Diisopropylethylamine → 5-amino-N-(2-((N-ethyl-2,6-difluorobenzamido)methyl)-3,3,3-trifluoro-2-hydroxypropyl)-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide

Participants

Reaction Steps

To a solution of 5-amino-N-{2-[(ethylamino)methyl]-3,3,3-trifluoro-2-hydroxypropyl}-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide (0.277 g, 0.712 mmol) in dry dichloromethane (ca. 11 ml), diisopropylethylamine (0.245 ml, 1.42 mmol) was added and then cooled in a freezer to −10 to −15° C. before a similarly cooled solution of 2,6-difluorobenzoyl chloride (0.123 g, 0.712 mmol) in dichloromethane (2 ml) was added with stirring. The mixture was stirred for 1 minute and then allowed to stand in the fridge for approx. 2 hours and then allowed to warm to room temperature. The next day the mixture was evaporated under reduced pressure and purified on a column of silica. Elution with 2% ethanol in chloroform gave, upon evaporation under reduced pressure, a clear glass (0.421 g) which, upon scraping, gave the title compound (0.356 g) as a white solid.

Provenance & Evidence