Methanesulfonyl chloride → N-[1-benzenesulfonyl-4-(1-methanesulfonyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.166 ml, 0.954 mmol) and methanesulfonyl chloride (0.027 ml, 0.350 mmol), were added sequentially to a solution of crude N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide (hydrochloride salt) (0.382 mmol, obtained in preceding step) in CH2Cl2 (10 ml) at 25° C. The reaction mixture was stirred for 30 min at 25° C., then was partitioned between half-saturated NaHCO3 (75 ml) and CH2Cl2 (100 ml). The organic layer was dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure to afford N-[1-benzenesulfonyl-4-(1-methanesulfonyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyclopentyl-acetamide as a white foam. LCMS (Method G, ESI): RT=0.93 min, m+H=560.3. This material was used in the next step below without additional purification or characterization.

Provenance & Evidence