1-Propanesulfonyl chloride → N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide

Participants

Reaction Conditions

Reaction Steps

Diisopropylethylamine (0.107 ml, 0.615 mmol) and 1-propanesulfonyl chloride (0.035 ml, 0.308 mmol) were added sequentially to a solution of N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyano-acetamide (hydrochloride salt) (0.205 mmol) in CH2Cl2 (2 ml) at 25° C. The reaction mixture was stirred for 3 h at 25° C., then was partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml). The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide as a brown oil/solid. LCMS (Method G, ESI): RT=0.88 min, m+H=545.3. This material was used in the next step below without additional purification or characterization.

Provenance & Evidence