Trifluoroacetic acid → HCID 73295781, compound

Participants

Reaction Steps

To a solution of tert-butyl 1-(3-(7-(tert-butylcarbamoyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)ethylcarbamate (150 mg, 257 mol) in dichloromethane (4 mL) was added trifluoroacetic acid (587 mg, 397 μL, 5.15 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 (0.7 mL) and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated then purified by chromatography (silica, 6-10% methanol/dichloromethane) to give 2-(3-(1-aminoethyl)phenylamino)-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (64 mg, 182 mol, 71%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 9.44 (s, 1H), 8.01 (s, 1H), 7.99 (d, J=7.9, 1 H), 7.98 (s, 1H), 7.77 (s, 1H), 7.22 (t, J=7.8, 1 H), 7.20 (s, 1H), 6.98 (d, J=7.8, 1 H), 4.05 (q, J=6.1, 1 H), 1.43 (s, 9H), 1.32 (d, J=6.5, 3 H); MS (EI/CI) m/z: 353.2 [M+H].

Provenance & Evidence