4-Methylmorpholine → HCID 20740235, compound

Participants

Reaction Steps

To 62 mg (0.14 mmol) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-(4-amino-benzyl)cyano-methyl]-carbamoyl}cyclohexyl)-amide dissolved in 1 mL DMF was added 16 mg (0.14 mmol) of methanesulfonyl chloride, 2 mg (0.014 mmol) of 4-dimethylaminopyridine, and 0.031 mL (0.28 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate, and concentrated. Reverse phase column chromatography was employed to separate the pure title compound from the unreacted starting material, and provided 10 mg of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-cyano-(4-methanesulfonylamino-benzyl)-methyl]-carbamoyl}-cyclohexyl)-amide. HPLC: 100% pure, yield: 14%, MS: 522 (M+H+).

Provenance & Evidence