Hydrochloric Acid → 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylic acid

Participants

Reaction Steps

A solution of ethyl 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-1H-pyrazole-3-carboxylate (16.1 mg, 0.0379 mmol) in THF (0.50 mL) was treated with 1.0 M aqueous LiOH (0.0568 mL, 0568 mmol) and the solution was stirred at 40 degrees for 3 days. The reaction was then heated at 65 degrees for 6 hours. The reaction mixture was cooled and acidified with 1N HCl. The solution was extracted with EA (3×25 mL) and the combined organic layers were dried, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase chromatography to give 1 mg (7% yield) of the title compound as a white solid. LC/MS (FA) ES+ 397, 399.

Provenance & Evidence