Trifluoroacetic acid → HCID 73295775, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(3-methyl-1,2,4-thiadiazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (128 mg, 277 μmol) in dichloromethane (4.3 mL) was added trifluoroacetic acid (632 mg, 427 μL, 5.55 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (4 mL), methanol (2 mL) and ammonium hydroxide (0.6 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-2-(3-methyl-1,2,4-thiadiazol-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 272 μmol, 98%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.80 (s, 1H), 12.57 (s, 1H), 8.35 (s, 1H), 8.34 (s, 1H), 7.34 (s, 1H), 2.53 (s, 3H), 1.62 (s, 9H); MS (EI/CI) m/z: 332.1 [M+H].

Provenance & Evidence