Cyclopropylamine → N-Cyclopropyl-6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinamide

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminium solution (2 M in toluene, 0.8 mL, 1.60 mmol) was added to a solution of cyclopropylamine (62.0 mg, 1.06 mmol) in dioxane (5 mL). The mixture was stirred for 1 h at 50° C. Then a solution of 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.27 mmol) in dioxane (5 mL) was added. The reaction mixture was stirred overnight at 85° C. The dioxane was removed by distillation. The remaining material was purified by chromatography (silica, ethyl acetate:heptane=8:2 to 1:0) to afford the title compound (27 mg, 25%) as a colourless oil. MS: m/e=402.3 [M+H]+.

Provenance & Evidence