Dimethylformamide → HCID 92131116, compound

Participants

Reaction Steps

To a solution of 8-(trifluoromethoxy)-5,6-dihydro-4H-benzo[f][1,2,3]triazolo[1,5-a]azepine-3-carboxylic acid (169 mg, 0.540 mmol) in dry DCM (2 mL) under nitrogen was added oxalyl chloride (0.052 mL, 0.593 mmol) and DMF (0.084 mL, 1.079 mmol) and the mixture was stirred for 15 mins. 4-Amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate A) (124 mg, 0.593 mmol) was added followed by triethylamine (0.226 mL, 1.619 mmol) and the mixture was stirred at RT for 16 hrs. The resultant mixture was diluted with DCM and water and stirred vigorously. The mixture was passed through a phase separating cartridge and the organic portion was concentrated under reduced pressure to give a yellow oil. The oil was absorbed onto silica and purified by chromatography eluting with 100% TBME. The product fractions were combined and concentrated under reduced pressure to give a glassy solid which was recrystallised from 1:1 diethylether:EtOAc. The resulting crystals were filtered under gravity to give the title compound as a white solid.

Provenance & Evidence