Trifluoroacetic acid → HCID 71279888, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-4-methylpentylcarbamate (75 mg, 0.15 mmol) in 6 mL of dichloromethane was added trifluoroacetic acid (3 mL) in one portion at room temperature and the solution stirred for 2 hours. 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/55% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give N-(5-amino-2-methylpentan-2-yl)-2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate (35 mg, 58%) as a pale yellow solid. MS: (M+H)+=410; 1H NMR (300 MHz, DMSO): δ 12.98 (s, 1H), 9.11 (s, 1H), 8.49-8.42 (m, 2H), 7.88 (s, 1H), 7.74 (d, 1H, J=9.9 Hz), 7.60 (brs, 3H), 7.20 (t, 1H, J=9.0 Hz), 4.18 (s, 3H), 2.76 (brs, 2H), 2.00-1.94 (m, 2H), 1.61 (brs, 2H), 1.25 (s, 6H).

Provenance & Evidence