Dimethylformamide → 1-(2-Chloro-4-cyclopropylphenyl)-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 Steps

A solution of 1-(2-chloro-4-cyclopropylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (Example 10, step 3) (95 mg, 0.342 mmol), oxalyl chloride (0.045 ml, 0.513 mmol) and DMF (0.053 ml, 0.684 mmol) in DCM (5 ml) was stirred at RT for 15 mins. 4-Amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (83 mg, 0.376 mmol) was added to the mixture followed by triethylamine (0.143 ml, 1.026 mmol) and this was stirred at RT for 30 mins. The resulting mixture was diluted with DCM, washed with 0.1 M HCl(aq) and sat. NaHCO3(aq). The organic extracts were passed through a phase separating cartridge and concentrated under reduced pressure to give a brown oil. The oil was absorbed onto silica and purified by chromatography eluting with 0-10% MeOH in TBME. The product fractions were combined and concentrated under reduced pressure to give a yellow glassy solid. The solid was dissolved in 1:1 EtOAc:Et2O, washed with water (2×), brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a yellow glassy solid.

Provenance & Evidence