Sodium Carbonate → HCID 68764850, compound

Participants

Reaction Steps

Crude N-(5-bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.200 g, 0.498 mmol, see Example 61), 3-(tert-butoxycarbonylamino)propanoic acid (0.189 g, 0.997 mmol), HOBT-H2O (0.107 g, 0.698 mmol) and EDCI (0.124 g, 0.648 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.434 mL, 2.49 mmol) was then added, and the reaction was allowed to stir 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 the crude residue. Purification by column chromatography (500:15 to 500:25 D CM: MeOH) gave tert-butyl 3-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.060 g, 21.0% yield).

Provenance & Evidence