Trifluoroacetic acid → HCID 73295443, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(p-tolylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (80 mg, 176 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (402 mg, 272 μL, 3.53 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 mixture was concentrated and triturated with water. The solid was collected by filtration and washed with water and ether. Purification by chromatography (silica, 20-40% of a 10:89.5:0.5 methanol:dichloromethane:ammonium hydroxide solution in dichloromethane) gave N-tert-butyl-2-(p-tolylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (17 mg, 52.6 μmol, 30%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.26 (s, 1H), 9.34 (s, 1H), 7.97 (s, 1H), 7.96 (d, J=3.3, 1 H), 7.76 (s, 1H), 7.57 (t, J=8.5, 2 H), 7.09 (d, J=8.1, 2 H), 2.26 (s, 3H), 1.44 (s, 9H); MS (EI/CI) m/z: 324.1 [M+H].

Provenance & Evidence