Trifluoroacetic acid → 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-ethoxypyridin-2-ylamino)pyridazine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (1S,2R)-2-(6-carbamoyl-5-(6-ethoxypyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (32.2 mg, 51.2 μmol) was dissolved in dichloromethane (1 mL) and treated with trifluoroacetic acid (744 mg, 0.5 mL, 6.53 mmol). The reaction was stirred at 25° C. for 3 h then concentrated in vacuo to a brown oil. This oil was dissolved in dichloromethane, washed with 1N NaOH (3×5 mL) and brine (5 mL), then the organic phase was dried (Na2SO4), filtered and concentrated to give an off-white solid. The solid was triturated with Et2O (3×5 mL) and dried overnight in vacuo to give an off-white solid, 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-ethoxypyridin-2-ylamino)pyridazine-3-carboxamide (12.6 mg, 33.6 μmol, 66% yield), 1H NMR (DMSO-d6) δ: 11.65 (br. s., 1H), 8.40 (br. s., 1H), 7.71 (s, 1H), 7.64 (t, J=7.9 Hz, 2H), 6.77 (d, J=7.8 Hz, 1H), 6.54 (d, J=7.8 Hz, 1H), 6.36-6.42 (m, 1H), 4.35 (q, J=7.0 Hz, 2H), 3.85 (br. s., 1H), 3.09 (br. s., 1H), 1.48-1.74 (m, 6H), 1.20-1.40 (m, 5H); MS (EI/CI) m/z: 372.3 [M+H].

Provenance & Evidence