2-Methoxyethylamine → 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-N-(2-methoxy-ethyl)-nicotinamide

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminium solution (2 M in toluene, 0.80 mL, 1.60 mmol) was added to a solution of 2-methoxyethylamine (93.3 μL, 1.06 mmol) in dioxane (4 mL). The mixture was stirred for 45 min 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 (4 mL) was added and 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=2:3 to 1:0) to afford the title compound (14 mg, 13%) as a white solid. MS: m/e=418.2 [M−H]−.

Provenance & Evidence