1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(3-methyloxetan-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

To a stirred solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (105 mg, 0.34 mmol) in 6 mL of DMF were added EDCI (128 mmol, 0.67 mmol), DMAP (82 mg, 0.67 mmol) and 3-methyloxetan-3-amine (44 mg, 0.50 mmol) in one portion at room temperature. Then the mixture was stirred for 16 hours. The solvent was evaporated at 70° C. under reduced pressure and the residue was triturated with water (10 mL), dichloromethane (10 mL), methanol (15 mL) then decanted and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(3-methyloxetan-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (50 mg, 38.9%) as a yellow solid. MS: (M+H)+=381; 1H NMR (300 MHz, DMSO): δ 12.90 (brs, 1H), 9.13 (s, 1H), 8.53-8.47 (m, 3H), 7.72 (d, 1H, J=7.8 Hz), 7.26-7.21 (m, 1H), 4.91 (d, 2H, J=6.0 Hz), 4.55 (d, 2H, J=6.3 Hz), 4.18 (s, 3H), 1.77 (s, 3H).

Provenance & Evidence