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

Participants

Reaction Steps

2-(6-Chloro-1-(cyclopropylmethyl)-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (99 mg, 184 μmol) was dissolved in dichloromethane and to this was added trifluoroacetic acid (1.73 g, 1.17 mL, 15.2 mmol). After 72 h the mixture was concentrated in vacuo, the residue diluted in dichloromethane, and then and re-concentrated in vacuo. Purification by chromatography (silica, Analogix 40 g cartridge, 0-5% methanol in dichloromethane, gradient over 15 min) gave 2-(6-chloro-1-(cyclopropylmethyl)-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (15 mg, 36.7 μmol, 20.0%) as an off-white powder. MS (M+Na)+=431; 1H NMR (CDCl3) δ: 9.67 (br. s., 1H), 9.19-9.31 (m, 1H), 8.46 (d, J=8.7 Hz, 1H), 8.38 (d, J=3.0 Hz, 1H), 8.25 (d, J=7.9 Hz, 1H), 7.53 (d, J=1.1 Hz, 1H), 7.21-7.26 (m, 1H), 4.41-4.55 (m, 1H), 4.34 (d, J=7.2 Hz, 2H), 1.43 (d, J=6.4 Hz, 6H), 1.04-1.21 (m, 1H), 0.62-0.71 (m, 2H), 0.51 (q, J=4.9 Hz, 2H).

Provenance & Evidence