Trifluoroacetic acid → HCID 73295614, compound

Participants

Reaction Steps

N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 174 μmol) was dissolved in dichloromethane (3 mL) and treated with trifluoroacetic acid (396 mg, 268 μL, 3.48 mmol). After stirring at room temperature for 16 h, the mixture was concentrated in vacuo then re-dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.35 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then diluted with water, triturated and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg, 168 μmol, 97%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.55 (s, 1H), 10.12 (s, 1H), 8.19 (d, J=2.8, 1 H), 8.16 (s, 1H), 7.95 (d, J=8.8, 2 H), 7.88 (d, J=8.8, 2 H), 7.75 (s, 1H), 3.22 (s, 3H), 1.54 (s, 9H); MS (EI/CI) m/z: 388.2 [M+H].

Provenance & Evidence