Trifluoroacetic acid → N-tert-butyl-2-(6-fluoroimidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

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Reaction Steps

To a stirred solution of N-tert-butyl-2-(6-fluoroimidazo[1,5-a]pyridin-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (95 mg, 197 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (449 mg, 303 μL, 3.94 mmol) at room temperature. After 16 h the reaction was concentrated. The residue was dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL). After 1 h the reaction was concentrated. The residue was triturated with water and filtered. The solid was washed water and ether then dried under vacuum to give N-tert-butyl-2-(6-fluoroimidazo[1,5-a]pyridin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (64 mg, 182 μmol, 92%) as a yellow solid. MS: (M+H)+=353; 1H NMR (CD3OD) δ: 9.10 (s, 1H), 8.48 (d, J=5.1 Hz, 1H), 8.45 (s, 1H), 8.42 (m, 1H), 8.25 (s, 1H), 7.03 (m, 1H), 1.62 (s, 9H).

Provenance & Evidence