Trifluoroacetic acid → N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Participants

Reaction Steps

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (105 mg, 0.138 mmol) in dichloromethane (4 mL) was added drop-wise trifluoroacetic acid (2 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-TLC (silica gel, EtOAc as eluent) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-(methylsulfonyl)propyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (50 mg, 72%) as a white solid. MS: (M+H)+=521.1; 1H NMR (300 MHz, DMSO): δ 12.85 (brs, 1H), 9.13 (s, 1H), 8.42 (s, 1H), 8.25 (s, 1H), 7.93 (t, 1H, J=7.8 Hz), 7.47 (d, 1H, J=9.0 Hz), 7.24 (s, 1H), 4.72 (d, 2H, J=6.6 Hz), 3.28-3.18 (m, 2H), 3.02 (s, 3H), 2.40-2.38 (m, 2H), 1.53 (s, 9H).

Provenance & Evidence