Diisopropylethylamine → (1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-methanone

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Reaction Steps

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (200 mg, 0.64 mmol) in DMF (8 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (227 mg, 0.70 mmol), N,N-diisopropyl ethyl amine (550 μL, 3.2 mmol) and thiomorpholine 1,1-dioxide (0.104 g, 0.77 mmol). The resulting reaction mixture was stirred for 30 min at room temperature and diluted with water. The mixture was then extracted with ethyl acetate and the combined organic layers washed with aqueous sodium carbonate (saturated) and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 6:4) afforded the title compound (176 mg, 63%) as a white solid. MS: m/e=429.2 [M+H]+.

Provenance & Evidence