Trifluoroacetic acid → HCID 71626044, compound

Participants

Reaction Steps

To a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-isopropyl-4-methylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (35 mg, 72.4 μmol) in dichloromethane (1.1 mL) was added trifluoroacetic acid (165 mg, 112 μL, 1.45 mmol) and the mixture stirred at room temperature for 20 h. The mixture was concentrated in vacuo and then the residue diluted with dichloromethane and a few drops of 25% aqueous NH4OH added until the mixture was measured at pH˜8. The mixture was then washed with water, the organic phase collected, concentrated in vacuo, and finally purified by chromatography (silica, 3 to 10% of a 99.5:0.5 methanol:NH4OH solution in dichloromethane) to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-isopropyl-4-methylpyridin-2-ylamino)pyridazine-3-carboxamide (15 mg, 39.1 μmol, 54%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.64 (s, 1H), 8.36 (s, 1H), 8.07 (s, 1H), 7.64 (s, 1H), 6.79 (d, J=4.3 Hz, 1H), 6.73 (s, 1H), 6.60 (s, 1H), 3.90 (s, 1H), 2.98 (m, 1H), 2.27 (s, 3H), 1.52-1.76 (m, 6H), 1.38 (m, 2H), 1.27 (d, J=7.0 Hz, 6H); MS (EI/CI) m/z: 384.1 [M+H].

Provenance & Evidence