Trifluoroacetic acid → HCID 71279946, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-((2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamido)methyl)-3-hydroxyazetidine-1-carboxylate (86 mg, 0.16 mmol) in 3 mL of dichloromethane was added 3 mL of trifluoroacetic acid. The reaction mixture was stirred overnight at room temperature. After solvent evaporation, 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 are: 40% acetonitrile/60% water (0.1% trifluoroacetic acid V/V) initially, and then proceed to 50% acetonitrile/50% water (0.1% trifluoroacetic acid V/V) in a linear fashion after just 9 min) to afford 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-((3-hydroxyazetidin-3-yl)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide trifluoroacetate (6 mg, 9%) as yellow solid. LCMS: (M+H)+=396; 1H NMR (300 MHz, CD3OD): δ 9.05 (s, 1H), 8.48-8.42 (m, 1H), 8.23 (s, 1H), 7.20 (d, 1H, J=9.0 Hz), 6.99 (t, 1H, J=9.3 Hz), 4.10-3.89 (m, 6H).

Provenance & Evidence