Diisopropylethylamine → 6-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-n-((s)-2,2,2-trifluoro-1-methyl-ethyl)-nicotinamide

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Reaction Steps

To a stirred solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) in DMF (2 mL) at room temperature under argon was added L-2,2,2-trifluoro-1-(methyl)ethylamine (ABCR F07820EFA, 42.9 mg, 0.38 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (121.7 mg, 0.38 mmol) and N,N-diisopropylethylamine (222.6 mg, 1.72 mmol). After 2.5 h the reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=1:0 to 2:1) afforded the title compound (89 mg, 67%) as a light yellow oil. MS: m/e=384.3 [M−H]−.

Provenance & Evidence