Synthesis of HCV replicase inhibitors: Base-catalyzed synthesis of protected α-hydrazino esters and selective aerobic oxidation with catalytic Pt/Bi/C for synthesis of imidazole-4,5-dicarbaldehyde

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 11680-11690

  Bowman, Roy K ^a   Brown, Andrew D ^a   Cobb, Jannine H ^a   Eaddy, John F ^a   Hatcher, Mark A ^a   Leivers, Martin R ^a   Miller, John F ^a   Mitchell, Mark B ^a   Patterson, Daniel E ^a   Toczko, Matthew A ^a   Xie, Shiping ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; AEROBIC OXIDATIONS; CARBOXYLIC ESTERS; CONVERGENT SYNTHESIS; CYCLOCONDENSATION; ESTER ENOLATES; INORGANIC BASIS; PYRIDAZINE;

CARBOXYLATION; CATALYSIS; CATALYTIC OXIDATION; ESTERIFICATION;

ESTERS;

2 (2,3 DIFLUOROPHENYL) 1H IMIDAZOLE; 2 (2,3 DIFLUOROPHENYL) 1H IMIDAZOLE 4,5 DICARBALDEHYDE; 2 (2,3 DIFLUOROPHENYL) 5H IMIDAZO[4,5 D]PYRIDAZINE; 2 [(2 HYDROXYETHYL)OXY]ETHYL[2 (2,3 DIFLUOROPHENYL) 5H D]PYRIDAZIN 5 YL][3 (4 (PROPYLOXY) 2 (TRIFLUOROMETHYL)PHENYL 5 ISOXAZOLYL]ACETATE; 2 [3 [4 (PROPYLOXY) 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ETHANOL; 2 [3 [4 BROMO 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ETHANOL; 2 [3 [4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL] 5 SIOXAZOLYL]ETHANOL; 4 BROMO 2 (TRIFLUOROMETHYL)BENZALDEHYDE OXIME; [2 (2,3 DIFLUOROPHENYL) 1H IMIDAZOLE 4,5 DIYL]DIMETHANOL; [3 [4 (PROPYLOXY) 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ACETIC ACID; [3 [4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ACETIC ACID; ALDEHYDE; BASE; BIS(1,1 DIMETHYLETHYL) 1 [1 (3 (4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL) 5 ISOXAZOLYL) 2 (METHOXY) 2 OXOETHYL] 1,2 HYDRAZINEDICARBOXYLATE; ESTER; HYDRAZINE; HYDRAZINE DERIVATIVE; IMIDAZOLE DERIVATIVE; METHYL 2 HYDRAZINYL 2 [3 [4 PROPOXY 2 (TRIFLUOROMETHYL)PHENYL]ISOXAZOL 5 YL]ACETATE; METHYL [3 [4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL][2 (2,3 DIFLUOROPHENYL) 5H IMIDAZO[4,5 D]PYRIDAZIN 5 YL]ACETATE; METHYL[2 (2,3 DIFLUOROPHENYL) 5H IMIDAZO[4,5 D]PYRIDAZIN 5 YL][3 [4 (PROPYLOXY) 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ACETATE; METHYL[3 [4 (PROPYLOXY) 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ACETATE; METHYL[3 [4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL]ACETATE; PRODRUG; PROPYL [3 [4 CYCLOPROPYL 2 (TRIFUOROMETHYL)PHENYL] 5 ISOXAZOLYL][2 (2,3 DIFLUOROPHENYL) 5H OMIDAZO[4,5 D]PYRIDAZIN 5 YL]ACETATE; PROPYL[3 [4 CYCLOPROPYL 2 (TRIFLUOROMETHYL)PHENYL] 5 ISOXAZOLYL][2 (2,3 DIFLUOROPHENYL) 5H IMIDAZO[4,5 D]PYRIDAZIN 5 YL]ACETATE; PYRIDAZINE; UNCLASSIFIED DRUG; VIRUS ENZYME;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CONTROLLED STUDY; DECARBOXYLATION; DEPROTECTION REACTION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

ALDEHYDES; ANTIVIRAL AGENTS; BISMUTH; CARBON; CATALYSIS; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTERS; HEPACIVIRUS; HYDROXIDES; IMIDAZOLES; LITHIUM CARBONATE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PLATINUM; POTASSIUM COMPOUNDS; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 84890228524     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4014595     Document Type: Article

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