Diisopropylethylamine → 2-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide

Participants

Reaction Steps

To a solution of 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acid (83 mg, 0.25 mmol) in DMF (1.5 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (88 mg, 0.28 mmol), N,N-diisopropyl ethyl amine (214 μL, 1.25 mmol) and 4-aminotetrahydropyran (28 mg, 0.28 mmol). The resulting reaction mixture was stirred for 1 h. The reaction mixture was then evaporated and purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) afforded the title compound (68 mg, 66%) as a white solid. MS: m/e=415.3 [M+H]+.

Provenance & Evidence