Trifluoroacetic acid → 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (88 mg, 0.12 mmol) in 3 mL of dichloromethane was added trifluoroacetic acid (3 mL). The reaction mixture was stirred overnight at 25° C. 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-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate as yellow solid (9 mg, 13%). LCMS: (M+H)+=464; 1H NMR (300 MHz, CD3OD): δ 9.01 (s, 1H), 8.26 (s, 1H), 7.85 (s, 1H), 7.56 (d, 1H, J=9.0 Hz), 7.24 (dd, 1H, J1=9.0 Hz, J2=2.4 Hz), 4.15-4.12 (m, 5H), 1.87-1.84 (m, 4H), 1.59 (s, 9H), 1.27 (s, 6H).

Provenance & Evidence