide (1.66 g) was added to the solution and it was stirred for 5.5 hours. The mixture was diluted with dichloromethane (50 mL), washed with water, dried over magnesium sulfate, filtered, and conc... | CCc1cc(Br)c(OCc2ccccc2)cc1OCCCC#N | null | 47.4 | null |
783,711 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:22]12([NH2:32])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2>C(O)C>[C:22]12([NH:32][CH2:19][C@@H:17]([OH:18])[CH2:16][O:15][C:12]3[CH:1... | NC12CC3CC(CC(C3)C1)C2 | Fc1ccc2c(-c3ccc(OC[C@H]4CO4)cc3)noc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | Combine (R)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole (29) (250 mg, 0.86 mmol), 1-adamantanamine (530 mg, 3.50 mmol), ethanol (4.0 ml) and heat (˜80° C.) for 16 hours. Cool reaction to room temperature and concentrate (in vacuo). Purify the compound by column chromatography (silica) eluting with 28% aqueo... | O[C@H](CNC12CC3CC(CC(C3)C1)C2)COc1ccc(-c2noc3cc(F)ccc23)cc1 | null | 88.4 | null |
718,304 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | I([O-])(=O)(=O)=O.[Na+].OC[C:9]1([OH:20])[CH:15]=[CH:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH2:10]1>O1CCOCC1.O>[O:11]1[C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH:14]=[CH:15][C:9](=[O:20])[CH2:10]1 | OCC1(O)C=Cc2ccccc2OC1 | null | null | [Na+] | [O-][I+3]([O-])([O-])[O-] | null | 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 | 2 | 4×28.5 mg (0.55 mmol) of sodium periodate are added in four equal portions over 30 minutes to 106 mg (0.55 mmol) of 3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-3-ol, prepared according to example 24, in solution in 3 ml of a 3/7 dioxane/water mixture. After stirring at ambient temperature for 2 hours, the medium is filt... | O=C1C=Cc2ccccc2OC1 | null | 69.2 | null |
1,325,139 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | C(N(CC)CC)C.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH:17]=[CH:16]1>C1(C)C=CC=CC=1>[C:8]1([S:14][CH:17]2[CH2:16][C:15](=[O:21])[O:20][C:18]2=[O:19])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1 | O=C1C=CC(=O)O1 | Sc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 12 | Triethylamine (0.8 ml) was added dropwise to a solution of benzenethiol (9.3 ml, 91 mmol) and maleic anhydride (8.9 g, 91 mmol) in toluene (125 ml). After stirring at room temperature for 12 hr the solvent was evaporated to leave 20 g of crude 3-phenylsulfanyl-dihydro-furan-2,5-dione as a brown oil. 1H NMR (CDCl3) δ 7.... | O=C1CC(Sc2ccccc2)C(=O)O1 | null | 105.5 | null |
735,321 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | CC[N:3](C1C=CC=CC=1)CC.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([OH:20])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH2:3])=[O:20] | O=C(O)c1ccccn1 | CCN(CC)c1ccccc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | 23 | 0.17 | Diethylaniline (0.27 μL, 1.7 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (0.8 mg, 1.5 μmol, 1 equiv) in THF (0.15 mL) at 0° C. under an argon atmosphere and the solution was stirred for 10 min. Picolinic acid (0.24 mg, 2.0 μmol, 1.3 equiv), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimid... | NC(=O)c1ccccn1 | null | 481.7 | null |
1,201,411 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)[NH2:19])([CH3:15])[CH3:14]>>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([NH:19][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[OH:11])[CH:20]=[C... | CC(C)(C)c1cc(N)cc(C(C)(C)C)c1 | O=C(O)c1cc(Cl)ccc1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Using 5-chlorosalicylic acid and 3,5-bis[(1,1-dimethyl)ethyl]aniline as the raw materials, the same operation as the example 16 gave the title compound. | CC(C)(C)c1cc(NC(=O)c2cc(Cl)ccc2O)cc(C(C)(C)C)c1 | null | 34.1 | null |
1,553,040 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH:24]=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][OH:25])([CH2:18][CH2:19... | O=CCCC12CCC(c3cccc(Oc4ccccc4)c3)(CC1)OC2 | null | null | CC(C)C[AlH]CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | -78 | 2 | To a solution of 3-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal (40 mg, 0.119 mmol) in DCM (1 mL) at −78° C. under N2 was added 1M DIBAL-H in DCM (0.178 ml, 0.178 mmol). The reaction mixture was stirred at −78° C. for 2 h and then added CELITE® (250 mg). The reaction was quenched with sat′d aqueous NH4Cl... | OCCCC12CCC(c3cccc(Oc4ccccc4)c3)(CC1)OC2 | null | 99.3 | null |
1,386,813 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | CC([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)[C:15](=[O:17])[O-:16])(C)C.[CH:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27]>>[CH2:7]1[C:8]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH:6]1[N:14]([CH2:18][C:19]... | CC(C)(C)C1c2ccccc2CC1N(Cc1ccc(Br)cc1)C(=O)[O-] | O=Cc1cccc(B(O)O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 1,1-dimethylethyl[(4-bromophenyl)methyl]2,3-dihydro-1H-inden-2-ylcarbamate (Example V-13) and 3-formylphenylboronic acid according to the procedure described in Example VI-16 Step 1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (s, 9H), 3.00 (d, J=8.56 Hz, 4H), 4.51 (br. s., 2H), 7.06-7.19 ... | CC(C)(C)OC(=O)N(Cc1ccc(-c2cccc(C=O)c2)cc1)C1Cc2ccccc2C1 | null | null | null |
985,432 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | CC1(C)CCCC(C)(C)N1.C([Li])CCC.[CH:16]1[CH:21]=[N:20][CH:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[C:33]1([C:36]([N:38]2[CH2:42][CH2:41][C:40](=O)[CH2:39]2)=[O:37])[CH2:35][CH2:34]1.Cl>CCCCCC.C1COCC1>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]... | O=C1CCN(C(=O)C2(c3ccc(Cl)cc3Cl)CC2)C1 | O=C(O)c1cccnc1 | null | CC1(C)CCCC(C)(C)N1 | Cl | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | C1CCOC1 | null | null | null | null | null | null | null | null | null | -55 | 0.25 | To a solution of 2,2,6,6-tetramethyl-piperidine, (1.18 mL, 0.00700 mol) in tetrahydrofuran (30 mL, 0.4 mol) at −78° C. was added n-butyllithium in hexane (2.5 M, 3.7 mL). After stirring for 15 min., a suspension of niacin (0.287 g, 0.00233 mol) in THF was added and the mixture was stirred at −78° C. for 10 min. The rea... | O=C1OC2(CCN(C(=O)C3(c4ccc(Cl)cc4Cl)CC3)C2)c2ccncc21 | null | null | null |
1,118,179 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1)#[N:2].[ClH:16]>O1CCOCC1>[ClH:16].[NH:5]1[CH2:6][CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4]1 | CC(C)(C)OC(=O)N1CCCC(C#N)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | 0 | 2 | A 250-mL 3-necked round-bottomed flask was charged with tert-butyl 3-cyanopiperidine-1-carboxylate (5.8 g, 27.07 mmol, 1.00 equiv, 98%) in 1,4-dioxane (60 mL). The mixture was cooled down to at 0° C. and treated with HCl (g). The mixture was stirred for 2 hours at 0° C. resulting in a precipitate that was collected by ... | N#CC1CCCNC1 | null | 48 | null |
489,584 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.[I:25]I.Cl>CCCCCC.C1COCC1>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[C:14]([F:19])[C:15]([I:25])=[C:16]([F:18])[CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH... | II | CCCCCC1CCC(c2cc(F)cc(F)c2)CC1 | null | Cl | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCCC | null | null | null | null | null | null | null | null | null | null | 0.5 | To a mixture of (4-pentyl-cyclohexyl)-3,5-difluorobenzene (10 mmol) and 150 ml of THF, was added dropwise 7.5 ml of a solution of n-butyl lithium (corresponding to 12 mmol) in hexane while keeping them at a temperature lower than −70° C., and stirred at the same temperature for 30 min. While keeping the solution at a t... | CCCCCC1CCC(c2cc(F)c(I)c(F)c2)CC1 | null | 83 | null |
968,153 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl.[NH2:2][CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:2][CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])(=[O:26])=[O:25])=[CH:20][CH:19]=1 | O=S(=O)(Cl)c1ccc(Cl)cc1 | CCC(N)C(=O)OC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | Methyl 2-aminobutanoate hydrochloride 56 (25 g, 0.163 mol) was suspended in CH2Cl2 (100 mL) and triethylamine (50 mL) and 4-chlorobenzenesulfonyl chloride (37.8 g, 1.1 eq) were added to the mixture. The mixture was stirred at room temperature overnight. Diluted with 200 mL of CH2Cl2 and washed with water (3×50 mL), sat... | CCC(NS(=O)(=O)c1ccc(Cl)cc1)C(=O)OC | null | null | null |
506,958 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:17])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>C1COCC1>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:4]([CH2:28][C:29]2[CH:36]=[CH:35][CH:34]=[C:3... | Cc1cccc(CBr)c1 | COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | null | C[Si](C)(C)[N-][Si](C)(C)C | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 8 | To a cold (−78° C.) solution of methyl N-tert-butoxycarbonyl-piperidine-4-carboxylate (5.0 g, 20.5 mmol; Example 3, Step B) in anhydrous THF (70 mL), a solution of sodium bis(trimethylsilyl)amide (20.5 mL, 1M, 20.5 mmol) was added over a period of 30 min. The resultant mixture was stirred at −78° C. for 1 h., and 3-met... | COC(=O)C1(Cc2cccc(C)c2)CCN(C(=O)OC(C)(C)C)CC1 | null | null | null |
973,588 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C(N(CC)CC)C.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[S:48]... | CC(C)(C)OC(=O)n1c(-c2ccc(O)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21 | O=S(=O)(Cl)c1ccccn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | In a similar manner to Step 1 of Example 227, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0728 g, 0.158 mmol) was dissolved in acetonitrile (2.0 mL), and the solution was treated with triethylamine (0.0660 mL, 0.473 mmol) and 2-pyridinesulfonyl chloride (0.0680 g, 0.315 mmol) to... | CC(C)(C)OC(=O)n1c(-c2ccc(OS(=O)(=O)c3ccccn3)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21 | null | 733 | null |
1,390,317 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[CH2:14]1[CH:18]2[CH2:19][CH:20]([NH2:21])[CH:16]([CH2:17]2)[CH2:15]1>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C@H:16]12[CH2:17][C@H:18]([CH2:14][CH2:15]1)[CH2:19][C@H:20]2[NH:21][CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2... | NC1CC2CCC1C2 | C#C[C@H]1CC[C@@H](C#N)N1C(=O)CCl | null | CCCC[N+](CCCC)(CCCC)CCCC | [I-] | 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 | 25 | 18 | To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.03 g, 0.152 mmol) in acetonitrile (1 mL) at room temperature was added exo-2-aminonorborane (0.036 mL, 0.305 mmol) and a catalytic amount of tetrabutylammonium iodide. The reaction mixture was stirred at room temperature for 18 hou... | C#C[C@H]1CC[C@@H](C#N)N1C(=O)CN[C@@H]1C[C@H]2CC[C@@H]1C2 | null | null | null |
271,816 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.B.[Na].Cl.[CH2:12](O)[CH3:13]>>[CH:12]1([CH2:13][NH:1][CH2:2][C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:6][CH2:7][CH2:8][CH2:3][CH2:2]1 | CCO | NCc1cccnc1 | null | B | Cl | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | To 100 ml of ethanol were added 7.0 g of cyclooctylaldehyde and 5.4 g of 3-aminomethylpyridine, and the mixture was subjected to a reaction for 4 hours at about 50° C. After cooling, 2.0 g of sodium boron hydride was added while 20° C. or below was kept by ice cooling, and the mixture was subjected to a reaction for 1 ... | c1cncc(CNCC2CCCCC2)c1 | null | null | null |
1,621,995 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | Cl[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:4]([NH:25][C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)[N:3]=1.[NH2:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@@H:35]1[NH:40][C:41](=[O:47])[O:42]... | CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1N | CCOC(=O)c1c(CN2C(=O)c3ccccc3C2=O)nc(Cl)nc1Nc1cccc(C)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 80 | 3 | A mixture of ethyl 2-chloro-4-((1,3-dioxoisoindolin-2-yl)methyl)-6-(m-tolylamino)pyrimidine-5-carboxylate (96.3 mg, 0.214 mmol), tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (58.14 mg, 0.271 mmol) and Et3N (0.030 mL, 0.214 mmol) in DMA (2 mL) was stirred at 80° C. for 3 h. Saturated aq NaHCO3 was added to the mixture,... | CCOC(=O)c1c(CN2C(=O)c3ccccc3C2=O)nc(N[C@@H]2CCCC[C@@H]2NC(=O)OC(C)(C)C)nc1Nc1cccc(C)c1 | null | 92 | null |
1,355,049 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][NH:5][C:6]1[N:15]=[C:14]2[C:9]([C:10](=[O:29])[C:11]([C:24]([O:26]CC)=[O:25])=[CH:12][N:13]2[CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH2:22][CH3:23])=[CH:8][C:7]=1[I:30].C1COCC1.[Li+].[OH-]>CO>[CH3:31][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]1[N:15]=[C:14]2[C:9]([C:10](=[O:29... | CCOC(=O)c1cn(C[C@@H]2CCCN2CC)c2nc(NCCN(C)C)c(I)cc2c1=O | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 0.5 | (S)-ethyl 7-(2-(dimethylamino)ethylamino)-1-((1-ethylpyrrolidin-2-yl)methyl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 40) was then taken up in methanol (2 mL) and THF (5 mL) and 1 ml of 2N LiOH was added and stirred at room temperature for 30 min. The solvent was removed in vacuo to give (... | CCN1CCC[C@H]1Cn1cc(C(=O)O)c(=O)c2cc(I)c(NCCN(C)C)nc21 | null | null | null |
44,299 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | [Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:6]1[C:19]2[C:10](=[NH+:11][CH:12]=[C:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[CH:14]3)[CH:9]=[CH:8][CH:7]=1.[C:20]1([C:26]([CH3:31])=[CH:27][C:28](=O)[CH3:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH3:29][C:28]1[N+:11]2[C:10]3[CH:9]=[CH:8][C... | c1ccc2c(c1)c[nH+]c1ccccc12 | CC(=O)C=C(C)c1ccccc1 | null | [O-][Cl+3]([O-])([O-])[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Phenanthridinium perchlorate (2 g) and 4-phenylpent-3-ene-2-one (4 g) were heated together at 150° for 16 hours. The reaction mixture was cooled and diluted with methanol. The product was isolated by filtration and recrystallized from acetonitrile. Yield 1.5 g, m.p. 252°-3°. | Cc1cc(-c2ccccc2)cc2c3ccccc3c3ccccc3[n+]12 | null | null | null |
957,142 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [Cl:1][C:2]1[N:12]=[C:11]2[C:5]([NH:6][C:7](=[O:19])[CH2:8][CH2:9][N:10]2[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.[CH3:20]I.[H-].[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH2:9][N:10]2[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1 | CI | O=C1CCN(C2CCCCC2)c2nc(Cl)ncc2N1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 5 | 16 | 10-chloro-2-cyclohexyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 267; 5.87 g, 20.91 mmol) was suspended in DMA (450 mL) under nitrogen. Methyl iodide (3.26 g, 23 mmol) was added and the suspension cooled to 5° C. on an ice-water bath. Sodium hydride (60% mineral oil dispersion; 920 mg, 23 mm... | CN1C(=O)CCN(C2CCCCC2)c2nc(Cl)ncc21 | null | 81.4 | null |
289,122 | ord_dataset-96711be098434bc9ab567cb77fa3362b | null | 1994-01-01T00:04:00 | true | [F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[S:10]1[CH2:16][C:14](=[O:15])[NH:13][C:11]1=[S:12].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:16]2[S:10][C:11](=[S:12])[NH:13][C:14]2=[O:15])=[CH:4][CH:3]=1 | O=C1CSC(=S)N1 | O=Cc1ccc(F)cc1 | null | CC(=O)[O-] | [Na+] | 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 | null | 10 g of 4-fluorobenzaldehyde was dropwise added at room temperature to a solution having 10.8 g of rhodanine and 20 g of sodium acetate suspended in 100 ml of acetic acid. The obtained mixture was reacted under reflux for two hours and then cooled to room temperature. Then, this reaction mixture was put into about 500 ... | O=C1NC(=S)SC1=Cc1ccc(F)cc1 | null | 85.1 | null |
435,186 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OC1C=NC(C2C=CC(O[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][O:49][CH2:50][C:51]([O:54][C:55]([F:68])([F:67])[C:56]([F:66])([F:65])[O:57][C:58]([F:64])(... | CCCCCCCCOc1cnc(-c2ccc(O)c(F)c2)nc1 | CCCCCCOc1cnc(-c2ccc(OCCCCCOCC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)F)cc2)nc1 | null | null | null | null | null | null | null | 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 essentially as in Example 1 by combining 5-octyloxy-2-[4-hydroxy-3-fluorophenyl)pyrimidine (1.5 g, 4.7 mmol) with 5-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentyl chloride (2.45 g, 5.1 mmol, Example 22). The reaction mixture was quenched with water, and the resulti... | CCCCCCCCOc1cnc(-c2ccc(OCCCCCOCC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)F)c(F)c2)nc1 | null | null | null |
1,035,089 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [F:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]2[S:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.S(Cl)([Cl:15])=O>CN(C)C=O>[Cl:15][C:8]1[S:9][C:5]2[C:4]([F:12])=[CH:3][C:2]([F:1])=[CH:11][C:6]=2[N:7]=1 | Fc1cc(F)c2sc(S)nc2c1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | 48 | To a suspension of 2 g (9.841 mmol) 5,7-difluoro-benzothiazole-2-thiol in 10.7 mL (147.6 mmol) thionyl chloride was added drop wise 215 □L N,N-dimethylformamide at room temperature. The mixture was stirred at room temperature for 2 days. The solvent was removed in vacuo. The crude compound was purified with flash colum... | Fc1cc(F)c2sc(Cl)nc2c1 | null | 32.6 | null |
1,536,279 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [H-].[Na+].[OH:3][CH:4]([CH2:8][S:9][CH3:10])[C:5]([OH:7])=[O:6].I[CH3:12]>CN(C=O)C>[CH3:12][O:3][CH:4]([CH2:8][S:9][CH3:10])[C:5]([OH:7])=[O:6] | CSCC(O)C(=O)O | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 0.17 | To a stirred solution of sodium hydride (0.176 g, 4.41 mmol) in DMF (5 mL) was added a solution of 2-hydroxy-3-(methylthio)propanoic acid (0.25 g, 1.836 mmol) in 1 mL DMF at 25° C. and stirred for 10 min Vigorous bubbling was observed upon addition of NaH. Then iodomethane (0.126 mL, 2.020 mmol) was added and the solut... | COC(CSC)C(=O)O | null | 45.7 | null |
1,559,765 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [C:1]1([C@H:7]([NH:41][C:42]([O:44][C@@H:45]2[CH:50]3[CH2:51][CH2:52][N:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:43])[C:8]2[CH:9]=[C:10]([CH:38]=[CH:39][CH:40]=2)[O:11][CH2:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH2:29][CH2:30][CH:31]4OCC[O:32]4)=[O:26])[CH2:21][CH2:20]3)... | O=C(N[C@@H](c1ccccc1)c1cccc(OCc2ccc(C(=O)N3CCC(C(=O)OCCCC4OCCO4)CC3)cc2)c1)O[C@H]1CN2CCC1CC2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a solution of 3-(1,3-dioxolan-2-yl)propyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate in THF (4.7 mL) was added 2 M aqueous hydrochloric acid (4.7 mL). The reaction mixture was stirred at RT for 4 hours. The reaction mixture was partitioned bet... | O=CCCCOC(=O)C1CCN(C(=O)c2ccc(COc3cccc([C@@H](NC(=O)O[C@H]4CN5CCC4CC5)c4ccccc4)c3)cc2)CC1 | null | null | null |
1,247,830 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](O)=O)[C:9]=2[CH3:24])=[CH:4][CH:3]=1.[CH2:25]([NH:28][C:29]([CH3:34])([CH3:33])[C:30]([NH2:32])=[O:31])[CH:26]=[CH2:27]>>[CH2:25]([N:28]1[C:29]([CH3:34])([CH3:33])[C:30](=[O:31])[N:32]=[C:21]1[C... | C=CCNC(C)(C)C(N)=O | Cc1c(C(=O)O)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Compound 10 was synthesized from 4a (253 mg, 0.66 mmol) and 5e (148 mg, 1.05 mmol) as a white solid (171 mg, 53%) in a manner similar to that described in Example 36. 1H NMR (600 MHz, CDCl3) δ 7.41 (d, 1H), 7.27-7.23 (m, 3H), 7.13 (d, 1H), 7.04 (d, 2H), 5.93-5.88 (m, 1H), 5.13-5.07 (m, 2H), 4.54 (d, 2H), 2.37 (s, 3H), ... | C=CCN1C(c2nn(-c3ccc(Cl)cc3Cl)c(-c3ccc(Cl)cc3)c2C)=NC(=O)C1(C)C | null | null | null |
1,050,220 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | C([Li])CCC.Br[C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>O1CCCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1 | Clc1cccc(CBr)c1 | Brc1ccc(C2OCCO2)s1 | null | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 0.33 | n-Butyl lithium (2.6N hexane solution, 15.6 mL, 39 mmol) was added dropwise to a solution of 2-(5bromo-thiophen-2-yl)-[1,3]dioxolane (7.0 g, 30 mmol) in tetrahydrofuran (40 mL) at from −75° to −68° C., and the solution was stirred for 20 minutes. 3-Chlorobenzyl bromide (4.3 mL, 33 mmol) was added dropwise to this react... | Clc1cccc(Cc2ccc(C3OCCO3)s2)c1 | null | 19 | null |
18,973 | ord_dataset-8ca24382d55b4303bc34393399f4110e | null | 1977-01-01T00:01:00 | true | [OH:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[CH:4]([CH3:13])[CH2:3]1.[H-].[Na+].S(OC)(O[CH3:21])(=O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1C=CC=CC=1>[CH3:21][O:1][C:2]1([CH3:14])[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[C:4](=[CH2:13])[CH2:3]1 | CC1=C2CCC(C)(O)CC(C)C2CC1 | COS(=O)(=O)OC | null | O=C(O)CC(O)(CC(=O)O)C(=O)O | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 9.6 g of 6-hydroxy-1,6-dimethyl-4-methyl-2,3,3a,4,5,6,7,8-octahydroazulene in 300 ml of absolute benzene were heated to reflux for 15 hours with 4.8 g of sodium hydride (50% paraffin-containing paste, purified by washing with benzene). Then 95 ml of freshly distilled dimethyl sulphate were added at 40°. The mixture was... | C=C1CC(C)(OC)CCC2=C(C)CCC12 | null | 74 | null |
1,669,616 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.Br[C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>CS(C)=O.ClCCl.[Cl-].[NH4+].[Cu]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][N:3]=1 | CCOC(=O)C(F)(F)Br | Nc1ncc(I)cn1 | null | [Cu] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CS(C)=O | null | null | null | null | null | null | null | null | null | 80 | null | To the Schlank flask containing 2-amino-5-iodopyrimidine (2.210 g, 10.00 mmol) and copper powder (0.953 g, 15.0 mmol) in anhydrous DMSO (10 mL) was added ethyl bromodifluoroacetate (1.285 mL, 10.00 mmol). The reaction mixture was heated at 80° C. under nitrogen overnight. Reaction mixture was cooled to room temperature... | CCOC(=O)C(F)(F)c1cnc(N)nc1 | null | null | null |
1,001,673 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15].[Cl:17][C:18]1[C:19]([F:26])=[C:20]([NH:24]N)[CH:21]=[CH:22][CH:23]=1>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:24][C:20]3[C:21]([C:11]=2[CH2:12][CH3:13])=[CH:22][... | CCCC(=O)c1ccc(C(=O)OC)c(O)c1 | NNc1cccc(Cl)c1F | null | [Cl-] | [Zn+2] | 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 | 120 | null | A mixture of 4-butyryl-2-hydroxy-benzoic acid methyl ester (60 mg, 0.27 mmol), (3-chloro-2-fluoro-phenyl)-hydrazine (Apollo Scientific, Ltd., 54 mg, 0.27 mmol), and zinc chloride (110 mg, 0.8 mmol) in acetic acid (2 mL) is purged with nitrogen for 5 minutes and then heated in a sealed tube at 120° C. for 2 hours. The m... | CCc1c(-c2ccc(C(=O)OC)c(O)c2)[nH]c2c(F)c(Cl)ccc12 | null | null | null |
228,021 | ord_dataset-d98d003e9abb4b579746c5a361466e14 | null | 1991-01-01T00:05:00 | true | [CH3:1][C:2]1[C:13](=[O:14])[C:6]2[N:7]3[CH2:12][CH2:11][CH2:10][C:8]3=[N:9][C:5]=2[C:4](=[O:15])[CH:3]=1.[CH2:16]1[NH:18][CH2:17]1.CC(C)=O.[K+].[Br-]>CO>[N:18]1([C:3]2[C:4](=[O:15])[C:5]3[N:9]=[C:8]4[CH2:10][CH2:11][CH2:12][N:7]4[C:6]=3[C:13](=[O:14])[C:2]=2[CH3:1])[CH2:16][CH2:17]1 | CC1=CC(=O)c2nc3n(c2C1=O)CCC3 | C1CN1 | null | [Br-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 0.5 | To a solution of 35 mg (0.17 mmol) of 26 in 4 mL of dry methanol, chilled at 0° C., was added 0.5 mL of ethyleneimine. The reaction was stirred at 0° for 30 min and then at room temperature for 1 hour. The solvent was removed in vacuo and the red residue flash chromatographed on silica gel using chloroform as the eluan... | CC1=C(N2CC2)C(=O)c2nc3n(c2C1=O)CCC3 | null | null | null |
1,163,259 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[CH:13][N:12]=2)[CH:4]=1)[CH3:2].[CH:20]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH:20]1([NH:25][C:17]([C:14]2[CH:15]=[CH:16][C:11]([C:5]3[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=3[CH3:10])=[N:12][CH... | CCc1cc(-c2ccc(C(=O)O)cn2)c(C)[nH]c1=O | NC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Method 1, Example 205 is substantially repeated except for utilizing 5′-ethyl-2′-methyl-6′-oxo-1′,6′-dihydro-[2,3′]bipyridinyl-5-carboxylic acid and cyclopentyl amine to afford the title compound. MS: m/e=326 (M+H). | CCc1cc(-c2ccc(C(=O)NC3CCCC3)cn2)c(C)[nH]c1=O | null | null | null |
1,298,669 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[H-].[Na+].[CH2:14](I)[CH3:15]>CN(C)C=O>[CH2:14]([N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][C:3]1=[O:11])[CH3:15] | O=C1COc2ccccc2N1 | CCI | 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 | 1 | To a cooled solution of 2H-1,4-benzoxazin-3(4H)-one (11.93 g, 80 mmol) in N,N-dimethylformamide (120 ml) was added sodium hydride (60% dispersion in mineral oil, 3.2 g, 80 mmol) in portions between 0° C. and 5° C. (1 h). The mixture was stirred 1 h at 0° C. To the cooled mixture was added ethyl iodide (13.7 g, 88 mmol)... | CCN1C(=O)COc2ccccc21 | null | 93.8 | null |
1,006,598 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:10][CH:9]=1)=[O:6].[F:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[C:33]([CH3:40])[CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O... | O=C(Nc1ccc(OCCN2CCOCC2)c2ccccc12)c1cccc(Br)c1 | Cc1cc(F)ccc1B(O)O | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | null | 3-Bromo-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-benzamide (600 mg, 1.31 mmol), 4-fluoro-2-methylphenyl boronic acid (271 mg, 1.98 mmol), cesium carbonate (730 mg, 2.24 mmol) and tetrakis triphenylphosphine palladium(0) (25 mg) in dioxane (10 ml) are heated to 100° C. under a nitrogen atmosphere for 16 hours. Th... | Cc1cc(F)ccc1-c1cccc(C(=O)Nc2ccc(OCCN3CCOCC3)c3ccccc23)c1 | null | 69.3 | null |
105,393 | ord_dataset-4ac1b977dc504cb5a6a8e85d7d777c45 | null | 1983-01-01T00:05:00 | true | [CH3:1][C:2]([C@H:18]1[C:21](=[O:22])[NH:20][C@@H:19]1[CH2:23][C:24](=[O:39])[CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:27])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6])[CH3:3].C1(C)C=CC(S([N:49]=[N+:50]... | CC(C)(OC(=O)OCc1ccc([N+](=O)[O-])cc1)[C@H]1C(=O)N[C@@H]1CC(=O)CC(=O)OCc1ccc([N+](=O)[O-])cc1 | Cc1ccc(S(=O)(=O)N=[N+]=[N-])cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 0 | 0.08 | To a solution of 4-nitrobenzyl 4-{(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidine-2-yl}-3-oxobutanoate (58.3 mg) in acetonitrile (1.17 ml) was added a solution of p-toluenesulfonyl azide (25.3 mg) in acetonitrile (0.228 ml) at 0° C. After stirring for 5 minutes at 0° C., a solution of triethyla... | CC(C)(OC(=O)OCc1ccc([N+](=O)[O-])cc1)[C@H]1C(=O)N[C@@H]1CC(=O)C(=[N+]=[N-])C(=O)OCc1ccc([N+](=O)[O-])cc1 | null | 95.6 | null |
970,281 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH:1]1([N:4]2[C:9]3[CH:10]=[CH:11][C:12]([O:14]C)=[CH:13][C:8]=3[S:7](=[O:17])(=[O:16])[NH:6][CH2:5]2)[CH2:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)(Cl)Cl>[CH:1]1([N:4]2[C:9]3[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=3[S:7](=[O:16])(=[O:17])[NH:6][CH2:5]2)[CH2:3][CH2:2]1 | COc1ccc2c(c1)S(=O)(=O)NCN2C1CC1 | null | null | BrB(Br)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | O | null | null | null | null | null | null | null | null | null | null | 20 | A solution of the compound of Example 84 (50 mg) in chloroform (3 mL) is cooled on an ice bath and then boron tribromide (0.15 mL) is added. After stirring for 20 hours, water (5 mL) is added to the mixture, which is then concentrated under reduced pressure and subsequently extracted with ethyl acetate (3×20 mL). The o... | O=S1(=O)NCN(C2CC2)c2ccc(O)cc21 | null | null | null |
1,052,826 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][O:2][C:3](=[O:22])[C@H:4]([NH:18][C:19](=[O:21])[CH3:20])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)(Cl)Cl.C(=O)=O>CO>[C:19]([NH:18][C:4](=[C:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([O:2][CH3:1]... | COC(=O)[C@H](NC(C)=O)C(c1ccccc1)c1ccccc1 | null | null | O=C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | (R)-2-Acetylamino-3,3-diphenylpropionic acid methyl ester, reaction time 6 h, conversion 100%. [α]D25-101.6 (c=1.02, CHCl3). ee 80.7% (SFC, 2× Chiralpak AD-H columns, 10% methanol, 3000 psi CO2, 35° C., flow rate 3 ml/minute, retention times R 5.2 minutes, S 10.1 minutes). Comparative examples have been disclosed by Bo... | COC(=O)C(NC(C)=O)=C(c1ccccc1)c1ccccc1 | null | null | null |
424,274 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | Cl.Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:36]>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:... | COc1cc(N)c(Cl)cc1C(=O)NCC1CCNCC1 | O=C(CCCCCBr)c1ccccc1 | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (2.0 g) as starting compound, potassium carbonate (1.9 g) and 6-bromo-1-phenyl-1-hexanone (1.7 g) were reacted and treated in the same manner as in Example 172 to give 0.56 g of 4-amino-5-chloro-2-methoxy-N-((1-(6-oxo-6-phenylhexyl)piperidin-4... | COc1cc(N)c(Cl)cc1C(=O)NCC1CCN(CCCCCC(=O)c2ccccc2)CC1 | null | 22 | null |
1,114,646 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C... | OB(O)c1ccccc1 | NC(=O)c1cc(Br)cc2c(C3CCS(=O)(=O)CC3)c[nH]c12 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 150 | null | To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (80 mg, 0.216 mmol) in dioxane and water (4 mL/1 mL) was added phenylboronic acid (36 mg), Pd(PPh3)4 (25 mg) and K2CO3 (104 mg). The reaction mixture was heated to 150° C. for 20 minutes by microwave irradiation. The organic phase was separa... | NC(=O)c1cc(-c2ccccc2)cc2c(C3CCS(=O)(=O)CC3)c[nH]c12 | null | 28.9 | null |
1,611,218 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH3:1][CH:2]([CH2:6][CH2:7][C:8]([CH3:12])=[C:9]([CH3:11])[CH3:10])[CH2:3][CH:4]=[O:5].C(O)(=O)C1C=CC=CC=1>CCCCCCC>[CH3:1][CH:2]([CH2:6][CH2:7][C:8]([CH3:12])=[C:9]([CH3:11])[CH3:10])[CH2:3][CH2:4][OH:5] | CC(C)=C(C)CCC(C)CC=O | null | null | O=C(O)c1ccccc1 | 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 | 100 | null | 3,6,7-trimethyloct-6-enal (168 g, 1 mol.), heptane (168 g, 100 wt. %, technical grade), benzoic acid (3.05 g, 25 mmol, 2.5 mol.%) and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium(bispivalate) (9.5 mg, 0.0125 mmol, 0.00125 mol.%) were loaded altogether in a 11 autoclave equipped with a mechanical stirrin... | CC(C)=C(C)CCC(C)CCO | null | null | null |
637,826 | ord_dataset-a192df1b44174b5886ef2005f759d553 | null | 2004-01-01T00:05:00 | true | [C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][CH:6]([OH:10])[CH2:7][CH2:8][CH3:9])#[N:2]>CS(C)=O.C(N(CC)CC)C>[C:1]([C:3]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])#[N:2] | CCCC(O)CCC(C#N)(c1ccccc1)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 1 | 7-Cyano-8-methyl-7-phenylnonane-4-ol, 70 mg 0.27 mmol, was dissolved in dimethyl sulfoxide 3.00 ml and triethylamine 0.70 ml. A sulfur trioxide-pyridine complex 64.7 mg was added thereto. After 1 hour, an additional sulfur trioxide-pyridine complex 80.0 mg was added thereto. The reaction mixture was partitioned by addi... | CCCC(=O)CCC(C#N)(c1ccccc1)C(C)C | null | null | null |
1,602,380 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH2:1]([Li])CCC.[CH:6]1([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=O)[CH2:8][CH2:7]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:6]1([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13... | [Li]CCCC | CC(C)(C)OC(=O)N1CCC(C(=O)C2CC2)CC1 | null | C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 8 | Dissolve methyltriphenylphosphonium bromide (20.26 g, 55.6 mmol) in THF (200 mL) and cool to −78° C. Add butyllithium (20.2 mL, 50.5 mmol) and stir at −78° C. for 15 minutes. Warm to ambient temperature and add a solution of tert-butyl 4-(cyclopropylcarbonyl)piperidine-1-carboxylate in THF (5 mL) dropwise. Stir the mix... | C=C(C1CC1)C1CCN(C(=O)OC(C)(C)C)CC1 | null | 83.5 | null |
142,086 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]CC)=[C:14]([CH3:21])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]>Br>[Cl:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C... | CCOc1ccc(Cn2c(-c3ccccc3)nc(Cl)c2CC(=O)O)cc1C | null | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-Chloro-1-(4-ethoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (10 g) was stirred in 90 ml of 57% hydrobromic acid at 80°-90° C. for 6 hours. The reaction mixture was evaporated to dryness under reduced pressure and the residue was dissolved in 200 ml of ethyl acetate and washed three times with water. The ethyl ... | Cc1cc(Cn2c(-c3ccccc3)nc(Cl)c2CC(=O)O)ccc1O | null | 32.4 | null |
59,132 | ord_dataset-28b19b59e93c47698a5a2b21048ec201 | null | 1979-01-01T00:10:00 | true | [CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]12([CH3:17])[C:13]([CH3:15])([CH3:14])[CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[NH2:16]>C(OC(C)C)(C)C>[C:7]12([CH3:17])[C:13]([CH3:14])([CH3:15])[CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[NH:16][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1] | CC1(C)C2CCC1(C)C(N)C2 | C=C1CC(=O)O1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)OC(C)C | null | null | null | null | null | null | null | null | null | null | 20 | 4 | 16.8 g of diketene were added with stirring to a mixture of 30 g of 2-bornylamine and 200 ml of isopropyl ether and after stirring for 4 hours at 20° C., the mixture was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and elution with a 9-1 methylene chloride-acetone mixtur... | CC(=O)CC(=O)NC1CC2CCC1(C)C2(C)C | null | 83.9 | null |
1,044,019 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | Br[CH2:2][CH2:3][CH2:4][S:5](=[O:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[N:6][C:7](=[O:31])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]3[O:26][CH:27]=[CH:28][C:29]=3[CH3:30])=[O:24])[CH:17]=2)[CH:11]=[N:10][CH:9]=1.[F:39][CH:40]1[CH2:45][CH2:44][CH2:43][NH:42... | Cc1ccoc1C(=O)Nc1cccc(C#Cc2cncc(C(=O)N=S(=O)(CCCBr)c3ccccc3)c2)c1 | FC1CCCNC1 | null | null | null | null | null | null | null | 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 similar to that described for example 508, N-[(3-bromopropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide and 3-fluoropiperidine were converted to the title compound. | Cc1ccoc1C(=O)Nc1cccc(C#Cc2cncc(C(=O)N=S(=O)(CCCN3CCCC(F)C3)c3ccccc3)c2)c1 | null | null | null |
172,762 | ord_dataset-7860c6f563014da8948ede63b7110bde | null | 1988-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]3[CH2:22][CH2:23][CH2:24][C:18]=3[NH:17][C:16]2=[O:25])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].S(OC)(O[CH3:30])(=O)=O.[Na]>C(O)(C)C>[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]3[CH2:22][CH2:23][CH2:24][C:18]=... | COS(=O)(=O)OC | CC(C)OC(=O)c1cc(-n2c(=O)[nH]c3c(c2=O)CCC3)c(Cl)cc1Cl | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | using isopropyl 2,4-dichloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate and dimethyl sulphate with sodium isopropylate in isopropanol there is obtained isopropyl 2,4-dichloro-5-(1,2,4,5,6,7-hexahydro-1-methyl-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate, 1H-NMR (CDCl3, 400 MHz, 7.... | CC(C)OC(=O)c1cc(-n2c(=O)c3c(n(C)c2=O)CCC3)c(Cl)cc1Cl | null | null | null |
1,349,758 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([O:11][C:12]([F:15])([F:14])[F:13])[CH:5]=1.Cl.[CH3:18][NH:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N:19]([CH3:20])[CH3:18])=[C:6]([O:11][C:12]([F:15])([F:14])[F:13])[CH:5]=1 | COC(=O)c1ccc(F)c(OC(F)(F)F)c1 | CNC | null | Cl | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 60 | 8 | To a stirred solution of 5.36 g (22.5 mmol) 14a and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 8 h at 60° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residu... | COC(=O)c1ccc(N(C)C)c(OC(F)(F)F)c1 | null | 69 | null |
575,630 | ord_dataset-f4512fe8cd804ac79da66cbc0c2b9d42 | null | 2002-01-01T00:12:00 | true | [CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][CH2:14][C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=2)[CH:7]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:1... | COC(=O)CCc1cccc(CNCc2cc3ccccc3o2)c1 | O=S(=O)(Cl)c1ccccc1 | null | null | null | 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 | The title compound of Step B was prepared following the method describe in Step B of Example 1 from 3-(3-{[(benzofuran-2-ylmethyl)-amino]-methyl}-phenyl)-propionic acid methyl ester of Step A and benzenesulfonyl chloride using triethylamine in place of N,N-diisopropylethylamine. 1H NMR (400 MHz, CDCl3) δ 7.83 (m, 2H), ... | COC(=O)CCc1cccc(CN(Cc2cc3ccccc3o2)S(=O)(=O)c2ccccc2)c1 | null | null | null |
1,324,935 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]3[N:39]=[C:24]4[C:25]([C:29]5[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=5)=[CH:26][CH:27]=[CH:28][N:23]4[N:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:38]... | CC(C)(C)OC(=O)N1CCN(c2cccc(Nc3nc4c(-c5ccc(S(C)(=O)=O)cc5)cccn4n3)c2)CC1 | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 6 | To a solution of 4-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (250.0 mg, 0.4556 mmol) in dichloromethane (1 mL) was added dropwise trifluoroacetic acid (0.40 mL, 5.2 mmol) and the mixture was stirred at room temperature for 6 hours. Th... | CS(=O)(=O)c1ccc(-c2cccn3nc(Nc4cccc(N5CCNCC5)c4)nc23)cc1 | null | null | null |
1,360,840 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]2[S:31][C:30]([S:32][CH3:33])=[N:29][CH:4]2[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:13]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[O:8][C:7]2=[O:28].[CH:34]1([CH2:37][NH2:38])[CH2:36][CH2:35]1>>[CH:34]1([CH2:37][NH:38][C:7]([C:6]2[C:1... | CSC1=NC2C=c3c(nc(-c4cc(C(F)(F)F)nn4-c4ncccc4Cl)oc3=O)=C(Cl)C2S1 | NCC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | See step f) of example H2 using 4-chloro-6-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-2-methylsulfanyl-3a,9a-dihydro-7-oxa-3-thia-1,5-diaza-cyclopenta[b]naphthalen-8-one as starting material and cyclopropanemethylamine. After overnight reaction and chromatography column purification, the expected pro... | CSC1=NC2C=C(C(=O)NCC3CC3)C(NC(=O)c3cc(C(F)(F)F)nn3-c3ncccc3Cl)=C(Cl)C2S1 | null | null | null |
1,349,629 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH3:1][NH:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[C:8]([Cl:13])[S:7][C:6]=1[Cl:14])=[O:4].[H][H]>C(O)C.[Ni]>[CH3:1][NH:2][C:3]([C:5]1[C:9]([NH2:10])=[C:8]([Cl:13])[S:7][C:6]=1[Cl:14])=[O:4] | CNC(=O)c1c(Cl)sc(Cl)c1[N+](=O)[O-] | [H][H] | null | [Ni] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2,5-dichloro-4-nitro-thiophene-3-carboxylic acid methylamide (565 mg) and Raney Ni (50 mg) in ethanol was stirred under 1 atm hydrogen for 5 hours. The reaction mixture was filtered and concentrated to afford 510 mg of 4-amino-2,5-dichloro-thiophene-3-carboxylic acid methylamide: 1H NMR (300 MHz, CDCl3) δ ... | CNC(=O)c1c(Cl)sc(Cl)c1N | null | 102.3 | null |
1,467,089 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[N:8]=[CH:7][C:6]=2[C:5]([CH3:16])=[CH:4]1)[CH3:2].[OH-].[Na+]>C1COCC1>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[N:8]=[CH:7][C:6]=2[C:5]([CH3:16])=[CH:4]1)[CH3:2] | CCn1cc(C)c2cnc(C(=O)OC)cc21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 3 | In a 200-ml round bottom flask, methyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1N, 6.0 g, 28 mmol) was dissolved in THF (50 ml). To the mixture was added a 2M NaOH (28 ml, 55 mmol) solution. The reaction was stirred at room temperature for 3 hrs. After completion, volatiles were removed and the residu... | CCn1cc(C)c2cnc(C(=O)O)cc21 | null | null | null |
1,392,087 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:23][C:24](=O)[C:25]#[C:26][CH2:27][S:28][CH2:29][CH3:30])C>C(O)(C)(C)C>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]4=[N:18][C:24](=[O:23]... | NC1=NC[C@@H](COc2ccc(C3CCCCC3)cc2)O1 | CCOC(=O)C#CCSCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)(C)O | null | null | null | null | null | null | null | null | null | null | 170 | null | To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.5 g, 1.82 mmol) in t-butanol (5 mL) was added 4-ethylsulfanyl-but-2-ynoic acid ethyl ester (0.411 g, 2.39 mmol). The reaction mixture was heated in a microwave oven at 170° C. for 20 min. The solvent was removed under vacuum, and the re... | CCSCc1cc(=O)nc2n1C[C@@H](COc1ccc(C3CCCCC3)cc1)O2 | null | 57.1 | null |
131,839 | ord_dataset-232d09663ed349c2a1fb1f05d411eae0 | null | 1985-01-01T00:07:00 | true | [CH:1]1(N)[CH2:3][CH2:2]1.C(N(CC)CC)C.[N:12]1[C:19]([Cl:20])=[N:18][C:16](Cl)=[N:15][C:13]=1[Cl:14]>CC(C)=O>[CH:1]1([C:16]2[N:18]=[C:19]([Cl:20])[N:12]=[C:13]([Cl:14])[N:15]=2)[CH2:2][CH2:3]1 | Clc1nc(Cl)nc(Cl)n1 | NC1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(C)=O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 28.5 g of cyclopropylamine and 50.5 g of triethylamine was added drop-by-drop to a stirred solution of 92.3 g of cyanuric chloride in 1.5 liters of dry acetone at room temperature. Then the acetone was evaporated and the residue was treated with a 1:1 v:v mixture of ice water and ether. The ether phase was... | Clc1nc(Cl)nc(C2CC2)n1 | null | null | null |
130,589 | ord_dataset-2f37329a4b254471a74f2eb0981f11ec | null | 1985-01-01T00:05:00 | true | P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([O:19][CH:20]=[CH:21][CH2:22]2)[CH:8]=[O:9])=[CH:16][CH:17]=1 | CN(C)C=O | Brc1ccc(-c2ccco2)cc1 | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 1 | (Vilsmeir procedure) Phosphorous oxychloride POCL3 (12.5 g) and Dimethyl formamide (7 ml) were added to a mixture of 2(4-bromophenyl)furan (20.4 g) in chlorobenzene (100 ml). The mixture was stirred at 10° for one hour. A further addition of POCl3 (1.5 g) and DMF (0.7 g) was then made and the reaction stirred for a fur... | O=CC1(c2ccc(Br)cc2)CC=CO1 | null | null | null |
512,388 | ord_dataset-85c00026681b46f89ef8634d2b8618c3 | null | 2001-01-01T00:07:00 | true | C1(CCCC2CCN([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:33][CH:34]4[CH2:37][CH2:36][CH2:35]4)[C:30]([OH:32])=[O:31])[CH2:18]3)CC2)C=CC=CC=1.[F:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=1[CH2:46][CH2:47][CH2:48][CH:49]1[CH2:54][CH2:53][NH:52]... | O=C(O)[C@@H](CC1CCC1)N1C[C@H](CN2CCC(CCCc3ccccc3)CC2)[C@@H](c2cccc(F)c2)C1 | Fc1cccc(F)c1CCCC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 26, Step A) and 4-(3-(2,6-difluorophenyl)propyl) piperidine.HCl (from EXAMPLE 114, Step A) using procedures analogous to those described in EXAMPLE 1, Steps J and K to... | O=C(O)[C@@H](CC1CCC1)N1C[C@H](CN2CCC(CCCc3c(F)cccc3F)CC2)[C@@H](c2cccc(F)c2)C1 | null | null | null |
488,605 | ord_dataset-37b0416f244344a08cf357e851eedf2a | null | 2001-01-01T00:01:00 | true | [CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([NH:9][C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:2][CH3:1])[CH2:12][CH2:13][CH3:14] | COc1ccccc1N | CCCCBr | 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 | null | null | A suspension of 6.2 g (50 mmol) o-anisidine M10, 7.5 g (55 mmiol) 1-bromobutane M17, 7.6 g (55 mmol) K2CO3 and 0.91 g (5.5 mmol) KI in 25 ml DMF was heated at 95° C. for 24 hours. DMF was evaporated and the residue was dissolved in 100 ml CHCl3 and 100 ml saturated NaCl. The organic layer was dried over Na2SO4. The sol... | CCCCNc1ccccc1OC | null | 53.6 | null |
1,355,718 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1([C:13]([OH:15])=[O:14])[C:10]([OH:12])=[O:11].F[C:17](F)(F)[C:18](O)=O>C(Cl)Cl>[CH2:17]([O:11][C:10]([C:2]1([C:13]([OH:15])=[O:14])[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:12])[CH3:18] | O=C(O)C1(C(=O)O)Cc2ccccc2C1 | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 20 | A 200 mL round bottom flask is charged with indan-2,2-dicarboxylic acid tent-butyl ester ethyl ester (8.69 g, 29.93 mmol). DCM (40 mL) and a stirring bar are added. Stirring is initiated. Trifluoroacetic acid (20.0 mL, 269 mmol) is added. After 20 h, tlc analysis (silica, 1:1 ethyl actetate:heptanes), indicates complet... | CCOC(=O)C1(C(=O)O)Cc2ccccc2C1 | null | null | null |
904,003 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | N[C:2]1[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[I-:16].[Cs+].N(OCCC(C)C)=O>C(Cl)Cl.[Cu]I>[I:16][C:2]1[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1 | [I-] | Nc1cc(C(F)(F)F)cc2[nH]c(=O)[nH]c12 | null | [Cu]I | CC(C)CCON=O | [Cs+] | 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 | 60 | 3 | (Analogous to the procedure described in Heterocycles, 2001, 55, 461-464). To a solution of 4-amino-6-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one from step (a) above (0.76 g, 3.5 mmol) in 20 mL of DCM was added CsI (0.91 g, 3.5 mmol), 12 (0.44 g, 1.75 mmol), and CuI (0.2 g, 1.06 mmol). To the mixture was added ... | O=c1[nH]c2cc(C(F)(F)F)cc(I)c2[nH]1 | null | null | null |
22,975 | ord_dataset-19b9e29d593f4660ab77c07b459da9bb | null | 1977-01-01T00:04:00 | true | [H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([CH:25]([OH:31])[CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])[CH:24]=1)[C:18](OC)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CCOCC>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:22]=[C:23]([CH:25]([CH2:26][NH:27][CH:28](... | COC(=O)c1cc(OCc2ccccc2)cc(C(O)CNC(C)C)c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | null | null | To a suspension of LiAlH4 (4.57 g, 120 moles) in anhydrous Et2O (0.5 l.) was added an ethereal solution (0.5 l.) of the methyl 3-benzyloxy-5-[2(isopropylamino)-1-hydroxyethyl]-benzoate (17.5 g, 50.9 mmoles) slowly at room temperature. The resultant mixture was heated at reflux for 4 hrs. The LiAlH4 and complex was hydr... | CC(C)NCC(O)c1cc(CO)cc(OCc2ccccc2)c1 | null | null | null |
190,822 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | [C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:23][CH2:24][N:25]1C(=O)C2=CC=CC=C2C1=O)[CH2:10][CH2:11][N:12]1C(=O)C2=CC=CC=C2C1=O)#[N:2].NN>CO>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:23][CH2:24][NH2:25])[CH2:10][CH2:11][NH2:12])#[N:2] | N#CCCCCCCN(CCN1C(=O)c2ccccc2C1=O)CCN1C(=O)c2ccccc2C1=O | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | A solution of (6-cyanohexyl)bis(2-phthalimidoethyl)amine (13.8g, 0.029 mol) and hydrazine (2.15g, 0.067 mol) in methanol (150 ml) was refluxed for 1.5 hours and allowed to stand overnight. The solvent was removed under reduced pressure and the residue was taken up in water (200 ml) and brought to pH≈2 with HC1. The pre... | N#CCCCCCCN(CCN)CCN | null | null | null |
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