Ammonium Chloride → 2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzamide

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Reaction Steps

To a solution of 0.10 g (0.21 mmol) 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid (Example 29, intermediate) in 1 mL N,N-dimethylformamide were added 0.022 g (0.41 mmol) ammonium chloride, 0.028 g (0.21 mmol) 1-hydroxybenzotriazole, 0.07 mL N,N-diisopropylethylamine and 0.040 g (0.21 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride. The resulting mixture was stirred at room temperature overnight, filtered over a syringe micro filter and purified on a preparative HPLC system (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to afford 80 mg (80%) of the desired compound as a light brown solid. MS (ESI): m/z=483.098 [M+H]+.

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