Trifluoroacetic acid → HCID 71279672, compound

Participants

Reaction Steps

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide in dichloromethane (2 mL) was added drop-wise trifluoroacetic acid (1 mL) at room temperature and the reaction mixture was stirred for 2 hours. The solvent was removed 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: 38% acetonitrile/62% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 46% acetonitrile/54% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(3,4-dihydroxybutyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (30 mg, 39% over two steps) as a white solid. MS: (M+H)+=489.1; 1H NMR (300 MHz, DMSO): δ 12.85 (s, 1H), 9.11 (s, 1H), 8.42 (d, 1H, J=3.0 Hz), 8.24 (d, 1H, J=1.2 Hz), 7.92-7.88 (m, 2H), 7.45 (t, 1H, J=9.2 Hz), 7.23 (t, 1H, J=74.4 Hz), 4.67-4.64 (m, 2H), 3.48-3.26 (m, 4H), 2.16-2.10 (m, 4H), 1.86-1.83 (m, 4H), 1.54 (s, 9H).

Provenance & Evidence