1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-3-methylcyclobutylcarbamate hydrochloride

Participants

Reaction Steps

A mixture of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.1 g, 0.32 mmol), tert-butyl 3-amino-3-methylcyclobutylcarbamate hydrochloride (0.1 g, 0.42 mmol), EDCI (0.092 g, 0.48 mmol), DMAP (0.059 g, 0.48 mmol), HOBT (0.065 g, 0.48 mmol) and DIPEA (0.248 g, 1.92 mmol) in 25 mL of DMF was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was passed through a pad of silica gel (200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1, v/v) to give tert-butyl 3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-3-methylcyclobutylcarbamate hydrochloride (0.11 g, 69%) as crude white solid which was used for the next step without further purification. MS: (M+H)+=494.2.

Provenance & Evidence