Ammonium Chloride → HCID 11999001, compound

Participants

Reaction Steps

To a solution of rac-4-({3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carbonyl}-amino)-benzoic acid (50 mg, 0.093 mmol) (from Example 64 supra) in DMF (1.5 mL) was added diisopropyl ethylamine (48.0 mg, 0.37 mmol) (Aldrich), followed by the addition N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (35.5 mg, 0.18 mmol) (Aldrich), 1-hydroxybenzotriazole (25.0 mg, 0.18 mmol) (Aldrich) and ammonium chloride (9.8 mg, 0.18 mmol) (Aldrich). The mixture was stirred at room temperature for 2 hours and then heated at 60° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by chromatography to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-carbamoyl-phenyl)-amide as a white solid. (Yield 25 mg, 50%).

Provenance & Evidence