Trifluoroacetic acid → HCID 71280256, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(6-chloroimidazo[1,5-a]pyridin-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (50 mg, 100 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (228 mg, 154 μL, 2.00 mmol) and the mixture stirred at room temperature. After 16 h the reaction mixture was concentrated, then the residue was redissolved in dichloromethane (2 mL), methanol (1 mL) and ammonium hydroxide (0.22 mL) and stirred at room temperature. After 2 h the reaction was concentrated in vacuo. The residue was purified by chromatography (silica, 30-100% of a 0.5:10:89.5 ammonium hydroxide:methanol:dichloromethane solution in dichloromethane). The collected material was concentrated, triturated with methanol and filtered to give N-tert-butyl-2-(6-chloroimidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (12 mg, 29.6 μmol, 30%) as a yellow solid. MS (M+H)+=369.1; 1H NMR (DMSO-d6) δ: 12.69 (s, 1H), 9.08 (s, 1H), 8.79 (s, 1H), 8.53 (s, 1H), 8.34 (d, J=9.7 Hz, 1H), 8.30 (s, 1H), 7.84 (s, 1H), 7.05 (d, J=9.7 Hz, 1H); 1.52 (s, 9H).

Provenance & Evidence