Trifluoroacetic acid → N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (41.7 mg, 62.2 μmol) in dichloromethane (3 mL) under Ar trifluoroacetic acid (208 mg, 0.140 mL, 1.83 mmol) was added at 25° C. After 18 h, the reaction was concentrated in vacuo to give a yellow residue. The residue was dissolved in a mix of dichloromethane/methanol/NH3OH (3:2:0.25, 5.25 mL) and stirred at 25° C. After 2.5 h, the material was concentrated and dried in vacuo (200 mTorr, 40° C.) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(2-(4-methylpiperazin-1-yl)-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (22.4 mg, 41.4 mmol, 67%) as a yellow solid. MS (M)'=541; 1H NMR (DMSO-d6) δ: 12.84 (d, J=2.8 Hz, 1H), 9.02 (s, 1H), 8.41 (d, J=3.0 Hz, 1H), 8.23 (d, J=2.3 Hz, 1H), 7.89 (s, 1H), 7.75 (d, J=9.3 Hz, 1H), 7.41 (dd, J=2.3, 9.0 Hz, 1H), 7.21 (t, J=74.5 Hz, 1H), 5.71 (br. s, 2H), 3.82 (br. s, 2H), 3.50 (br. s, 2H), 2.74 (br. s, 2H), 2.67 (br. s, 2H), 2.33 (s, 3H), 1.51 (s, 9H).

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