To a stirred solution of 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (100 mg, 0.421 mmol), oxalyl chloride (0.041 ml, 0.463 mmol) and DMF (0.065 ml, 0.842 mmol) in dry DCM (5 ml) was added a solution of 4-amino-2-(2-fluorophenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate B) (102 mg, 0.463 mmol) in dry DCM (1 ml), followed by triethylamine (0.176 ml, 1.262 mmol) and the mixture was stirred at RT for 1 hr. The resulting mixture was diluted with DCM and 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. The resulting solid 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 glassy solid, which was suspended in 1:1 iso-hexane:Et2O, heated at 50° C. for 2 h, stoppered and allowed to cool for 16 hrs. The solid was collected by filtration and dried on the vacuum line to give the title compound as a pale yellow solid.
