Trifluoroacetic acid → HCID 178428271, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(3-methyl-1H-pyrazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (25 mg, 56.4 μmol) in dichloromethane (1 mL) was added trifluoroacetic acid (129 mg, 86.8 μL, 1.13 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 (1 mL), methanol (0.5 mL) and ammonium hydroxide (0.15 mL) and stirred at room temperature for 1 h. Purification by chromatography (silica, 20-50% [10% methanol/dichloromethane/0.5% ammonium hydroxide]/dichloromethane) gave N-tert-butyl-2-(3-methyl-1H-pyrazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (10 mg, 31.9 μmol, 57%) as a light brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.19 (s, 1H), 10.12 (s, 1H), 9.53 (s, 1H), 8.07 (s, 1H), 7.93 (d, J=3.0, 1 H), 7.81 (s, 1H), 6.33 (s, 1H), 2.19 (s, 3H), 1.45 (s, 9H); MS (EI/CI) m/z: 314.1 [M+H].

Provenance & Evidence