Ethyl Acetate → HCID 9913371, compound

Participants

Reaction Steps

To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (90 mg, 0.19 mmol) in 10 ml 1:1 ethyl acetate:anhydrous methanol cooled to −78° C. was bubbled HCl gas until saturation was achieved. Reaction was placed in the refrigerator at 0° C. over the weekend. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried methyl imidate residue was dissolved in 5 ml anhydrous methanol to which ammonium acetate (144 mg, 2 mmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated then treated with 10 ml trifluoroacetic acid for 2 hrs, concentrated and purified on a 2×25 cm Vydac C18 HPLC column to give 3-((1E)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-1-(trifluoromethyl)vinyl)benzenecarboxamidine (57 mg, 47%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 489.15

Provenance & Evidence