Trifluoroacetic acid → HCID 73295776, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 194 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (443 mg, 300 μL, 3.89 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated then purified by chromatography (silica, 5-8% methanol in dichloromethane) to give N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 122 μmol, 63%) as a light brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.13 (s, 1H), 8.44 (s, 1H), 7.91 (s, 1H), 7.87 (d, J=3.2, 1 H), 7.82 (s, 1H), 7.81 (s, 1H), 3.71 (s, 3H), 2.09 (s, 3H), 1.35 (s, 9H); MS (EI/CI) m/z: 328.1 [M+H].

Provenance & Evidence