1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyanomethyl-methyl-amide

Participants

Reaction Steps

A solution of 5-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid (0.060 g, 0.18 mmol), methylaminoacetonitrile (0.200 mL, 1.64 mmol) and EDCI (0.315 g, 1.64 mmol) in 3 mL of ethanol and 3 mL of dichloromethane was stirred for 1 h, then concentrated. The resulting residue was partitioned between 30 ml of ethyl acetate and 30 mL of a 10% citric acid solution, and the aqueous layer was extracted 30 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->40% EtOAc/hexanes) afforded 0.040 g (58%) of 5-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid cyanomethyl-methyl-amide as a pale yellow solid.

Provenance & Evidence