Methanol → 2-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide

Participants

Reaction Steps

4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.30 g, 0.976 mmol, see Example 25), 2-(benzyloxy)acetic acid (0.195 g, 1.17 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP—C1”; 0.298 g, 1.17 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.680 mL, 4.88 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with MeOH (5 mL), and 3M LiOH (0.5 mL) was added and stirred for 10 minutes. 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 (500:10-500:20 DCM:MeOH) to give 2-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.22 g, 49.4% yield).

Provenance & Evidence