To a solution of 2-chloro-5-(5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid (0.028 g, 0.117 mmol) in anhydrous dimethyl formamide (DMF) (4 mL) was added 1-hydroxybenzotriazole (0.018 g, 0.14 mmol). After stirring at room temperature for 10 minutes, 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.025 g, 0.13 mmol) was added. After stirring at room temperature for 30 minutes, 2-chlorophenethylamine (0.018 g, 0.12 mmol) and triethylamine (0.012 g, 0.12 mmol) were added and the mixture stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed sequentially with water and brine, and dried over sodium sulfate. Removal of solvent in vacuo followed by purification by reverse phase HPLC yielded 0.042 g (10%) of the title compound as a colorless solid. 1H NMR (300 MHz, CDCl3) δ (m, 2H), 3.45 (m, 2H), 7.25 (m, 2H), 7.35 (m, 2H), 7.60 (d, J=7.9 Hz, 1H), 7.76 (s, 1H), 7.78 (s, 1H), 8.43 (s, 1H) and 8.64 (m, 1H). Mass Spectrum (M−H) 3:1 Ratio of 375 and 377.
