Trifluoroacetic acid → HCID 71280197, compound

Participants

Reaction Steps

To a solution of 2-(1-(4-amino-4-methylpentyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (54 mg, 0.08 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-(1-(4-amino-4-methylpentyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide 2,2,2-trifluoroacetate (13 mg, 34%) as yellow solid. LCMS: (M+H)+=500; 1H NMR (300 MHz, CD3OD): δ 8.98 (s, 1H), 8.13 (s, 1H), 8.07 (d, 1H, J=2.1 Hz), 7.60 (d, 1H, J=9.3 Hz), 7.29 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.72 (t, 1H, J=74.1 Hz), 4.49-4.47 (m, 2H), 2.03-1.98 (m, 2H), 1.58-1.53 (m, 2H), 1.49 (s, 9H), 1.19 (s, 6H).

Provenance & Evidence