Trifluoroacetic acid → HCID 71604413, compound

Participants

Reaction Steps

To a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (91 mg, 188 μmol) in dichloromethane (2.9 mL) was added trifluoroacetic acid (429 mg, 290 μL, 3.76 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated in vacuo then diluted with NH4OH and dichloromethane. The mixture was washed with water, then the organic phase was concentrated in vacuo and purified by chromatography (silica, 3 to 15% methanol in dichloromethane) to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (46 mg, 120 μmol, 64%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59 (s, 1H), 8.34 (s, 1H), 8.08 (s, 1H), 7.63 (s, 1H), 6.80 (d, J=7.2 Hz, 1H), 6.70 (s, 1H), 6.60 (s, 1H), 3.88 (s, 1H), 3.25 (s, 1H), 2.67 (t, J=7.4 Hz, 1H), 2.26 (s, 3H), 1.71 (m, 2H), 1.54-1.71 (m, 6H), 1.35 (s, 2H), 0.93 (t, J=7.2 Hz, 3H); MS (EI/CI) m/z: 384.1 [M+H].

Provenance & Evidence