Trifluoroacetic acid → HCID 73295780, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(2-(methylsulfonyl)pyridin-4-ylamino)-5-((2-(trimethylsilyl) ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (127 mg, 245 μmol) in dichloromethane was added trifluoroacetic acid (558 mg, 377 μL, 4.9 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (4 mL), methanol (2 mL) and ammonium hydroxide (0.7 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with water and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-2-(2-(methylsulfonyl)pyridin-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (94 mg, 242 μmol, 99%) as an off white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.51 (s, 1H), 10.36 (s, 1H), 8.39 (d, J=5.9, 1 H), 8.10 (s, 1H), 8.01 (s, 1H), 7.99 (dd, J=5.3, 2.3, 1 H), 7.83 (d, J=2.1, 1 H), 7.52 (s, 1H), 3.15 (s, 3H), 1.35 (s, 9H); MS (EI/CI) m/z: 389.1 [M+H].

Provenance & Evidence