Trifluoroacetic acid → N-isopropyl-2-(1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-isopropyl-2-(1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (113 mg, 227 mmol) in dichloromethane (3 mL) was added TFA (1.48 g, 1 mL, 13.0 mmol). The reaction mixture was stirred at 25° C. for 15 h then concentrated. The residue was re-dissolved in 5 mL of a solution of dichloromethane/MeOH/ammonium hydroxide; 60:10:1 and stirred at 25° C. for 3 h, then evaporated to a yellow solid. The solid was dissolved in dichloromethane (containing a few drops of MeOH) and purified by chromatography (40 g, 50 μm particle size, Analogix, 0 to 5% MeOH containing 10% ammonium hydroxide in dichloromethane, 15 min). The pure product was re-dissolved in MeOH and allowed to stand for solid formation. The solid was separated by decanting the mother liquors and then dried to give N-isopropyl-2-(1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (60 mg, 164 μmol, 72%) as a white needles. MS (M+H)+=367; 1H NMR (300 MHz, DMSO-d6) δ ppm 12.47-12.74 (m, 1H), 8.91 (s, 1H), 8.31 (s, 1H), 7.92 (d, J=8.31 Hz, 1H), 4.07-4.48 (m, 1H), 3.78 (s, 3H), 2.72 (s, 2H), 2.64 (t, J=6.42 Hz, 2H), 1.60 (t, J=6.42 Hz, 2H), 1.26 (d, J=6.42 Hz, 6H), 1.01 (s, 6H).

Provenance & Evidence