Acetyl chloride → HCID 11999120, compound

Participants

Reaction Steps

To a solution of rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid (4-amino-phenyl)-amide (55 mg, 0.11 mmol) (from Example 76b supra) in tetrahydrofuran (2 mL) was added triethylamine (16 mg, 0.16 mmol) (Aldrich), followed by the addition of acetyl chloride (10 mg, 0.13 mmol) (Aldrich). The mixture was stirred at room temperature for 20 minutes. The crude was quenched with water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was 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-acetylamino-phenyl)-amide as a white solid (Yield 30 mg, 50%).

Provenance & Evidence