Dimethylformamide → 1-(2,4-Dichlorophenyl)-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-(2,4-dichlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (100 mg, 0.368 mmol), oxalyl chloride (0.048 ml, 0.551 mmol) and DMF (0.057 ml, 0.735 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) (89 mg, 0.404 mmol) was added followed by triethylamine (0.154 ml, 1.103 mmol) and the mixture was stirred at RT for 30 mins. The resulting mixture was diluted with DCM, washed with 0.1M HCl(aq) and sat. NaHCO3(aq) and the organic extracts were passed through a phase separating cartridge and concentrated under reduced pressure. The resultant brown 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 pale pink solid which was triturated with diethylether. The resulting solid was collected by filtration and dried in the vacuum oven to give the title compound as a pale pink solid.

Provenance & Evidence