Cyanoacetic acid → HCID 59540533, compound

Participants

Reaction Steps

Dichloromethane (1 mL) was added to a mixture of EDCI (0.181 g, 0.945 mmol), HOBT monohydrate (0.128 g, 0.945 mmol), cyanoacetic acid (0.060 g, 0.71 mmol), and 2,2-Dimethyl-1-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.1718 g, 0.473 mmol) under argon. Diisopropylethylamine (DIPEA, 0.41 mL; 0.304 g, 2.36 mmol) was subsequently added and the reaction was stirred overnight at ambient temperature. The reaction was quenched with saturated aqueous NaHCO3 and extracted 3 times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Preparative thin layer chromatography afforded 0.0402 g (20% yield) of 3-(4-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-3-oxo-propionitrile as an off-white solid.

Provenance & Evidence