Acetic Anhydride → HCID 20740210, compound

Participants

Reaction Steps

To a solution of 1-methyl-1H-indole-2-carboxylic acid {(1S,2R)-2-[(cyano-piperidin-4-ylmethyl-methyl)-carbamoyl]-cyclohexyl}-amide hydrochloride (0.50 g, 1.06 mmol) in 2 mL of DMF, was added 0.5 mL of TEA, acetic anhydride (0.15 mL, 1.59 mmol), and a few crystals of DMAP. The reaction mixture was stirred at ambient temperature for 1 hour, and partitioned between 50 mL of water and 50 mL of ethyl acetate. The separated organic layer was washed with water (2×50 mL), dried with sodium sulfate, filtered, concentrated, and purified by column chromatography (5:95, MeOH/CH2Cl2) to give 165 mg (33%) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(1-acetyl-piperidin-4-ylmethyl)-cyano-methyl]-carbamoyl}-cyclohexyl)-amide as a white amorphous solid. MS: 478 (M+H+).

Provenance & Evidence