Diisopropylethylamine → N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzamide

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Reaction Steps

To a solution of 3-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzoic acid (66 mg, 0.3 mmol), PyBrOP (169 mg, 0.37 mmol) and diisopropylethyl amine (263 μL, 1.5 mmol) in DCM (3 mL) at 25° C. was added 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione-HCl (105 mg, 0.3 mmol)[prepared according to Preparation 3]. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica) affording the title compound (112 mg, 68%) as a white solid: LC-MS (ES) m/z=551 (M+H)+.

Provenance & Evidence