Sodium Carbonate → (R)-tert-butyl 1-(4-(3-acetamido-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

Crude N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.050 g, 0.15 mmol, see Example 52), (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.0496 g, 0.166 mmol), HOBT-H2O (0.0323 g, 0.211 mmol), and EDCI (0.0375 g, 0.196 mmol) were placed in DCM (5 mL). DIEA (d 0.742; 0.131 mL, 0.752 mmol) was then added, and the reaction was stirred for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:13-500:18 DCM:MeOH) to give (R)-tert-butyl 1-(4-(3-acetamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.047 g, 57.7% yield).

Provenance & Evidence