Trifluoroacetic acid → HCID 71280035, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-tert-butyl-2-(1-(cyclopropylmethyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 239 μmol) in dichloromethane (10 mL) under Ar, trifluoroacetic acid (744 mg, 0.50 mL, 6.53 mmol) was added at 25° C. After 18 h, the reaction was concentrated in vacuo to give a light brown residue. The residue was dissolved in a mixture of dichloromethane/methanol/NH3OH (3:2:0.25, 10.5 mL) and stirred at 25° C. After 2.5 h, the reaction was concentrated to give a yellow solid and dried in vacuo (200 mTorr, 25° C.). The solid was dissolved in ethanol (4.5 mL, 200 proof) and cooled to 4° C. After 18 h, the precipitated solid was isolated by filtration and dried in vacuo (200 mTorr, 40° C.) to give N-tert-butyl-2-(1-(cyclopropylmethyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (72.8 mg, 160 μmol, 66.9%) as a yellow solid. MS (M)'=455; 1H NMR (DMSO-d6) δ: 9.09 (s, 1H), 8.39 (s, 1H), 8.21 (d, J=2.3 Hz, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.88 (s, 1H), 7.40 (dd, J=2.3, 9.0 Hz, 1H), 7.20 (t, J=74.3 Hz, 1H), 5.86 (m, 1H), 5.08 (dd, J=1.5, 17.3 Hz, 2H), 4.63 (t, J=7.0 Hz, 2H), 2.71 (m, 2H), 1.51 (s, 9H).

Provenance & Evidence