N-Acetyl-beta-alanine → 3-acetylamino-N-(1-benzenesulfonyl-4-cyclohexylamino-1H-pyrrolo[2,3-b]pyridin-5-yl)-propionamide

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3-Acetylaminopropionic acid (0.089 g, 0.675 mmol), HATU (0.256 g, 0.675 mmol), and diisopropylethylamine (0.141 ml, 0.840 mmol) were added sequentially to a solution of 1-benzenesulfonyl-N-4-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.250 g, 0.675 mmol) in CH2Cl2 (15 ml) at 25° C. The reaction mixture was stirred for 18 h at 25° C., then was partitioned between half-saturated NaHCO3 (100 ml) and EtOAc (2×125 ml). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with EtOAc (10 ml) to give a solid which was collected by filtration, washed with Et2O (10 ml), and air-dried to give 3-acetylamino-N-(1-benzenesulfonyl-4-cyclohexylamino-1H-pyrrolo[2,3-b]pyridin-5-yl)-propionamide as an off-white solid (0.183 g, 56%). LCMS (Method G, ESI): RT=0.82 min, m+H=484.3. This material was used in the next step below without additional purification or characterization.

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