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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
460,525 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [CH3:1][C:2]1[C:3]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][NH:30][CH3:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].C(N(CC)CC)C.[C:39]([CH2:43][C:44](Cl)=[O:45])([CH3:42])([CH3:41])[CH3:40].OS([O-])(=O)=O.[Na+... | CC(C)(C)CC(=O)Cl | CNCc1cc(-c2ncco2)ccc1-c1ccccc1S(=O)(=O)Nc1noc(C)c1C | null | O=S(=O)([O-])O | [Na+] | 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 | null | 0.08 | To the title product of Step F in 300 ml of CH2Cl2 at 0° C., triethylamine (6.17 g, 60.96 mmol) was added and stirred for 5 minutes. To the mixture, t-butylacetyl chloride (3.98 g, 29.57 mmol) was added dropwise over 10 minutes. The reaction mixture was stirred at 0° C. for 10 minutes and at room temperature for 1 hr. ... | Cc1onc(NS(=O)(=O)c2ccccc2-c2ccc(-c3ncco3)cc2CN(C)C(=O)CC(C)(C)C)c1C | null | null | null |
1,455,213 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [F:1][C:2]1[CH:3]=[C:4]([NH:9]/[C:10](/SC)=[CH:11]/[C:12]([C:14]2[CH:23]=[CH:22][C:17]3[O:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH2:26]([O:28][C:29](=[O:33])[CH2:30][NH:31][NH2:32])[CH3:27].Cl.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[CH2:26]([O:28][C:29](=[O:33])[CH2:30][N:31]1[C:12]([C:1... | CS/C(=C\C(=O)c1ccc2c(c1)OCCO2)Nc1ccc(F)c(F)c1 | CCOC(=O)CNN | null | Cl | O=C([O-])[O-] | [K+] | 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 | null | null | A mixture of D16 (0.00138 mol), 2-hydrazinyl-acetic acid ethyl ester.monohydrochloride (1:1) (0.00276 mol) and K2CO3 (0.00206 mol) in t-BuOH (100 ml) was stirred at 85° C. overnight in a sealed reaction vessel. The reaction mixture was cooled, filtered and the filtrate's solvent evaporated in vacuo. Yield: 0.55 g of E1... | CCOC(=O)Cn1nc(Nc2ccc(F)c(F)c2)cc1-c1ccc2c(c1)OCCO2 | null | null | null |
1,188,063 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [OH:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][C:15]([CH3:19])=[CH:16][CH:17]=O.N1C=CC=CC=1>>[OH:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]2[C:9]=1[CH:17]=[CH:16][C:15]([CH3:19])([CH3:14])[O:10]2 | O=Cc1cc([N+](=O)[O-])c(O)cc1O | CC(C)=CC=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 18 | A solution of 2,4-dihydroxy-5-nitro-benzaldehyde (10.61 g, 58 mmol) in Me2CO (6 mL) is added during a 5.5 h period to a stirring solution of 3-methyl-but-2-enal (4.00 g, 29 mmol) in pyridine (2.29 g, 2.34 mL, 29 mmol) at 120° C. After completion of addition heating is continued for an additional 18 h. The Me2CO is evap... | CC1(C)C=Cc2c(O)c(C=O)cc([N+](=O)[O-])c2O1 | null | null | null |
287,501 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [OH-:1].[Na+].Cl.[NH2:4][CH2:5][CH:6]([S:10][C:11](CC1C=CC=CC=1)=S)[C:7]([OH:9])=[O:8].Cl>C(O)C>[O:1]=[C:11]1[NH:4][CH2:5][CH:6]([C:7]([OH:9])=[O:8])[S:10]1 | NCC(SC(=S)Cc1ccccc1)C(=O)O | [OH-] | null | Cl | [Na+] | 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 | 0.5 | 12.0 ml of a 1 N aqueous solution of sodium hydroxide were added to a suspension of 1.2 g of 3-amino-2-(benzylthiocarbonylthio)propionic acid hydrochloride in 35 ml of ethanol, and the resulting mixture was stirred at room temperature for 30 minutes, after which 12.0 ml of 1 N aqueous hydrochloric acid were added, whil... | O=C1NCC(C(=O)O)S1 | null | null | null |
742,019 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]2[O:10][CH:9]([C:11]([F:13])([F:12])[F:14])[C:... | CCOC(=O)C1=Cc2cc(Cl)cc(-c3ccccc3)c2OC1C(F)(F)F | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 18 | A solution of the ester from step 1 (1.0 g, 2.6 mmol) was dissolved in THF (5 mL) and methanol (5 mL) was treated with a 2.5 N NaOH solution (4.0 mL, 10.4 mmol). The resulting mixture was stirred at room temperature for 18 hours. The solvent was removed in vacuo, and the residue taken up in ethyl acetate and acidified ... | O=C(O)C1=Cc2cc(Cl)cc(-c3ccccc3)c2OC1C(F)(F)F | null | 45.5 | null |
321,454 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | [NH2:1][CH2:2][C:3]([N:5]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:4].[CH3:22][C:23]1[CH:24]=[C:25]([N:29]=[C:30]=[O:31])[CH:26]=[CH:27][CH:28]=1>>[CH3:13][O:12][C:8]1[CH:7]=[C:6]([N:5]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[C... | Cc1cccc(N=C=O)c1 | COc1cccc(N(CC(=O)OC(C)(C)C)C(=O)CN)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 procedure used is similar to that described in Example 1, but starting with tert-butyl 2-[2-amino-N-(3-methoxyphenyl)acetamido]acetate (2.3 g) and 3-methylphenyl isocyanate (1.1 g). The product obtained is purified by chromatography on silica (0.04-0.063 mm) (150 g) contained in a column 3.5 cm in diameter [eluent:... | COc1cccc(N(CC(=O)OC(C)(C)C)C(=O)CNC(=O)Nc2cccc(C)c2)c1 | null | 65.9 | null |
1,456,653 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.[CH:19]1([CH:22]=O)[CH2:21][CH2:20]1.CCN(CC)CC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10](... | O=CC1CC1 | C[C@H]1COCCN1c1nc(Cl)nc2c1CNC2 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CC(Cl)Cl | null | null | null | null | null | null | null | null | null | 20 | 0.75 | To a stirring solution of (S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride (intermediate 6) (870 mg, 3.01 mmol) in dichloroethane, was added cyclopropanecarboxaldehyde (450 uL, 6.02 mmol) and Et3N (840 uL, 6.02 mmol). The reaction mixture was stirred at room temperature (20°... | C[C@H]1COCCN1c1nc(Cl)nc2c1CN(CC1CC1)C2 | null | 94.9 | null |
1,588,537 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[C:22]([CH3:24])[C:18]([C:19](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[OH:14][C:13]1[N:12]([C:15]2[CH:23]=[C:22]([CH3:24])[C:18]([C:19]([N:29]3[CH2:30][CH2:31][N:26... | CN1CCNCC1 | Cc1cc(-n2ncc(-c3ccc(C#N)cc3)c2O)ncc1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner similar to Example 412 using 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)-4-methylnicotinic acid and 1-methylpiperazine. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39 (s, 3 H) 2.82 (s, 3 H) 4.02 (br. s., 4 H) 4.56 (br. s., 4 H) 7.79 (d, J=8.59 Hz, 2 H) 8.12 (br. s., 2 H) 8.37 (s, 1... | Cc1cc(-n2ncc(-c3ccc(C#N)cc3)c2O)ncc1C(=O)N1CCN(C)CC1 | null | null | null |
1,117,009 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [C:1]([NH:4]/[C:5](=[CH:9]\[CH2:10][PH:11]([CH2:13][OH:14])=[O:12])/[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[H][H]>CO>[C:1]([NH:4][C@@H:5]([CH2:9][CH2:10][PH:11]([CH2:13][OH:14])=[O:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2] | CC(=O)N/C(=C\C[PH](=O)CO)C(=O)O | [H][H] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 5 | (Z)-2-acetylamino-4-hydroxymethylphosphinyl-2-butenoic acid (4.0 g, 18 mmol), (RuCl(p-cymene)((S)-binap)Cl (8.4 mg, 0.009 mmol), and methanol (20 ml) were added to a 200 ml autoclave, and a nitrogen substitution and a hydrogen substitution were performed. The temperature in the autoclave was set to 70° C., hydrogen gas... | CC(=O)N[C@@H](CC[PH](=O)CO)C(=O)O | null | 612.4 | null |
1,662,328 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>>[F:1][C:2]1[CH:16]=[CH:15][C:5](/[C:6](/[Cl:19])=[N:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1 | O=C(Nc1ccccc1)c1ccc(F)cc1 | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Into a 500-mL 3-necked round-bottom flask, was placed 4-fluoro-N-phenylbenzamide (50 g; 233 mmol) and thionyl chloride (200 mL). The mixture was stirred at refluxed for 3 h and then the solvent was evaporated to dryness to afford (Z)-4-fluoro-N-phenylbenzimidoyl chloride as white solid. The solid was dissolved into chl... | Fc1ccc(/C(Cl)=N/c2ccccc2)cc1 | null | null | null |
1,008,666 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | COC1C=CC(C[O:10][C:11]2[N:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]([CH2:33][C:34]([F:37])([F:36])[F:35])[C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=3)=[CH:13][CH:12]=2)=CC=1>[Pd]>[O:10]=[C:11]1[NH:16][CH:15]=[C:14]([O:17][CH2:18][CH2:19][N:20]([CH2:33][C:34]([F:37])([F:... | COc1ccc(COc2ccc(OCCN(CC(F)(F)F)c3ccc(C#N)c(C(F)(F)F)c3)cn2)cc1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.75 | A mixture of 4-[(2-{[6-({[4-(methyloxy)phenyl]methyl}oxy)-3-pyridinyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.270 g, 0.51 mmol; step C above) and Pd—C (0.027 g of 10 wt % on activated carbon (dry basis), ca. 50 wt % H2O, ca. 0.013 mmol Pd) was stirred under an atmosphere of H2 for 45 m... | N#Cc1ccc(N(CCOc2ccc(=O)[nH]c2)CC(F)(F)F)cc1C(F)(F)F | null | 77.4 | null |
1,667,160 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Br[C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[Cu](C#N)[C:15]#[N:16]>CN1CCCC1=O.CCOC(C)=O.Cl>[C:10]([C:4]1[C:3]([OH:13])=[C:2]([C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)[C:15]#[N:16])(=[O:12])[CH3:11] | CC(=O)c1cc(Cl)c(C)c(Br)c1O | N#C[Cu]C#N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | 200 | null | A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (4.85 g, 18.4 mmol) and copper cyanide (2.47 g, 27.6 mmol) in N-methylpyrrolidinone (15 mL) was heated at 200° C. for 1 h. After cooled to rt, the mixture was diluted with EtOAc and 1 N HCl. The layers were separated and the aqueous layer was extracted ... | CC(=O)c1cc(Cl)c(C)c(C#N)c1O | null | null | null |
1,232,268 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:3]\[C:4](OCC)=[O:5].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:3]\[CH2:4][OH:5] | CCCCCCCCCC/C(C)=C/C(=O)OCC | 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 | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | -78 | null | Compound E (0.19 mmol) was dissolved in anhydrous toluene (3 mL) and chilled to −78° C. DIBAL-H (0.585 mmol, 2.0 M in toluene) was added dropwise. The solution reacted for 45 minutes and was warmed slightly. The reaction was quenched with 10% aqueous sodium potassium tartrate. The layers were separated and the aqueous ... | CCCCCCCCCC/C(C)=C/CO | null | null | null |
1,270,461 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([Li])CCC.Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:7][N:6]=1 | BrCCCc1ccccc1 | COc1ccc(Br)cn1 | 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 | -78 | 0.5 | According to Scheme 22 Method A: To a solution of 5-bromo-2-methoxypyridine (1 eq, 2.70 mmol, 0.50 g) in THF (4.4 mL) at −78° C. under nitrogen was added dropwise n-butyl lithium (1 eq, 2.5M in hexanes, 2.70 mmol, 1.10 mL). The reaction mixture was stirred at −78° C. for 30 min. and 1-(3-bromopropyl)benzene (1 eq, 2.70... | COc1ccc(CCCc2ccccc2)cn1 | null | 17 | null |
1,391,923 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]2[C:18]=1[CH2:19][CH2:20][C@H:21]2[O:27][C:28]1[CH:41]=[CH:40][C:31]2[C@H:32]([CH2:35][C:36]([O:38]C)=[O:37])[CH2:33][O:34][C:30]=2[CH:29]=1.[OH-].[Na+]>C(O)C>[C... | COC(=O)C[C@@H]1COc2cc(O[C@@H]3CCc4c(-c5c(C)cc(OCCCS(C)(=O)=O)cc5C)ccc(F)c43)ccc21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | 1 | Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(3-(methylsulfonyl)propoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (Intermediate 29; 9 mg) is suspended in ethanol (1 mL) and aqueous NaOH (1 M; 0.2 mL) is added. The mixture is stirred for 1 hour then concentrated under vacuum, acidified ... | Cc1cc(OCCCS(C)(=O)=O)cc(C)c1-c1ccc(F)c2c1CC[C@H]2Oc1ccc2c(c1)OC[C@H]2CC(=O)O | null | 96.8 | null |
1,476,864 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH:1]1([C:4]2[CH:5]=[CH:6][C:7](/[C:12](/[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)=[CH:13]/[C@@H:14]3[NH:18][C:17](=[O:19])[CH2:16][CH2:15]3)=[N:8][C:9]=2[O:10][CH3:11])[CH2:3][CH2:2]1.[H][H]>CO.[Br-].[Zn+2].[Br-].[Pd]>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:12]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])... | [H][H] | COc1nc(/C(=C/[C@H]2CCC(=O)N2)c2ccc(Cl)c(Cl)c2)ccc1C1CC1 | null | [Pd] | [Br-] | [Zn+2] | 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 | Zinc bromide (20 mg) and 10% palladium-activated carbon (40 mg) were added to a solution of (5R)-5-[(E)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(3,4-dichlorophenyl)ethenyl]pyrrolidin-2-one (100 mg) in methanol (3 mL), and the mixture was stirred at room temperature for 18 hours in a hydrogen atmosphere. The reaction ... | COc1nc(C(C[C@H]2CCC(=O)N2)c2ccc(Cl)c(Cl)c2)ccc1C1CC1 | null | null | null |
1,323,361 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[CH2:2][C@@:3]([OH:17])([CH3:16])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([CH3:15])[CH:8]=1)=[O:5].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4]([C@@:3]2([CH3:16])[CH2:2][O:17]2)=[O:5])=[CH:8][C:9]=1[CH3:15])#[N:14] | Cc1cc(NC(=O)[C@@](C)(O)CBr)ccc1C#N | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | (2R)-3-Bromo-2-hydroxy-2-methyl-N-(4-cyano-3-methylphenyl)propion-amide (1.54 g, 5.2 mmol) was dissolved in 50 ml of toluene and stirred for 5 minutes with 15 ml of 1 M NaOH at room temperature. Organic layer was separated and washed with 2×25 ml of water. Toluene was filtered and evaporated to give 0.905 g of the prod... | Cc1cc(NC(=O)[C@@]2(C)CO2)ccc1C#N | null | 80.5 | null |
754,398 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [C:1]([O:5][C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:26]2[CH:22]([CH2:23][CH:24]([O:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][N:31]=3)[CH2:25]2)[C:21](=[O:40])[NH:20][C:19]2([C:41]([OH:43])=O)[CH:17]([CH2:18]2)[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[C... | CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(C(=O)O)NC(=O)C2CC(Oc3nccc4ccccc34)CN2C1=O | CCCC1(S(N)(=O)=O)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared from 14-tert-butoxycarbonylamino-18-(isoquinolin-1-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]-nonadec-7-ene-4-carboxylic acid (50 mg, 0.075 mmol) and 1-propyl-cyclopropanesulfonic acid amide (16 mg, 0.098 mmol, prepared as described above) to give [18-(isoquinolin-1-yloxy)-2,15-dioxo-4-(1-propyl-cyclop... | CCCC1(S(=O)(=O)NC(=O)C23CC2C=CCCCCCC(NC(=O)OC(C)(C)C)C(=O)N2CC(Oc4nccc5ccccc45)CC2C(=O)N3)CC1 | null | null | null |
1,182,815 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])=[C:12]([CH:20]([CH3:22])[CH3:21])[N:11]=[C:10]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[C:12]([CH:20]... | COC(=O)/C=C/c1c(-c2ccc(F)cc2)nc(N(C)S(C)(=O)=O)nc1C(C)C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of methyl 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl](2E)-propenoate (10 g) in ethanol (200 ml) was treated with aqueous sodium hydroxide solution (0.1N, 246 ml) at 0-5° C. The reaction mixture was stirred at 25-30° C. for 12 h for completion of hydrolysis and ethano... | CC(C)c1nc(N(C)S(C)(=O)=O)nc(-c2ccc(F)cc2)c1/C=C/C(=O)O | null | 97.4 | null |
143,788 | ord_dataset-1895fe091c3f47afa1ee96a41a250de4 | null | 1986-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[C:26]([F:27])[C:11]=3[S:10]2)=[CH:5][CH:4]=1.[ClH:28].[C:29](OC(=O)C)(=[O:31])[CH3:30]>>[ClH:28].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:29... | CC(=O)OC(C)=O | COc1ccc([C@@H]2Sc3c(F)cccc3N(CCN(C)C)C(=O)[C@@H]2O)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-9-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 10 ml of acetic anhydride is treated in the same manner as described in Example 54. The crude product is converted to its hydrochloride and recrystallized from a mixture of isopropa... | COc1ccc([C@@H]2Sc3c(F)cccc3N(CCN(C)C)C(=O)[C@@H]2OC(C)=O)cc1 | null | null | null |
930,246 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[CH:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1.[CH2:34]([CH2:36][NH2:37])[OH:35]>C1COCC1.CCOC(C)=O>[OH:35][CH2:34][CH2:36][NH:... | NCCO | Cc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2ccnc(-c3cccc(S(=O)(=O)Cl)c3)c2)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | null | The title compound was prepared from the solution of 3-[6-methyl-4-(4-trifluoromethylphenyl)-[2,4′]bipyridinyl-2′-yl]-benzenesulfonyl chloride (example 346 step 2) (ca. 0.2 g, 0.41 mmol) by treatment with excess ethanolamine in THF (5 mL) at 50° C. for 16 h. Cooled to rt, diluted with EtOAc, washed with 1 N HCl, dried ... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cc(-c2ccnc(-c3cccc(S(=O)(=O)NCCO)c3)c2)n1 | null | 21 | null |
44,917 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | Cl.Br[C:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:7])[CH2:4][CH2:5][NH2:6].CC(C)=[O:23]>O.S(=O)(=O)(O)O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:3]([OH:23])([CH3:7])[CH2:4][CH2:5][NH2:6])=[CH:9][CH:10]=2)=[CH:15][CH:16]=1 | CC(Br)(CCN)c1ccc(-c2ccc(F)cc2)cc1 | CC(C)=O | null | Cl | O=S(=O)(O)O | 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 | 3.59 g of 3-bromo-3-(4'-fluoro-4-biphenylyl)butylamine hydrochloride [obtainable by reacting 3-hydroxy-3-(4'-fluoro-4-biphenylyl)-butyramide with PBr3 to give 3-bromo-3-(4'-fluoro-4-biphenylyl)-butyramide and reduction with LiAlH4 ] are dissolved in a mixture of 15 ml of acetone and 15 ml of water, 1 drop of sulfuric a... | CC(O)(CCN)c1ccc(-c2ccc(F)cc2)cc1 | null | null | null |
1,274,494 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [I:1]I.[CH3:3][N:4]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([CH3:13])=[N:5]1>S(=O)(=O)(O)O>[I:1][C:7]1[C:6]([CH3:13])=[N:5][N:4]([CH3:3])[C:8]=1[C:9]([F:10])([F:11])[F:12] | Cc1cc(C(F)(F)F)n(C)n1 | II | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | 2 | Iodine (30 g) was dissolved in 60% sulfuric acid (fuming, 80 g), and 1,3-dimethyl-5-trifluoromethylpyrazole (13.12 g, 80 mmol) was slowly added under ice-cooling. The mixture was stirred at 0° C. for 2 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with... | Cc1nn(C)c(C(F)(F)F)c1I | null | 86.2 | null |
1,405,077 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [C:1]1([C:7]2[S:8][C:9]([C:18]([O:20]C)=O)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][OH:23].[OH-].[K+]>CO.C1COCC1>[OH:23][NH:22][C:18]([C:9]1[S:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)... | NO | COC(=O)c1sc(-c2ccccc2)nc1-c1ccccc1 | null | [K+] | [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 | 0 | 18 | A 100 mL round-bottomed flask was charged with methyl 2,4-diphenylthiazole-5-carboxylate 73 (420 mg, 1.422 mmol) in MeOH (2.844 ml) and THF (2.84 ml) and the solution was cooled down to 0° C. Then a 50% aqueous solution of hydroxylamine (4697 mg, 71.1 mmol) and 4M potassium hydroxide solution (0.427 ml, 1.706 mmol) wer... | O=C(NO)c1sc(-c2ccccc2)nc1-c1ccccc1 | null | 71.9 | null |
1,392,540 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3]CC)=[O:2].[F:26][C:27]([F:43])([F:42])[C:28]([NH:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH2:39][CH2:40][CH3:41])=O>C1(C)C=CC=CC=1>[F:26][C:27]([F:43])([F:42])[C:28]([NH:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH2:39][... | CCCOc1ccc(F)cc1NC(=O)C(F)(F)F | CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Carboethoxymethylene triphenylphosphorane (41.52 g, 119.2 mmol) was added to a toluene solution (100 ml) of 2,2,2-trifluoro-N-(5-fluoro-2-propoxyphenyl)acetamide (15.83 g, 59.1 mmol). The mixture was stirred under a nitrogen atmosphere while heating under reflux for 4 hours. The reaction mixture was cooled to room temp... | CCCOc1ccc(F)cc1NC(=CC(=O)O)C(F)(F)F | null | 99 | null |
1,087,031 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[C@@H:10]([C@@H:21]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H... | C[C@H](Oc1ccc(C#N)cn1)[C@H]1CN(Cc2ccccc2)C[C@@H]1c1ccc(Cl)c(F)c1 | null | null | CC(Cl)OC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | 100 | null | To a solution of 6-{(S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile—100 mg (0.23 mmol) dissolved in toluene (2 mL) were added 98 mg (0.69 mmol) of 1-chloroethyl chloroformate and 89 mg (0.69 mmol) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. Aft... | C[C@H](Oc1ccc(C#N)cn1)[C@H]1CNC[C@@H]1c1ccc(Cl)c(F)c1 | null | 75.4 | null |
1,315,867 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:4].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:15][C:13]1[CH:12]=[C:7]([CH:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9] | CNC(=O)c1cc(C(=O)OC)cc([N+](=O)[O-])c1 | null | null | [Pd] | O=C[O-] | [NH4+] | 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 | 40 | null | To a solution of methyl 3-[(methylamino)carbonyl]-5-nitrobenzoate (Intermediate 29) (1.33 g, 5.59 mmol), in ethanol (30 mL) were added ammonium formiate (3.52 g, leg.) and Pd/C (catalytic quantity). The reaction was stirred at 40° C. for one night. After filtration on celite, the solvent was evaporated in vacuo. The re... | CNC(=O)c1cc(N)cc(C(=O)OC)c1 | null | 48.1 | null |
1,282,944 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([NH2:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=O>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:12]=[C:7]3[C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:10]=4[NH:9][N:8]3[CH:14]=2)=[CH:18][CH:19]=1 | COc1ccc2c(N)n[nH]c2c1 | O=C(CBr)c1ccc(F)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 2-(4-fluorophenyl)-7-methoxy-5H-imidazo[1,2-b]indazole (W289) was prepared using the general procedure for cyclization between 6-methoxy-1H-indazol-3-amine (80 mg, 0.5 mmol) and 2-bromo-1-(4-fluorophenyl)ethanone (119 mg, 0.55 mmol), as an off-white solid (30 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 1 H)... | COc1ccc2c(c1)[nH]n1cc(-c3ccc(F)cc3)nc21 | null | null | null |
852,402 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[Br:13][CH2:14][CH2:15]Br.O>CN(C=O)C>[Br:13][CH2:14][CH2:15][NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1 | CC(=O)c1ccc(N)cc1 | BrCCBr | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | To a suspension of 60% NaH (5.93 g, 247.08 mmol) in DMF (80 mL) taken in a one liter 2 neck round bottom flask fitted with a pressure equalizing addition funnel and a septum was added a solution of p-aminoacetophenone (20 g, 148.1 mmol) in DMF (60 mL) in drops through the pressure equalizing addition funnel under nitro... | CC(=O)c1ccc(NCCBr)cc1 | null | 14.2 | null |
1,539,601 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[N:33]1[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[N:35][CH:34]=1>>[F:1][C:2]1[CH:11]=... | O=C(O)c1ccncn1 | Cc1c(N2CCNCC2)nc2cc(F)cc(F)c2c1Nc1cncc(N2CCOCC2)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 | Prepared according to Procedure Q using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (40.0 mg, 0.09 mmol) and pyrimidine-4-carboxylic acid to give (4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazin-1-yl)(pyrimidin-4-yl)methanone. 1H NMR (DMSO-d6) ... | Cc1c(N2CCN(C(=O)c3ccncn3)CC2)nc2cc(F)cc(F)c2c1Nc1cncc(N2CCOCC2)c1 | null | null | null |
93,039 | ord_dataset-f0d0fe3f599c471ca1c011dbbcdeeff2 | null | 1982-01-01T00:04:00 | true | [CH3:1][N:2]([CH2:4][CH2:5][NH2:6])[CH3:3].[C:7]1([N:13]=[C:14]=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[C:7]1([NH:13][C:14]([NH:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1 | CN(C)CCN | O=C=Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 88 g of dimethylaminoethylamine are dissolved in 500 ml of toluene and then 119 g of phenyl isocyanate are added dropwise in the course of 10 minutes, whereupon the temperature rises to 97° C. The mixture is refluxed for 4 hours. On cooling, the product crystallises and is filtered with suction. The moist product is re... | CN(C)CCNC(=O)Nc1ccccc1 | null | null | null |
1,422,787 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [NH2:1][C@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[H-].[Na+].O=[CH:13][CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[C:24]([O:26][CH3:27])=[O:25])[CH:17]=[CH:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[C@H:2]([NH:1][CH2:13][CH2:... | COC(=O)c1cccc2ccn(CC=O)c12 | N[C@@H]1CN2CCC1CC2 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | null | 1 | To a stirred suspension of (S)-(−)-3-aminoquinuclidine (1.4 g, 7.0 mmol) in methylene chloride (50 mL) was added sodium hydride (562 mg, 14.0 mmol) in portions and the mixture was stirred for 1 h. Acetic acid (0.6 mL) was added dropwise, followed by methyl 1-(2-oxoethyl)-1H-indole-7-carboxylate (1.3 g, 5.9 mmol) from S... | COC(=O)c1cccc2ccn(CCN[C@@H]3CN4CCC3CC4)c12 | null | 72 | null |
1,422,008 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | Cl[S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:16][C:15]([C:23]([F:26])([F:25])[F:24])=[N:14]1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][C:20]([S:2]([OH:5])(=[O... | FC(F)(F)c1cc(-c2cccs2)n(-c2ccccc2Cl)n1 | O=S(=O)(O)Cl | null | O=S(=O)([O-])[O-] | [Na+] | 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 | null | Chlorosulfonic acid (1.0 mL, 15 mmol) was added dropwise to a cold (−78° C.) solution of 1-(2-chlorophenyl)-5-(thiophen-2-yl)-3-(trifluoromethyl)-1H-pyrazole (1.0 g, 3.2 mmol) in CH2Cl2 (22 mL) After 75 minutes stirring at −78° C. the cooling bath was removed and the brown solution was allowed to warm to ambient temper... | O=S(=O)(O)c1ccc(-c2cc(C(F)(F)F)nn2-c2ccccc2Cl)s1 | null | null | null |
1,243,135 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([F:12])([F:11])[F:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27])([CH3:22])[CH3:21])#[N:19]>O1CCCC1>[C:18]([C:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]... | CC(C)(C#N)c1cccc(C(=O)Cl)c1 | Nc1ccc(C(F)(F)F)c(O)c1 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | To a two-layer solution of 5-amino-2-(trifluoromethyl)phenol (1.50 g, 8.46 mmol) in tetrahydrofuran (25 mL)/1N aqueous sodium hydrogen carbonate solution (25 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (15 mL), and the mixture was stirred at room temperatur... | CC(C)(C#N)c1cccc(C(=O)Nc2ccc(C(F)(F)F)c(O)c2)c1 | null | 69 | null |
478,119 | ord_dataset-21c1b1c06c7e4e09a38b5b1c71a32e52 | null | 2000-01-01T00:10:00 | true | [CH:1]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[N+:9]([O-])=O)[C:4]([Cl:12])=[CH:3][CH:2]=1.[CH:13]1[CH2:17][CH:16]=[CH:15][CH:14]=1>>[Cl:12][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH:7]1[CH:15]2[CH2:16][CH:17]([CH:13]=[CH:14]2)[CH:8]1[NH2:9] | C1=CCC=C1 | O=[N+]([O-])/C=C/c1ccccc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This material (LC-MS m/z 220 (MH+)) was prepared via the nitro derivative according to the procedure described in Preparation 92 but starting instead with 2-chloro-omega-nitrostyrene and cyclopentadiene. | NC1C2C=CC(C2)C1c1ccccc1Cl | null | null | null |
196,693 | ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9 | null | 1989-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17]O)[N:7]=1)[CH3:2].CS([Cl:24])(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17][Cl:24])[N:7]=1)[CH3:2] | CS(=O)(=O)Cl | CCOC(=O)Cc1nn(CO)c(=O)c2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of ethyl-3-hydroxymethyl-4-oxo-3-H-phthalazin-1-ylacetate (1.31 g) and methanesulfonyl chloride (0.69 g) in methylene chloride (10 ml) containing pyridine (0.8 ml) was stirred at room temperature overnight. Upon evaporation of methylene chloride and purification of the residue by chromatography on silica gel... | CCOC(=O)Cc1nn(CCl)c(=O)c2ccccc12 | null | null | null |
344,031 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[C:9]1([NH:15][C:16](=[O:30])[NH:17][N:18]=[C:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.C(O)C>[N:2](=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[C:19]1=[N:18][NH:17][C:16]([NH:15][C:... | NO | O=C(NN=c1c(=O)c2ccccc2c1=O)Nc1ccccc1 | null | CC(=O)[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | 0.01 mol of hydroxylamine hydrochloride and 0.01 mol sodium acetate in solution in 20 ml water were added to a solution of 0.01 mol of 2-(4-phenyl semicarbazono)-indan-1,3-dione in 150 ml ethanol. The reaction mixture was refluxed for 1 hour, then the ethanol was eliminated at reduced pressure. The resulting crystals w... | O=C(NN=c1c(=O)c2ccccc2c1=NO)Nc1ccccc1 | null | null | null |
214,733 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [OH:1][CH:2]1[CH:6]([CH2:7][NH2:8])[CH2:5][N:4](CC2C=CC=CC=2)[CH2:3]1.[ClH:16]>CO.C(O)C.[Pd]>[ClH:16].[ClH:16].[OH:1][CH:2]1[CH:6]([CH2:7][NH2:8])[CH2:5][NH:4][CH2:3]1 | NCC1CN(Cc2ccccc2)CC1O | null | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CO | null | null | null | null | null | null | null | null | null | null | null | A solution of 2.19 g (10.6 mmol) of 3-hydroxy-4-aminomethyl-1-phenylmethyl pyrrolidine in 60 ml anhydrous methanol and 5.3 ml 5N hydrochloric acid in ethanol was hydrogenized over 1.83 g palladium on carbon for 17 hours. The catalyst was filtered off, the solvent removed to afford 1.39 g (70%) of title compound. | NCC1CNCC1O | null | 70 | null |
359,286 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[C:15]1([CH2:21][CH2:22][CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].CO>C(OCC)(=O)C>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])... | c1cc(OC[C@@H]2CO2)c2cc[nH]c2c1 | c1ccc(CCCC2CCNCC2)cc1 | null | O=C(O)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CO | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 4-(3-phenylpropyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 73% overall yield. FDMS m/e=392 (M+ of free base). α[D]589 =-13.... | O[C@H](COc1cccc2[nH]ccc12)CN1CCC(CCCc2ccccc2)CC1 | null | null | null |
1,650,717 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [C:1]([O:5][C:6]([N:8]1[C@H:14]([C:15](O)=[O:16])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][OH:16])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)OC(=O)N1[C@@H]2C[C@@H]2CC[C@H]1C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1CCOC1 | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of D5 (11 g, 45.6 mmol) in THF (350 mL) cooled at 0° C., BH3 1M in THF (90 mL, 90 mmol) was added and the mixture was stirred at room temperature for 2 hours. Methanol (50 mL) was added; this solution was concentrated and co-evaporated twice from methanol to give the title compound. Yield (11 g, 100%). | CC(C)(C)OC(=O)N1[C@H](CO)CC[C@H]2C[C@H]21 | null | null | null |
1,602,685 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].[F:23][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:27](=O)[CH2:28]Br>>[F:23][C:24]1[CH:25]=[C:26]([C:27]2[N:12]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:2])=[... | O=C(CBr)c1cc(F)cc(F)c1 | COC(=O)c1cc(C(N)=S)ccc1-c1ccccc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4-[4-(3,5-Difluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (38 mg, 14%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 3,5-difluorophenacyl bromide (available from SynQuest Laboratories, Inc.) using the pro... | O=C(O)c1cc(-c2nc(-c3cc(F)cc(F)c3)cs2)ccc1-c1ccccc1[N+](=O)[O-] | null | 14 | null |
1,203,718 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=2[CH:27]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[C:36]([O:38][CH3:39])=[O:37]>C([O-])(=O)C.[Cu+2].C([O-])(... | COC(=O)c1ccc(B(O)O)cc1F | CC(c1ccc(O)cc1Cl)C(O)(c1ccc2c(c1)N(C)C(=O)CO2)C(F)(F)F | null | [Cu+2] | CC(=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to Example 5, 6-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (Example 56, step 4) was reacted with 3-fluoro-4-methoxycarbonylphenylboronic acid, copper-(II)-acetate and pyridine to give the title compound as a white solid. MS (m/e, ISP neg. ion)=566.2 ... | COC(=O)c1ccc(Oc2ccc(C(C)C(O)(c3ccc4c(c3)N(C)C(=O)CO4)C(F)(F)F)c(Cl)c2)cc1F | null | null | null |
516,830 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7](=O)[C:6]=2[CH:11]=1.Cl.[NH:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])N>C(O)C.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[C:23]4[C:15](=[C:16]([C:17]([OH:19])=[O:18])[CH:20]=[CH:21][CH:22]=4)[NH:13][C:7]=3[C:6]=2[CH:11]=1 | NNc1ccccc1C(=O)O | O=C1COc2ccc(I)cc21 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 5-iodo-3(2H)-benzofuranone (0.551 g, 2.12 mmol) [Cagniant, P. et al. Hebd. Seances Acad. Sci., Ser. C, 1976, 282 (21), 993-6] in ethanol (100 mL) was added a solution of 2-hydrazinobenzoic acid hydrochloride (0.800 g, 4.24 mmol) in deionized water (50 mL). The mixture was stirred for one hour at room t... | O=C(O)c1cccc2c1[nH]c1c3cc(I)ccc3oc21 | null | 60 | null |
125,574 | ord_dataset-fd44e5eeeeb4473cb5fbff2d885d7833 | null | 1985-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:11])([CH3:10])[C:8]#[CH:9])[O:4][N:3]=1.[CH3:12][N:13]=[C:14]=[O:15]>O1CCCC1>[CH3:12][NH:13][C:14]([NH:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:11])([CH3:10])[C:8]#[CH:9])[O:4][N:3]=1)=[O:15] | CN=C=O | C#CC(C)(C)c1cc(N)no1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 7.5 g of 3C and 5 ml of methyl isocyanate in 50 ml of tetrahydrofuran was heated at 50°-60° C. for two days. The solvent was evaporated under reduced pressure and the residue was chromatographed over silica gel, using as eluent a 1:4:20 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane, to give 1... | C#CC(C)(C)c1cc(NC(=O)NC)no1 | null | null | null |
161,318 | ord_dataset-e402405fd21e4770a14f157cb62ca439 | null | 1987-01-01T00:07:00 | true | [C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[OH:16][CH:17]1[O:25][C@H:24]([CH2:26][OH:27])[C@@H:22]([OH:23])[C@H:20]([OH:21])[C@H:18]1[NH2:19].O>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([NH:19][C@@H:18]1[C@@H:20]([OH:21])[C@H:22]([OH:23])[C@@H:24]([CH2:26][OH:2... | N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O | CCCCCCCCCCCC(=O)Cl | null | Cl | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 55 g of dodecanoyl chloride were dissolved in 170 ml of tetrahydrofuran and added dropwise, with vigorous stirring, to a solution of 54 g of D-glucosamine hydrochloride in 330 ml of aqueous sodium carbonate solution (20%). After completion of the addition of the acid chloride, the mixture was stirred for a further hour... | CCCCCCCCCCCC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O | null | null | null |
1,636,108 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | C([O:3][C:4](=[O:35])[CH2:5][CH2:6][NH:7][C:8](=[O:34])[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:28]2[CH2:31][C:30]([CH3:33])([CH3:32])[CH2:29]2)[NH:16][C:17]2[C:26]([CH3:27])=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>O1CCCC1.CO>[CH3:32][C:30]1([CH3:33])[CH2:31][CH:... | CCOC(=O)CCNC(=O)c1ccc(C(Nc2nc3ccccc3cc2C)C2CC(C)(C)C2)cc1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | null | null | (+/−)-3-{4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid ethyl ester (Intermediate 27) (36 mg, 0.076 mmol) was dissolved in tetrahydrofuran (3 mL) and methanol (1 mL), and 1.0 M sodium hydroxide (2 mL) was added. This was stirred as a solution at room temperature for 45 m... | Cc1cc2ccccc2nc1NC(c1ccc(C(=O)NCCC(=O)O)cc1)C1CC(C)(C)C1 | null | 120.5 | null |
43,513 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | [C:1]([CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)#[N:2].S(Cl)([Cl:16])=O>>[C:1]([CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)#[N:2] | O=S(Cl)Cl | N#CCCc1ccc(C(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 17.5 parts of 4-(2-cyanoethyl) benzoic acid and 120 parts of thionyl chloride are refluxed for 15 minutes. The surplus thionyl chloride is then eliminated under reduced pressure and the 4-(2-cyanoethyl) benzoyl chloride is obtained which is liquid at atmospheric temperature. | N#CCCc1ccc(C(=O)Cl)cc1 | null | null | null |
1,317,860 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[CH:28]=[CH:27][C:17]([C:18]([NH:20][CH2:21][CH:22](OC)OC)=[O:19])=[C:16]([CH3:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH3:35][O:36][NH2:37]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[... | CON | COC(CNC(=O)c1ccc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)cc1C)OC | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | In a solution of 152 mg of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethoxyethyl)-2-methyl benzoic acid amide (Compound of the present invention No. 5-083) synthesized similarly to Synthetic Example 5 in 14 ml of methaol-water (6:1) mixed solvent, 38 mg of methoxyamine hydrochlorid... | CON=CCNC(=O)c1ccc(C2=NOC(c3cc(Cl)cc(Cl)c3)(C(F)(F)F)C2)cc1C | null | 69.4 | null |
1,309,708 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.[O:19]=[S:20]1(=[O:34])[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:22][CH2:21]1>>[O:34]=[S:20]1(=[O:19])[CH2:21][CH2:22][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C... | Nc1ccc(CN2CCS(=O)(=O)CC2)cc1 | CS(=O)c1ncc2ccc(-c3cccnc3)n2n1 | null | null | null | null | null | null | null | 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-(1,1-Dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-(7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine was prepared from 2-methanesulfinyl-7-pyridin-3-yl-pyrrolo[2,1-f][1,2,4]triazine and 4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenylamine in an analogous manner to Example 1049. Product isolated as an or... | O=S1(=O)CCN(Cc2ccc(Nc3ncc4ccc(-c5cccnc5)n4n3)cc2)CC1 | null | null | null |
515,721 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | Br[C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C>C(O)C.[Pd]>[C:8]1([C:5]2[N:4]=[C:3]([C:14]([OH:16])=[O:15])[CH:2]=[CH:7][N:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1 | O=C(O)c1nc(-c2ccccc2)ncc1Br | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A solution of 500 mg 5-bromo-2-phenyl-4-pyrimidinecarboxylic acid and 1 mL N,N-diisopropylethylamine in 5 mL of ethanol was hydrogenated at 40 psi of H2 for 16 hr using 200 mg of 10% palladium-on-carbon as catalyst. The catalyst was filtered off and the ethanol removed by evaporation under reduced pressure. The residue... | O=C(O)c1ccnc(-c2ccccc2)n1 | null | 83.6 | null |
1,741,524 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [CH2:1]([N:3]([CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)[C:4]1[C:5]([CH3:17])=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])[CH3:2].Cl.[NH2:26][CH2:27][C:28]1[C:29](=[O:38])[NH:30][C:31]([CH3:37])=[CH:32][C:33]=1[CH:34]([CH3:36])[CH3:35].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2... | Cc1cc(C(C)C)c(CN)c(=O)[nH]1 | CCN(c1cc(C(F)(F)F)cc(C(=O)O)c1C)C1CCN(C)CC1 | null | Cl | F[P-](F)(F)(F)(F)F | c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 16 | To a stirred solution of 3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methyl-5-(trifluoromethyl)benzoic acid (crude material, ˜0.313 mmol) and 3-(aminomethyl)-6-methyl-4-(propan-2-yl)-1,2-dihydropyridin-2-one HCl salt (88.0 mg, 0.407 mmol) in DMSO (2.4 mL) was added PyBOP (244 mg, 0.470 mmol) and hunig base (164 ul, 0.939 ... | CCN(c1cc(C(F)(F)F)cc(C(=O)NCc2c(C(C)C)cc(C)[nH]c2=O)c1C)C1CCN(C)CC1 | null | 50.5 | null |
992,863 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:40][N:41]([CH3:46])[CH2:42][C:43](O)=[O:44].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C... | CN(C)CC(=O)O | COC(=O)c1ccc2c(C3CCCCC3)c3n(c2c1)CCNCc1cc(F)ccc1-3 | 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 | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of methyl 14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (from Step 5) in DCM (0.15 M), DIPEA (4 eq.), dimethylglycine (3 eq.) and HATU (2 eq.) were added and the mixture stirred at RT overnight. The solution was diluted with DCM and HCl (1N) and the 2 phases sepa... | COC(=O)c1ccc2c(C3CCCCC3)c3n(c2c1)CCN(C(=O)CN(C)C)Cc1cc(F)ccc1-3 | null | null | null |
269,491 | ord_dataset-a20aed058d7b40bc81fdf50bc5b03f97 | null | 1993-01-01T00:06:00 | true | C([O:3][P:4]([CH2:9][C@H:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)([O:6]CC)=[O:5])C.C[Si](I)(C)C>C(Cl)Cl>[P:4]([CH2:9][C@H:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)([OH:5])([OH:6])=[O:3] | CCOP(=O)(C[C@H]1CCN[C@@H](C(N)=O)C1)OCC | null | null | C[Si](C)(C)I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 16 | A solution of 278 mg of cis-4-diethylphosphonomethyl-2-piperidinecarboxamide in 5 ml of methylene chloride to which is added 0.43 ml of trimethylsilyl iodide is stirred at room temperature for 16 hours. The mixture is evaporated to dryness, the residue is dissolved in water, and the solution is evaporated to dryness. A... | NC(=O)[C@H]1C[C@@H](CP(=O)(O)O)CCN1 | null | null | null |
1,095,263 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | CON(C)[C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][CH:16]=2)[CH:10]=1)=[O:5].[O:24]1[CH:28]=[CH:27][CH:26]=[CH:25]1>>[C:13]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([C:25]3[O:24][CH:28]=[... | c1ccoc1 | CON(C)C(=O)c1cn(-c2cccc(-c3ccccc3)c2)cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared by method C using compound 12a and furan. HRMS (ESI+): m/z=315.1138 [M+H] | O=C(c1cn(-c2cccc(-c3ccccc3)c2)cn1)c1ccco1 | null | null | null |
1,064,266 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[O:5][CH:6]=1.[H-].[Na+].I[CH3:12]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][O:8][CH3:12])[O:5][CH:6]=1 | OCc1cc(Br)co1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 1.062 g (4-bromo-furan-2-yl)-methanol in 10 ml dimethylsulfoxide was added 0.288 of sodium hydride (55%) in oil and 0.56 ml of iodomethane and the reaction mixtures was stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The phases were separated;... | COCc1cc(Br)co1 | null | null | null |
590,518 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].Cl[C:28]([O:30][CH:31]=[CH2:32])=[O:29]>ClCCCl>[CH:31]([O:30][C:28]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[CH:6... | C=COC(=O)Cl | CCOC(=O)C1CN(Cc2ccccc2)CC1c1ccc([N+](=O)[O-])cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | A stirred solution of 1-benzyl-4-(4-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (9.56 g, Reference Example 6) in 1,2-dichloroethane (25 ml), at 25° C. and under an atmosphere of argon, was treated dropwise with vinyl chloroformate (2.5 ml). The resulting mixture was heated at reflux for 20 hours then evapor... | C=COC(=O)N1CC(C(=O)OCC)C(c2ccc([N+](=O)[O-])cc2)C1 | null | null | null |
1,119,434 | ord_dataset-4226e9b4f9f845db967ed997270dcafc | null | 2011-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([NH:13][CH:14]2[CH2:16][CH2:15]2)=[O:12])=[CH:4][CH:3]=1.CO>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]([CH:14]3[CH2:16][CH2:15]3)[C:11](=[O:12])[NH:10][CH:9]=2)=[CH:4][CH:3]=1 | O=C(NCC(=O)c1ccc(Cl)cc1)NC1CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 1525 mg (6.035 mmol) of N-[2-(4-chlorophenyl)-2-oxoethyl]-N′-cyclopropylurea from Example 113A are suspended in 25 ml of concentrated hydrochloric acid, treated with 25 ml methanol and stirred for one hour at room temperature. The reaction mixture is evaporated to dryness and the residue purified by flash chromatograph... | O=c1[nH]cc(-c2ccc(Cl)cc2)n1C1CC1 | null | null | null |
620,289 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][C:14]([C@@H:16]2[C@@H:20]([OH:21])[CH2:19][CH2:18][NH:17]2)=[O:15])=[CH:5][CH:4]=1)#[N:2].[CH:22](=O)[C:23]([CH3:26])([CH3:25])[CH3:24].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1.CCCCC>[C:23]([C@@H:26]1[N:17]2[CH2:18][CH2:19][C@H:20]([OH:21])[C@H:16]2[C:... | CC(C)(C)C=O | N#Cc1ccc(NC(=O)[C@H]2NCC[C@@H]2O)c2ccccc12 | null | Cc1ccccc1S(=O)(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCC | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | A suspension of 30D (40 mg, 0.14 mmol) and pivalaldehyde (30 μl, 0.27 mmol) in a mixture of dry benzene (0.5 ml) and dry pentane (5.0 ml) was refluxed for 20 hr with a Dean-Starke receiver, after which additional pivalaldehyde (30 μl, 0.27 mmol), dry benzene (0.5 ml) and catalytic toluenesulfonic acid was added (Ref: O... | CC(C)(C)[C@H]1N(c2ccc(C#N)c3ccccc23)C(=O)[C@@H]2[C@@H](O)CCN21 | null | 81.8 | null |
568,854 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[CH2:11][CH2:10]3)[CH:2]=1.S(Cl)([Cl:20])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:20][CH:11]1[CH2:10][C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]=2)[C:12]1=[O:16] | O=C1CCc2cc(-c3cccnc3)ccc21 | O=S(=O)(Cl)Cl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 0 | 0.5 | 3.22 g of 5-pyridin-3-yl-1-indanone are dissolved in 160 ml of dichloromethane and, at 0° C., a solution of 1.34 ml of sulfuryl chloride in 40 ml of dichloromethane is added dropwise over the course of 15 minutes. After stirring at 0° C. for 30 minutes and then at room temperature for 60 minutes, 50 ml of a saturated s... | O=C1c2ccc(-c3cccnc3)cc2CC1Cl | null | null | null |
12,774 | ord_dataset-a0071d97083e4e69ae8872417ed2776b | null | 1976-01-01T00:09:00 | true | [CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[C:34](Cl)=[O:35]>O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=... | Cc1[nH]c2ccccc2c1CCN1CCC(O)C1 | COc1cc(C(=O)Cl)cc(OC)c1OC | null | O=C([O-])[O-] | [Na+] | 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 | 24 | To a suspension of 5 g. (0.02 mole) of 2-methyl-3-[2-(3-hydroxypyrrolidinyl)ethyl]indole and 8 g. (0.075 mole) of sodium carbonate in 40 ml. of chloroform was added 4.2 g. (0.018 mole) of 3,4,5-trimethoxybenzoyl chloride in 30 ml. of chloroform. The mixture was stirred under anhydrous conditions for 24 hours, then trea... | COc1cc(C(=O)OC2CCN(CCc3c(C)[nH]c4ccccc34)C2)cc(OC)c1OC | null | null | null |
521,685 | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | null | 2001-01-01T00:10:00 | true | [CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][N:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[NH2:28][C@H:29]([CH:32]([CH3:34])[CH3:33])[CH2:30][OH:31]>>[OH:31][CH2:30][C@H:29]([NH:28][C:23]([C:22]1[CH:26]=[CH:27][C:... | CC(C)[C@@H](N)CO | CC(C)Nc1cccnc1N1CCN(C(=O)c2ccc(C(=O)O)cn2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the same procedure as described in the example 1, synthesis was carried out starting with 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid and using (R)-(−)-2-amino-3-methyl-1-butanol. Then, the product was recrystallized with acetone and hexane to give a desired compound. | CC(C)Nc1cccnc1N1CCN(C(=O)c2ccc(C(=O)N[C@@H](CO)C(C)C)cn2)CC1 | null | 73 | null |
468,604 | ord_dataset-f1b9e9741a6a4cc68e7070df811f86bb | null | 2000-01-01T00:07:00 | true | [CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:17]([O-])=[O:18])=[C:10]([C:14]([O-])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].Cl.[NH2:24][NH2:25]>CC(O)=O>[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:13][C:12]2=[CH:11][C:10]3[C:14](=[O:15])[NH:24][NH:25][C:17](=[O:18])[C:9]=3[CH... | CCCN(CCC)C1Cc2cc(C(=O)[O-])c(C(=O)[O-])cc2C1 | NN | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 125 | null | A mixture of 2-(dipropylamino)-2,3-dihydro-1H-indene-5,6-dicarboxylate (92, 0.17 g, 0.5 mmol) and hydrazine hydrochloride (0.05 g, 0.7 mmol) in glacial HOAc (10 mL) was refluxed at 125° C. for 4 h. The reaction was cooled, concentrated, and converted to an HCl salt. The resulting solid was recrystallized from EtOAc/MeO... | CCCN(CCC)C1Cc2cc3c(=O)[nH][nH]c(=O)c3cc2C1 | null | null | null |
493,192 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [CH3:1][C@H:2]([CH2:32][CH2:33][NH:34][CH2:35][N:36]=[N:37][N+:38]([O-:40])=[O:39])[C@H:3]([NH:12][C:13](=[O:31])[C@H:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C@@H:15]([N:17]([CH:25]=[O:26])[O:18]C1CCCCO1)[CH3:16])[C:4](=[O:11])[NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1>C(O)(=O)C>[CH3:1][C@H:2]([CH2:32][CH2:33][NH:34][CH2:35... | CC(C)C[C@@H](C(=O)N[C@H](C(=O)Nc1nccs1)[C@H](C)CCNCN=N[N+](=O)[O-])[C@H](C)N(C=O)OC1CCCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 40 | null | (2R,3S)-3-(Formyl-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)butanoic acid [(1S,2R)-2-methyl-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide (30 mg, 0.049 mmol) is dissolved in 2 mL of 80% acetic acid and heated at 40° C. for 20 h. Concentration in vacuo, trituration with dichloromethan... | CC(C)C[C@@H](C(=O)N[C@H](C(=O)Nc1nccs1)[C@H](C)CCNCN=N[N+](=O)[O-])[C@H](C)N(O)C=O | null | 106 | null |
37,034 | ord_dataset-3e699bae9dce4a0f996c34a7c5a4b79a | null | 1978-01-01T00:02:00 | true | [OH:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[S:9][C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl.C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[S:9](=[O:33])[C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][... | O=C(OO)c1cccc(Cl)c1 | O=C(c1ccc(O)cc1)c1sc2ccccc2c1-c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 72 | The product from Example 3 (5.0 g.; 0.0151 mole) and 2.8 g. of m-chloroperbenzoic acid were dissolved together in chloroform. The mixture was allowed to stand at room temperature for about 3 days. The solution then was washed twice with aqueous sodium bicarbonate solution, then with water, and was dried over magnesium ... | O=C(C1=C(c2ccccc2)c2ccccc2S1=O)c1ccc(O)cc1 | null | null | null |
241,763 | ord_dataset-9f54014563f44962b72e288618421b97 | null | 1992-01-01T00:02:00 | true | [C:1]1([C:7]2[C:15]([CH:16]=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]([CH3:21])=[O:20]>C1C=CC=CC=1>[C:1]1([C:7]2[C:15]([CH:16]=[CH:18][C:19](=[O:20])[CH3:21])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[... | CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1 | O=Cc1c(-c2ccccc2)nn2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-phenylpyrazolo[1,5-a]-pyridine-3-carbaldehyde (0.50 g) and acetonylidenetriphenylphosphorane ##STR11## (0.82 g) in benzene (6 ml) was refluxed for 4 hours and then the solvent was evaporated in vacuo. The residue was chromatographed on silica gel (20 g) with chloroform as an eluent. The fractions contain... | CC(=O)C=Cc1c(-c2ccccc2)nn2ccccc12 | null | null | null |
1,394,823 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[O:11]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12]1>>[N+:8]([C:7]1[C:2]([O:16][C@H:13]2[CH2:14][CH2:15][O:11][CH2:12]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9] | O[C@H]1CCOC1 | O=[N+]([O-])c1cccnc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared analogously to I.1 from 2-chlor-3-nitropyridine and (S)-tetrahydro-furan-3-ol. | O=[N+]([O-])c1cccnc1O[C@H]1CCOC1 | null | null | null |
702,861 | ord_dataset-c408dfed796e4354b61e312e67f7143f | null | 2006-01-01T00:04:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([O:17][CH3:23])=[O:16])=[CH:6][CH:7]=1 | CO | O=C(O)CCc1cnoc1-c1ccc(Br)cc1 | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 3-[5-(4-bromophenyl)-4-isoxazolyl]propionic acid (5.00 g), conc. sulfuric acid (0.1 ml) and methanol (100 ml) was refluxed for 4 hr. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brin... | COC(=O)CCc1cnoc1-c1ccc(Br)cc1 | null | 96 | null |
483,538 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | [CH3:1][NH:2][O:3][CH3:4].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH2:19][O:20][C:21]1[C:30]2[C:25](=[CH:26][C:27]([Cl:34])=[C:28]([C:31](O)=[O:32])[CH:29]=2)[NH:24][C:23](=[O:35])[C:22]=1[C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]... | Cc1cc(C)cc(-c2c(OCCC3CCCCN3C(=O)OC(C)(C)C)c3cc(C(=O)O)c(Cl)cc3[nH]c2=O)c1 | CNOC | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | Cl | 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 | 25 | 36 | To a solution of N,O-dimethylhydroxylamine (1.14 g in 50 mL dry methylene chloride) was added 1.5 mL triethylamine followed by 4-[2-(1 -tert-butoxycarbonylpiperidin-2-yl)-ethoxy]-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinoline-6-carboxylic acid (EXAMPLE 4.1, Step F, 1.35 g), 1-(3-dimethylaminopropyl)-3-ethyl... | CON(C)C(=O)c1cc2c(OCCC3CCCCN3C(=O)OC(C)(C)C)c(-c3cc(C)cc(C)c3)c(=O)[nH]c2cc1Cl | null | 81.1 | null |
623,861 | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | null | 2004-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][C:24]=1[N+:31]([O-:33])=[O:32])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].Cl>O.C(O)C>[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26](/[CH:27]=[... | O=Cc1ccc(OCc2ccccc2)c([N+](=O)[O-])c1 | CC(=O)c1cc(C)cc([N+](=O)[O-])c1O | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 3 | 2-hydroxy-5-methyl-3-nitroacetophenone (200 mg, 1.02 mmol), 4-benzyloxy-3-nitrobenzaldehyde (300 mg, 1.16 mmol) and 3 equivalents of sodium hydroxide (120 mg) were introduced into 80% aqueous ethanol solution and the resulting mixture was stirred for 3 hours at room temperature. The reaction solution was acidified by 2... | Cc1cc(C(=O)/C=C/c2ccc(OCc3ccccc3)c([N+](=O)[O-])c2)c(O)c([N+](=O)[O-])c1 | null | 97 | null |
1,297,390 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | CO[C:3](=[O:20])[C@@H:4]([N:6]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:7][CH:8]=O)[CH3:5].Cl.[CH3:22][O:23][C:24](=[O:31])[C:25]([CH3:30])([CH3:29])[CH2:26][CH2:27][NH2:28]>>[CH2:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][N:28]([CH2:27][CH2:26][C:25]([C:24]([O:23][CH3:22])=[O:31])([C... | COC(=O)[C@H](C)N(CC=O)C(=O)OCc1ccccc1 | COC(=O)C(C)(C)CCN | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to the procedure described in Example 12D, (S)-2-[benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester (intermediate 12C) and 4-amino-2,2-dimethyl-butyric acid methyl ester, hydrochloride (intermediate 27) gave the titled compound in 90% yield as light yellow oil. MS: 377.21 (MH+). | COC(=O)C(C)(C)CCN1CCN(C(=O)OCc2ccccc2)[C@@H](C)C1=O | null | 90 | null |
461,476 | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | null | 2000-01-01T00:04:00 | true | [OH-].[K+].[F:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1>CO>[F:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:17]1[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH:16]=1)=[CH:7][NH:8]2 | Fc1cccc2[nH]ccc12 | CN1CCC(=O)CC1 | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 28 | To a solution of 1.18 gm (21.0 mMol) potassium hydroxide in 10 mL methanol were added 1.00 gm (7.4 mMol) 4-fluoro-1H-indole and 1.82 mL (14.8 mMol) 1-methyl-4-piperidone. The reaction mixture was stirred for 28 hours at reflux and then was allowed to cool. The crystals which formed were filtered, washed with methanol a... | CN1CC=C(c2c[nH]c3cccc(F)c23)CC1 | null | 68.7 | null |
1,747,707 | ord_dataset-60a3e71da3174666a50a61dcfa611a9f | null | 2016-01-01T00:07:00 | true | [CH2:1](Br)[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[N:8]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:38]=[C:26]4[CH:27]=[CH:28][CH:29]=[C:30]([C:31]5[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=5)[N:25]4[N:24]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[... | Oc1cccc(-c2cccc3nc(Nc4ccc(OCCN5CCCC5)cc4)nn23)c1 | BrCC1CCCO1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 80 | null | Tetrahydrofurfuryl bromide (20 mg, 0.18 mmol) was added to a stirred solution of 3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-phenol (50 mg, 0.12 mmol) and potassium carbonate (25 mg, 0.18 mmol) in dimethylformamide (1.5 ml). The mixture was heated overnight at 80° C. then cooled ... | c1cc(OCC2CCCO2)cc(-c2cccc3nc(Nc4ccc(OCCN5CCCC5)cc4)nn23)c1 | null | null | null |
1,053,379 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [OH-].[Na+].C[O:4][C:5](=[O:44])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:41][CH3:42])([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30]([OH:39])([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])=[C:24]([CH3:40])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:43])=[CH:9][CH:8]=... | CCC(CC)(c1ccc(C#CC(O)(C(F)(F)F)C(F)(F)F)c(C)c1)c1ccc(-c2ccc(CC(=O)OC)cc2)c(C)c1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 60 | 1 | A 1 N sodium hydroxide aqueous solution (0.102 mL, 0.102 mmol) was added to a solution of (4′-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 45-(2); 20 mg, 0.034 mmol) in methanol-tetrahydrofuran (1:1, 2 mL), and t... | CCC(CC)(c1ccc(C#CC(O)(C(F)(F)F)C(F)(F)F)c(C)c1)c1ccc(-c2ccc(CC(=O)O)cc2)c(C)c1 | null | 76.5 | null |
1,404,415 | ord_dataset-7456bda2326f4bebaa874a5474d4cc0d | null | 2014-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9]([CH3:11])=[C:8]([CH3:12])[CH2:7][C:6]=1[C:13]([O:15][CH3:16])=[O:14])=[O:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClC1C=CC=CC=1>[CH3:16][O:15][C:13](=[O:14])[C:6]1[C:5](=[CH:10][C:9]([CH3:11])=[C:8]([CH3:12])[CH:7]=1)[C:3]([O:2][CH3:1])=[O:4] | COC(=O)C1=C(C(=O)OC)CC(C)=C(C)C1 | null | null | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Clc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | To a solution of 4,5-dimethyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (3.84 g, 17.1 mmol) in chlorobenzene was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (7.77 g, 34.2 mmol) at room temperature and the resulting mixture was heated to reflux 48 h. The resulting mixture was cooled and filtered... | COC(=O)c1cc(C)c(C)cc1C(=O)OC | null | null | null |
295,976 | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | null | 1994-01-01T00:09:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:17])=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C1(=O)O[CH2:21][CH2:20][O:19]1>[I-].C([N+](CC)(CC)CC)C.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:15])[CH3:16])[C:9]=2[O:17][CH2:21][CH2:20][OH:19])=[CH:... | O=C1OCCO1 | CC(C)c1cccc(-c2ccc(F)cc2)c1O | null | CC[N+](CC)(CC)CC | [I-] | 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 | 155 | null | A mixture of 4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol (1.84 g), ethylene carbonate (0.78 g) and tetraethylammonium iodide (0.68 g) was heated in an oil bath at 155° C. for 2 hours, then was cooled and taken up in dichloromethane. The solution was washed in turn with water, 1N sodium hydroxide, 1N hydrochloric ac... | CC(C)c1cccc(-c2ccc(F)cc2)c1OCCO | null | 26 | null |
960,890 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[S:10]1[CH2:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:14]2[S:10][C:11](=[O:16])[NH:12][C:13]2=[O:15])=[CH:4][CH:3]=1 | O=Cc1ccc(O)cc1 | O=C1CSC(=O)N1 | null | O=C(O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | C1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 4-hydroxybenzaldehyde (3.67 g, 30 mmol), 2,4-thiazolidinedione (3.51 g, 30 mmol) and benzoic acid (4.40 g, 36 mmol) in toluene (100 mL) was added piperidine (4.5 mL, 45 mmol) and the mixture was equipped with a Dean Stark apparatus and brought to a vigorous reflux. After 45 min the mixture was cooled in... | O=C1NC(=O)C(=Cc2ccc(O)cc2)S1 | null | 90.4 | null |
668,688 | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | null | 2005-01-01T00:04:00 | true | C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O1CCOCC1.[Pd]>[CH3:41][O:40][CH2:39][... | COCCCCOc1ccc(C2=CCN(c3ccc(N4CCN(C(=O)OCc5ccccc5)CC4)cc3)CC2)cc1 | null | null | [Pd] | O=C[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CO | null | null | null | null | null | null | null | null | null | 100 | null | To a mixture of 4-[4-[4-[4-(4-methoxybutoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]phenyl]piperazine-1-carboxylic acid benzyl ester (2.20 g) and ammonium formate (1.25 g) in 90% methanol (44 ml) and dioxane was added 10% palladium on carbon at room temperature. The reaction mixture was heated at 100° C. for 2 hours. After... | COCCCCOc1ccc(C2CCN(c3ccc(N4CCNCC4)cc3)CC2)cc1 | null | 81.1 | null |
1,573,024 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.C(N(CC)CC)C.[C:18]([NH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(O)C>[C:21]([O:20][C:18](=[O:19])[NH:25][CH:26]1[CH2:31][CH2:30][N:29]([C:2]2[N:7]=[CH:6][N:5]=[C:4]3[NH:8][N:9]=[CH:10][C:3]=23)[CH2:... | Clc1ncnc2[nH]ncc12 | CC(C)(C)OC(=O)NC1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CCO | null | null | null | null | null | null | null | null | null | 80 | null | To a solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (J. Amer. Chem. Soc. 1957, 79, 6407-6413) (59 mg, 0.38 mmol) in ethanol (2 ml) was added triethylamine (100 μl, 0.72 mmol) and 4-(N-Boc-amino)piperidine (134 mg, 0.67 mmol). The solution was heated at 80° C. for 3 hours, and then cooled to room temperature. The sol... | CC(C)(C)OC(=O)NC1CCN(c2ncnc3[nH]ncc23)CC1 | null | 26.5 | null |
1,149,407 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[C:3]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15](Cl)[N:14]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[NH2:21][C:22]1[CH:23]=[CH:24][C:25]2[N:31]([CH2:32][CH2:33][O:34][CH3:35])[C:30](=[O:36])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:37]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O)(C)C>O.C([... | CNC(=O)c1cccc(Cl)c1Nc1nc(Cl)ncc1Cl | COCCN1C(=O)CCCc2cc(N)ccc21 | null | CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2 | O=C([O-])O | [Na+] | 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 | 120 | null | A microwave vessel was charged with 3-chloro-2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide (50.00 mg, 0.1508 mmol), 7-amino-1-(2-methoxy-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one (39 mg, 0.16 mmol), 10-camphorsulfonic acid (6.0 mg, 0.026 mmol) and isopropyl alcohol (2 mL) and heated to at 120° C. for 70 mi... | CNC(=O)c1cccc(Cl)c1Nc1nc(Nc2ccc3c(c2)CCCC(=O)N3CCOC)ncc1Cl | null | 29.9 | null |
1,573,136 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:10][C:3]=12.[CH3:17][C:18]1[C:26]([NH2:27])=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2>>[CH3:17][C:18]1[C:26]([NH:27][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[O:10... | Clc1ccnc2cc(-c3ccccc3)oc12 | Cc1c(N)ccc2[nH]ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by procedure E using 7-chloro-2-phenylfuro[3,2-b]pyridine (60.00 mg; 0.26 mmol; 1.00 eq.) instead of 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine, and 4-methyl-1H-indol-5-ylamine (40.10 mg; 0.27 mmol; 1.05 eq.) instead of 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one and was o... | Cc1c(Nc2ccnc3cc(-c4ccccc4)oc23)ccc2[nH]ccc12 | null | null | null |
908,103 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | I[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH2:33][NH2:34])[C:28]([C:31]#[CH:32])=[N:29][CH:30]=2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH2:33][... | C#Cc1ncc(-c2ccc(Cl)cc2)cc1CN | CC1CCN(CCOc2ccc(I)cc2)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product was prepared analogously to Example 7.1e starting from 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidine and [5-(4-chlorophenyl)-2-ethynylpyridin-3-yl]methylamine. Yield: 70 mg (21% of theoretical); C28H30ClN3O (M=460.010); calc.: molpeak (M+H)+:460/462 (Cl); found: molpeak (M+H)+:460/462 (Cl); HPLC-MS: 5.30 mi... | CC1CCN(CCOc2ccc(C#Cc3ncc(-c4ccc(Cl)cc4)cc3CN)cc2)CC1 | null | null | null |
587,644 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[OH:22])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O>>[OH:22][C:15]1[C:16]([O:20][CH3:21])=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1[N:9]=[C:8]([C:6]2[CH:5]... | Cc1cccc(B(O)O)c1O | COc1cccc(-c2cccc(-c3cccc(Br)n3)n2)c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 6-(2-Hydroxy-3-methoxyphenyl)-6′-(2-hydroxy-3-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine and 2-hydroxy-3-methylphenylboronic acid in 59% yield using method F; δH [2H6]-DMSO 13.28,(1H, s), 8.37,(1H, d), 8.35,(1H, d), 8.29,(2H, t), 8.18,(1H, d), 8.10,(1H, d), 7.... | COc1cccc(-c2cccc(-c3cccc(-c4cccc(C)c4O)n3)n2)c1O | null | 59 | null |
1,308,198 | ord_dataset-78c3f723155a4347a902b53bcee1524d | null | 2013-01-01T00:06:00 | true | [CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20](F)=[C:19]([C:24]#[N:25])[CH:18]=2)(=[O:16])=[O:15])[C:6]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[... | C1COCCN1 | COC(=O)Cc1c(C)n(S(=O)(=O)c2ccc(F)c(C#N)c2)c2ncccc12 | 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 | 25 | 2 | To a solution of [1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (Example 54a) (60.7 mg, 0.157 mmol) in acetonitrile (3 ml) is added potassium carbonate (43.3 mg, 0.314 mmol) followed by morpholine (27.6 μl, 0.314 mmol). The reaction mixture is stirred at room temp... | COC(=O)Cc1c(C)n(S(=O)(=O)c2ccc(N3CCOCC3)c(C#N)c2)c2ncccc12 | null | null | null |
1,032,636 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | C([O:5][C:6](=[O:40])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C@@H:18]([S:19][CH2:20][C:21]([C:23]3[CH:31]=[CH:30][C:26]4[CH2:27][CH2:28][O:29][C:25]=4[CH:24]=3)=[O:22])[C:17](=[O:32])[N:16]2[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:11][CH:10]=1)(C)(C)C>C(O)=O>[O:29]1[C:25]2[CH:24]=[C:23]([C:... | CC(C)(C)OC(=O)COc1ccc([C@@H]2[C@@H](SCC(=O)c3ccc4c(c3)OCC4)C(=O)N2c2ccc(F)cc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=CO | null | null | null | null | null | null | null | null | null | null | 25 | 1 | {4-[(2R,3R)-3-[2-(2,3-Dihydro-benzofuran-6-yl)-2-oxo-ethylsulfanyl]1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetic acid tert-butyl ester (77 mg, 0.137 mmol) was dissolved in formic acid (3 mL) and the solution was stirred for 1 h at room temperature. The solvent was removed under reduced pressure and the resid... | O=C(O)COc1ccc([C@@H]2[C@@H](SCC(=O)c3ccc4c(c3)OCC4)C(=O)N2c2ccc(F)cc2)cc1 | null | null | null |
1,616,179 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:6][N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1.[H-].[Na+].[C:35](N1C=CN=C1)(N1C=CN=C1)=[O:36]>C1COCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:3... | O=C(n1ccnc1)n1ccnc1 | Nc1nc(-c2nn(Cc3ccccc3F)c3ncccc23)ncc1C(=O)NCC(F)(F)F | null | [H-] | [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 | 0.42 | 50 mg (0.11 mmol) of 4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyrimidine-5-carboxamide (example 103A) were initially charged in 5 ml of THF and, while cooling with ice, 18.0 mg (0.45 mmol) of sodium hydride (60% in mineral oil) were added over a period of 5 min. The mixture ... | O=c1[nH]c2nc(-c3nn(Cc4ccccc4F)c4ncccc34)ncc2c(=O)n1CC(F)(F)F | null | null | null |
1,676,310 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:3]=1.[O:17]=[C:18]1[NH:23][CH:22]=[C:21]([CH2:24][C:25]#[N:26])[CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][C:12]1[CH:11]=[C:10]([C:4]2[N:3]=[C:2]([O:17][C:18]3[N:23]=[CH:22][C:21]([CH2:24][C:25]#[N:... | CCc1cc(Cl)nc(-c2cccc(Cl)c2)n1 | N#CCc1ccc(=O)[nH]c1 | 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 solution of 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.300 g, 1.19 mmol), 2-(6-oxo-1,6-dihydropyridin-3-yl)acetonitrile (0.239 g, 1.78 mmol), and potassium carbonate (0.246 g, 1.78 mmol) in DMF (3 mL) was heated with microwave irradiation to 120° C. for 1 h. After this time, the reaction was cooled and concentr... | CCc1cc(Oc2ccc(CC#N)cn2)nc(-c2cccc(Cl)c2)n1 | null | 15.8 | null |
394,916 | ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | null | 1998-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[N+:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11]>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:1][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=2)=[O:18])=[CH:20][CH:21]=1)([O-:12])=[O:11] | O=C(O)c1ccc([N+](=O)[O-])cc1 | Cc1cc(C)cc(N)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 | Using 3,5-xylidine (1.42 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.72 g (quantitative) of the title compound in the form of light yellow crystals. | Cc1cc(C)cc(NC(=O)c2ccc([N+](=O)[O-])cc2)c1 | null | null | null |
1,000,766 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:33])[C:25]4[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=4[F:32])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[N:34]1([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=2)[CH2:39][CH2:38][O:37... | Nc1ccc(N2CCOCC2)cc1 | O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Cl)n2)c1)c1c(F)cccc1F | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 80 | null | To a slurry of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (100 mg, 0.216 mmol.) in 1 mL of EtOH, added 4-(4-morpholinyl)aniline (38 mg, 0.216 mmol.) and 5 μL of conc. HCl. The reaction contents were heated to 80° C. After heating for 18 h, the reaction was cooled to rt and... | O=C(Nc1cccc(-c2nn3ccccc3c2-c2ccnc(Nc3ccc(N4CCOCC4)cc3)n2)c1)c1c(F)cccc1F | null | 43 | null |
980,537 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [CH2:1]([S:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:8]([CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23... | O=C(OO)c1cccc(Cl)c1 | O=c1nc(-c2cccc(CSCc3ccccc3)n2)sc2ccccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 1 | 2-[6-[(Benzylthio)methyl]-2-pyridyl]-4H-1,3-benzothiazine-4-one (0.080 g, 0.22 mmol) was dissolved in chloroform (50 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.037 g, 0.22 mmol) in chloroform (10 ml) was added dropwise thereto. The mixture was stirred at room temperature for 1 hr. The solvent was evapor... | O=c1nc(-c2cccc(CS(=O)Cc3ccccc3)n2)sc2ccccc12 | null | 61.4 | null |
136,311 | ord_dataset-3007013966624a1096d71142f31cb5a3 | null | 1985-01-01T00:10:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C(OCC)(=O)C>[C:35]1([CH3:36])[CH:37]=[CH:38][C:32]([S:29]([... | Cc1ccc(S(=O)(=O)Cl)cc1 | O=C(OCc1ccccc1)N1CCC(CCCCCO)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | null | To a chilled mixture of 5-(1-benzyloxycarbonyl-4-piperidyl)pentanol (18 g) and pyridine (150 ml) is added portionwise tosyl chloride (14.6 g) for 30 minutes with stirring. After stirring for further 1 hour at ice-bath temperature, ice water (2 ml) is added dropwise and the resulting mixture is dissolved in ethyl acetat... | Cc1ccc(S(=O)(=O)OCCCCCC2CCN(C(=O)OCc3ccccc3)CC2)cc1 | null | 66.5 | null |
454,750 | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | null | 2000-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:26])([F:25])[F:24])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH:11]=[CH:10]1>C(CN)O>[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:26])([F:... | Cc1cc(F)ccc1-n1ccc2c(Cl)nc3c(OC(F)(F)F)cccc3c21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NCCO | null | null | null | null | null | null | null | null | null | null | null | null | 1-(2-Methyl-4-fluorophenyl)-4-chloro-6-trifluoromethoxypyrrolo[3,2-c]quinoline(394 mg, 1.0 mmol) was dissolved in ethanolamine(5 ml) in the pressure tube, and reacted at the same condition of Step 3 in the Example 20 to obtain 478 mg of desired compound as solid in 90% of yield. | Cc1cc(F)ccc1-n1ccc2c(NCCO)nc3c(OC(F)(F)F)cccc3c21 | null | 228 | null |
1,314,835 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[NH2:25][C:26]1[N:35]=[C:34]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:33]2[C:28](=[CH:29][C:30]([C:43]([OH:45])=O)=[CH:31][CH:32]=2)[N:27]=1.CN(C)C=O.C(N(CC)C(C)C)(C)C.[NH2:60][C@@H:61]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][CH:72]([CH3:74])... | CC(C)Oc1ccc(C[C@H](N)C#N)cc1 | CN1CCN(c2nc(N)nc3cc(C(=O)O)ccc23)CC1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.17 | N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (42 mg, 0.11 mmol) was added to a solution of 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid (20 mg, 0.07 mmol) in N,N-dimethylformamide (2 mL, 20 mmol) and N,N-diisopropylethylamine (24 uL, 0.14 mmol). The reaction was stirred... | CC(C)Oc1ccc(C[C@@H](C#N)NC(=O)c2ccc3c(N4CCN(C)CC4)nc(N)nc3c2)cc1 | null | 12.1 | null |
1,476,637 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[SH:9].Br[CH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15] | Nc1cc(F)ccc1S | COC(=O)c1ccccc1CBr | 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 | Following General Procedure A, the title compound (1.8 g, 60%) was prepared from 2-amino-4-fluorobenzenethiol (1.4 g, 9.79 mmol) and methyl 2-(bromomethyl)benzoate (2.2 g, 9.79 mmol), K2CO3 (4.0 g, 29.4 mmol) in DMF (50 ml). | COC(=O)c1ccccc1CSc1ccc(F)cc1N | null | 63.1 | null |
360,750 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Cl.[OH-].[Na+]>>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][CH:8]([C:6]2[CH:5]=[CH:4][C:3]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3... | ClCc1ccc(Cl)c(Cl)c1 | CC(=O)Cc1ccc(-c2ccccc2)c(F)c1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | 6 | 45.1 g of the ketone compound thus obtained, 50.3 g of 3,4-dichlorobenzyl chloride and 15.8 g of sodium hydroxide were mixed, heated with stirring at 100° C. for 6 hours. The reaction solution was left to cool to room temperature and then extracted by an addition of ethyl acetate and water. The organic layer was post-t... | CC(=O)C(Cc1ccc(Cl)c(Cl)c1)c1ccc(-c2ccccc2)c(F)c1 | null | 84.9 | null |
856,238 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:20]([CH:22]([NH:25][C:26](=O)[O:27]C1C=CC=CC=1)[CH2:23][CH3:24])[CH3:21]>CN(C)C=O>[CH2:20]([CH:22]([NH:25][C:26]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:16]=[CH:15][N:14]=[... | CCC(CC)NC(=O)Oc1ccccc1 | Nc1cc(Oc2ccc3[nH]ccc3c2)ccn1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 25 | null | 4-(1H-5-Indolyloxy)-2-pyridinamine (1.85 g, 8.2 mmol, CAS No. 417722-11-3) which was described in WO 02/32872 was dissolved in N,N-dimethylformamide (20 ml); and sodium hydride (394 mg, 9.84 mmol) was added thereto while stirring at room temperature. The reaction mixture was cooled with ice bath after 30 minutes; pheny... | CCC(CC)NC(=O)n1ccc2cc(Oc3ccnc(N)c3)ccc21 | null | 70.7 | null |
965,129 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | Cl.[Cl:2][C:3]1[C:8]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][C:6]([F:17])=[CH:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29].O>CN(C=O)C>[CH3:29][O:28][CH:27]([O:30][CH3:31])[CH2:26][CH2:25][N:13]1[CH:14]=[C:9]([C:8]2[C:3]([Cl:2])=[N:4][CH:5]=[C:6]... | O=c1[nH]cc(-c2cc(F)cnc2Cl)c(=O)[nH]1 | COC(CCBr)OC | null | Cl | O=C([O-])[O-] | [K+] | 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 | null | null | 5-(2-Chloro-5-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep71, 249 mg, 0.9 mmol), K2CO3 (124 mg, 0.9 mmol) and 3-bromo-1,1dimethoxy-propane (205 mg, 1.1 mmol) were suspended in DMF (3 ml). After stirring the reaction at room temperature for 18 hours, water was added. The aqueous layer washed with die... | COC(CCn1cc(-c2cc(F)cnc2Cl)c(=O)[nH]c1=O)OC | null | 48.5 | null |
1,676,494 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[NH:12][CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=2)=[CH:8][CH:9]=1 | [H][H] | COC(=O)c1c[nH]c(Cc2ccc([N+](=O)[O-])cc2)n1 | 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 | A 100-mL round bottomed flask was charged with methyl 2-[(4-nitrophenyl)methyl]-1H-imidazole-4-carboxylate (220 mg, 0.84 mmol), Pd/C (270 mg, 10 wt %, 0.255 mmol, 0.3 eq.) and EtOH (24 ml). The mixture was stirred under 1 atmosphere of hydrogen overnight. The insoluble material was removed by filtration and the organic... | COC(=O)c1c[nH]c(Cc2ccc(N)cc2)n1 | null | 91.1 | null |
1,319,220 | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | null | 2013-01-01T00:07:00 | true | [NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[CH:19]([C:21]1[N:22]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:23]([CH3:26])=[CH:24][CH:25]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:15]([O:14][C:12](=[O:13])... | CC(C)(C)OC(=O)Cn1ccc2ccc(N)cc21 | Cc1ccc(C=O)n1C(=O)OC(C)(C)C | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | A solution of tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A—for synthesis see above) (1.7368 mmol, 1.1 equiv.) in DCM (3 ml) was added at 0° C. to tert-butyl 2-formyl-5-methyl-1H-pyrrole-1-carboxylate (1.5789 mmol, 1.0 equiv.), dissolved in DCM (12 ml), and the mixture was stirred for 30 min at 25° C. At ... | Cc1ccc(CNc2ccc3ccn(CC(=O)OC(C)(C)C)c3c2)n1C(=O)OC(C)(C)C | null | 58 | null |
1,003,603 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH:13]2[CH2:15][CH2:14]2)[CH:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:33]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)C(C)C)C.[OH-].[K+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH:13]2[CH2:15][CH2:14]2)[CH:10]([NH2:33])[CH2:9]1)=[O:7])([CH3:4])([CH3... | CC(C)(C)OC(=O)N1CC(C(=O)O)C(C2CC2)C1 | [N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 80 | 4 | 101.5 To a stirred solution of 200 mg (3RS,4RS)-4-cyclopropyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester at 80° C. in 2 ml dioxane under an argon atmosphere were added 0.20 ml diphenylphosphoryl azide and 0.16 ml N-ethyldiisopropylamine. Stirring at 80° C. was continued for 4 hrs. Then, the hot mixture was po... | CC(C)(C)OC(=O)N1CC(N)C(C2CC2)C1 | null | null | null |
1,517,099 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-])=O)=[C:6]([CH:17]=1)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[Br:1][C:2]1[CH:17]=[C:6]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([NH2:18])=[CH:4][CH:3]=1 | COc1ccc(CNc2cc(Br)ccc2[N+](=O)[O-])cc1 | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 60 | 4 | To a solution of 5-bromo-N-(4-methoxybenzyl)-2-nitroaniline (750 mg, crude) in EtOH (8 mL) and H2O (8 mL) was added Fe powder (766 mg, 13.7 mmol) and ammonium chloride (733 mg, 13.7 mmol). The mixture was stirred at 60° C. for 4 h then filtered and the filtrate was concentrated to remove EtOH. The residue was then dilu... | COc1ccc(CNc2cc(Br)ccc2N)cc1 | null | 80.5 | null |
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