4-Methylmorpholine → HCID 22711199, compound

Participants

Reaction Conditions

Reaction Steps

In tetrahydrofuran (10 ml), 3-(5-tert-butoxycarbonyl -4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)propionic acid (445 mg) was dissolved, followed by the successive dropwise addition of N-methylmorpholine (170 μl) and isobutyl chloroformate (210 μl) at −20° C. After stirring at −20° C. for 10 minutes, a solution of 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride (607 mg) which had been dissolved in dichloromethane (10 ml) was added. After stirring at −20° C. for 10 minutes, the reaction mixture was warmed up to room temperature. The reaction mixture was concentrated under reduced pressure. The residue was then dissolved in dichloroethane. The resulting solution was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1 to 2:1), whereby the title compound (625 mg, 72%) was obtained.

Provenance & Evidence