Dimethylformamide → 1-(2-Chloro-4-(trifluoromethoxy)phenyl)-N-(2-(2-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

DMF (43 μL, 0.56 mmol) was dissolved in DCM (1 mL) and cooled to 0° C. Oxalyl chloride (27 μL, 0.308 mmol) was added followed by 1-(2-chloro-4-(trifluoromethoxy)phenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (90 mg, 0.28 mmol) and the reaction mixture was stirred for 10 min. 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (62 mg, 0.28 mmol) was added, followed by triethylamine (117 μL, 0.839 mmol). The reaction was allowed to warm to RT and stirred for 4 h. Saturated aqueous NaHCO3 was added to the reaction mixture and the product was extracted with DCM. The organic extract was dried and concentrated under reduced pressure. The crude material was purified by reversed phase chromatography (Prep Method G) to afford the title compound.

Provenance & Evidence