Morpholine → [8-Methyl-3-(1-{4-[5-(morpholin-4-ylcarbonyl)pyridin-2-yl]phenyl}cyclopropyl)-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl]methanol

Participants

Reaction Steps

A solution of the compound (200 mg, 0.458 mmol) obtained in Example 66, morpholine (200 μL, 2.29 mmol), N,N-dimethylaminopyridine (6 mg, 46 μmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (264 mg, 1.37 mmol) in N,N-dimethylformamide (4.00 mL) was stirred at room temperature for 14 h. Saturated aqueous sodium hydrogencarbonate (100 mL) was added to the reaction mixture, the mixture was extracted with dichloromethane, and the organic layer was washed with water and dried with anhydrous sodium sulfate. Then the solvent was distilled off under reduced pressure. The residue was purified by preparative TLC (dichloromethane:methanol=9:1) to obtain the title compound (69 mg, 11%) as a white solid.

Provenance & Evidence