Trifluoroacetic acid → 4-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide

Participants

Reaction Steps

To a solution of tert-butyl (1S,2R)-2-(5-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate (70 mg, 142 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (2.01 g, 1.35 mL, 17.6 mmol) and the mixture stirred at 25° for 2 h. The mixture was concentrated in vacuo and then diluted with dichloromethane and then washed successively with 1N NaOH (3×5 mL) and brine (5 mL). The organic phase was dried over sodium sulfate, concentrated in vacuo and then dried in vacuo to give 4-(6-(1H-pyrazol-1-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide (14.2 mg, 36.1 μmol, 25%) as a white solid. 1H NMR (DMSO-d6) δ: 11.93 (s, 1H), 8.63-8.71 (m, 1H), 8.45 (br. s., 1H), 7.78-7.94 (m, 3H), 7.71 (br. s., 1H), 7.51 (d, J=7.8 Hz, 1H), 7.05 (d, J=7.5 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 6.63 (dd, J=2.5, 1.8 Hz, 1H), 4.02 (br. s., 1H), 3.18 (br. s., 1H), 1.46-1.79 (m, 7H), 1.20-1.41 (m, 3H); MS (EI/CI) m/z: 394.3 [M+H].

Provenance & Evidence