Ammonium Chloride → HCID 25131772, compound

Participants

Reaction Steps

To a solution of 4-{4-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-yl]-imidazol-1-yl}-benzoic acid (90 mg, 0.22 mmol) in THF (4 mL), was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide HCl (50.7 mg, 0.26 mmol) and N-hydroxybenzotriazole (40.5 mg, 0.0.6 mmol), followed by adding ammonium chloride (40.6 mg, 0.76 mmol) and N,N-diisopropylethylamine (199.2 μL, 1.1 mmol) and the reaction mixture was stirred at room temperature overnight. Then 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide HCl (50.7 mg, 0.26 mmol) and N-hydroxybenzotriazole (40.5 mg, 0.0.6 mmol), followed by adding ammonium chloride (40.6 mg, 0.76 mmol) and N,N-diisopropylethylamine (199.2 μL, 1.1 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was then extracted with ethyl acetate and the combined organic extracts were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100) afforded the title compound (38 mg, 42%) which was obtained as a white solid. MS: m/e=417.4 [M+H]+.

Provenance & Evidence