Water → 6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid cyclopropylmethyl-amide

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Reaction Steps

To a solution of aminomethylcyclopropane (0.11 mL, 1.2 mmol) in dioxane (5 mL) was added dropwise trimethylaluminum solution (2 M solution in hexane, 0.62 mL, 1.24 mmol). After stirring for 1 h at room temperature a suspension of 6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester (100 mg, 0.3 mmol) in dioxane (5 mL) was added. The reaction mixture was stirred at 90° C. for 2 h, cooled to room temperature and poured into water. Extraction (ethyl acetate/saturated aqueous Seignette salt solution) followed by drying of the organic phase over sodium sulfate and evaporation afforded an oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100) afforded the title compound (60 mg, 54%) which was obtained as a light yellow foam. MS: m/e=364.5 [M+H]+.

Provenance & Evidence