4-Methylmorpholine → HCID 20740224, compound

Participants

Reaction Steps

To (1R,2S)-2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarboxylic acid from Example 3 (200 mg, 0.67 mmol) was added EDCI (150 mg, 0.78 mmol), HOBT (110 mg, 0.82 mmol), anhydrous DMF (4 mL), N-methylmorpholine (0.15 mL, 1.3 mmol), and 4-pyridylglycine nitrile hydrochloride salt (4) (160 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 20 hrs, then 50 mL of water was added and extracted with three 50 mL portions of ethyl acetate. The combined organic layers was washed with three 50 ml portions of water and three 50 mL portions of saturated NaHCO3, dried over sodium sulfate, filtered and concentrated to give a crude foam. Purification by column chromatography (5:95 methanol:dichloromethane) gave 1-methyl-1H-indole-2-carboxylic acid {(1S,2R)-2-[(cyano-pyridin-4-ylmethyl-methyl)-carbamoyl]cyclohexyl}-amide ,165 mg, 58%). MS: 430 (M+H+).

Provenance & Evidence