Ammonium Chloride → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-dimethylcarbamoylmethyl-3,5-bis-trifluoromethyl-benzamide

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Reaction Steps

A solution of {(3,5-bis-trifluoromethyl-benzoyl)-[4-(2-chloro-phenyl)-pyridin-3-yl]-amino}-acetic acid (0.15 g, 298 μmol, example 102, intermediate), HATU (136 mg, 358 μmol) and diethylamin hydrochloride (29.2 mg, 358 μmol) in DMF (2 mL) was treated with DIPEA (116 mg, 156 μL, 895 μmol) and stirred at room temperature for 1.75 h. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were washed twice with water and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light yellow foam (0.127 g; 80%). MS (ESI): m/z=530.12 [M+H]+.

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