Trifluoroacetic acid → HCID 73295608, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(1-ethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (82 mg, 179 μmol) in dichloromethane (2.7 mL) was added trifluoroacetic acid (409 mg, 276 μL, 3.58 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.4 mL) and stirred at room temperature for 1 h. The reaction mixture was concentrated then purified by chromatography (silica, 15-65% dichloromethane/[10% dichloromethane/methanol/0.5% ammonium hydroxide]) to give N-tert-butyl-2-(1-ethyl-1H-pyrazol-4-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 101 μmol, 56%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.16 (s, 1H), 9.06 (s, 1H), 7.90 (d, J=3.3, 1 H), 7.85 (s, 1H), 7.84 (s, 1H), 7.73 (s, 1H), 7.59 (s, 1H), 4.08 (q, J=7.3, 2 H), 1.42 (s, 9H), 1.36 (t, J=7.3, 3 H); MS (EI/CI) m/z: 328.1 [M+H].

Provenance & Evidence