Diisopropylethylamine → 4-{1-benzenesulfonyl-5-[2-(3-methyl-isoxazol-4-yl)-acetylamino]-1H-pyrrolo[2,3-b]pyridin-4-ylamino}-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-(3-Methylisoxazol-4-yl)acetic acid (0.223 g, 1.58 mmol), HATU (0.600 g, 1.58 mmol), and diisopropylethylamine (0.300 ml, 1.72 mmol) were added sequentially to a solution of 4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-yl amino)-piperidine-1-carboxylic acid tert-butyl ester (0.677 g, 1.44 mmol, prepared as described in Example 115) in a 6:1 mixture of CH2Cl2 and DMF (7 ml) at 25° C. The reaction mixture was stirred for 14 h at 25° C., then saturated NaHCO3 (7 ml) was added and the mixture was vigorously shaken by hand for 1 min. The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude 4-{1-benzenesulfonyl-5-[2-(3-methyl-isoxazol-4-yl)-acetylamino]-1H-pyrrolo[2,3-b]pyridin-4-ylamino}-piperidine-1-carboxylic acid tert-butyl ester as a brown oil. LCMS (Method G, ESI): RT=0.99 min, m+H=595.4. This material was used in the next step below without additional purification or characterization.

Provenance & Evidence