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

Participants

Reaction Steps

To a stirred solution of 2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.34 mmol), EDCI (123 mg, 0.64 mmol), DMAP (110 mg, 0.90 mmol) and DIEA (131 mg, 1.02 mmol) in 6 mL of DMF was added tert-butyl 3-amino-3-methylpyrrolidine-1-carboxylate (100 mg, 0.54 mmol) in one portion at room temperature, then the mixture was stirred for 16 hours. The reaction mixture was poured into 40 mL of water, extracted with ethyl acetate (150 mL). The organic phase was evaporated at 40° C. under reduced pressure and the residue was triturated with petroleum ether then decanted and dried to give crude tert-butyl 3-methyl-3-(2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)pyrrolidine-1-carboxylate (76 mg, 47.0%) as a yellow solid. MS: (M+H)+=476.2.

Provenance & Evidence