Trifluoroacetic acid → 2-(6-methyl-1H-indazol-3-yl)-N-(3-methylpyrrolidin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate

Participants

Reaction Steps

To a stirred solution of 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, 0.16 mmol) in 6 mL of dichloromethane was added trifluoroacetic acid (3 mL) in one portion at room temperature and stirred for one hour. The solvent was evaporated at 40° C. under reduced pressure and the residue was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 20% acetonitrile/80% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 45% acetonitrile/65% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give 2-(6-methyl-1H-indazol-3-yl)-N-(3-methylpyrrolidin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate (18 mg, 22.9%) as a white solid. MS: (M+H)+=376; 1H NMR (300 MHz, DMSO): δ 13.43 (s, 1H), 9.17 (s, 1H), 8.80 (brs, 1H), 8.49 (s, 1H), 8.38 (d, 1H, J=8.1 Hz), 8.29 (s, 1H), 7.47 (s, 1H), 7.16 (d, 1H, J=8.4 Hz), 3.94 (d, 1H, J=12.0 Hz), 3.51-3.20 (m, 3H), 2.57 (s, 3H), 2.30-2.17 (m, 2H), 1.70 (s, 3H).

Provenance & Evidence