Trifluoroacetic acid → N-tert-butyl-2-(3-(1-hydroxyethyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

N-tert-Butyl-2-(3-(1-hydroxyethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (143 mg, 296 mol) was dissolved in dichloromethane (4.5 mL) and treated with trifluoroacetic acid (674 mg, 456 μL, 5.91 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (4 mL), methanol (3 mL) and ammonium hydroxide (0.7 mL) and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated then purified by chromatography (silica, methanol in dichloromethane) gave N-tert-butyl-2-(3-(1-hydroxyethyl)phenylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (55 mg, 156 μmol, 53%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.29 (s, 1H), 9.44 (s, 1H), 8.00 (s, 1H), 7.99 (s, 1H), 7.98 (d, J=2.8, 1 H), 7.78 (s, 1H), 7.19 (m, 2H), 6.91 (d, J=7.5, 1 H), 5.17 (d, J=4.0, 1 H), 4.70 (m, 1H), 3.38 (q, J=7.2, 1 H), 1.43 (s, 9H), 1.34 (d. J=6.3, 3 H), 1.09 (t, J=7.2, 1 H); MS (EI/CI) m/z: 354.2 [M+H].

Provenance & Evidence