Trifluoroacetic acid → HCID 73295778, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-3-chloro-2-(3-methylisothiazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (40 mg, 80.8 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (184 mg, 124 μL, 1.62 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (1.5 mL), methanol (0.75 mL) and ammonium hydroxide (0.2 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with water and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-3-chloro-2-(3-methylisothiazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (15 mg, 37.0 μmol, 46%) as a dark orange solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.76 (s, 1H), 10.91 (s, 1H), 8.30 (d, J=3.2, 1 H), 7.33 (s, 1H), 7.13 (s, 1H), 2.42 (s, 3H), 1.62 (s, 9H); MS (EI/CI) m/z: 365.0 [M+H].

Provenance & Evidence