Pyrrolidine → N-(((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methylpiperidin-1-yl)(pyrrolidin-1-yl)-methylene)cyanamide

Participants

Reaction Conditions

Reaction Steps

To a solution of diphenyl cyanocarbonimidate (0.163 g, 0.685 mmol) and DIEA (0.239 mL, 1.371 mmol) in MeCN (5 mL) was added 1-((3R,4R)-4-methylpiperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (0.20 g, 0.68 mmol). The reaction was heated at about 80° C. for about 2 h. The reaction mixture was concd in vacuo. The residue was dissolved in pyrrolidine (1.0 mL, 12 mmol) and transferred to a sealed microwave vessel. The reaction was heated at about 120° C. for about 30 min in a CEM microwave. The reaction mixture was concd in vacuo and purified by RP-HPLC (Table 1, Method i) to give N-(((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methylpiperidin-1-yl)(pyrrolidin-1-yl)-methylene)cyanamide (0.030 g, 11%): LC/MS (Table 1, Method b) Rt=1.62 min; m/z: 377 (M+H)+

Provenance & Evidence