To a stirred solution of (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (101 mg, 0.342 mmol, 1.0 eq) in THF/DMF (1/20, v/v, 2.8 mL) was added 2-(3-fluoro-4-hydroxymethyl)phenyl)propionic acid (68 mg, 0.348 mmol, 1.02 equiv.), HOBt (46 mg. 0.342 mmol, 1 equiv.), TBTU (151 mg, 0.342 mmo, 1 equiv.) and DIPEA (0.232 mL, 176 mg, 1.37 mmol, 4 equiv.) and the mixture was stirred for 3 d at room temperature The reaction mixture was diluted with 20 mL of EtOAc and washed with 20 mL of water. The aqueous phase was extracted with EtOAc (3×20 mL), the combined organic phases were dried over magnesium sulfate, evaporated and the residue was purified by column chromatography (EtOAc/cyclohexane (1:1) as eluent) to give 2-(3-fluoro-4-(hydroxymethyl)phenyl)-N-((1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide (119 mg, 79%).
