Trifluoroacetic acid → HCID 71626970, compound

Participants

Reaction Steps

In a 25 mL round bottom flask, a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-cyclobutylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (112 mg, 233 μmol) in CH2Cl2 (5.0 mL) was treated with TFA (2.22 g, 1.5 mL, 19.5 mmol) and the mixture stirred to room temperature for 18 h. Solvents evaporated and residue purified by flash chromatography (spherical silica 20-45 μM, 80 g, Versaflash Supelco) eluting with 0 to 10% over 30 min (MeOH containing 10% NH4OH)/CH2Cl2 to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxamide (48 mg, 126 μmol, 54.1% yield) as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 11.43 (br. s., 1H), 8.45 (s, 1H), 8.03 (br. s., 1H), 7.51 (t, J=7.7 Hz, 1H), 6.75 (d, J=7.2 Hz, 1H), 6.68 (d, J=7.9 Hz, 1H), 5.62 (d, J=8.3 Hz, 1H), 5.37 (br. s., 1H), 3.88 (br. s., 1H), 3.65 (quin, J=8.5 Hz, 1H), 3.22 (d, J=4.9 Hz, 1H), 2.27-2.51 (m, 4H), 1.99-2.22 (m, 1H), 1.94 (dd, J=11.1, 5.5 Hz, 1H), 1.07-1.84 (m, 10H); LC-MS 382.0 [M+H]+.

Provenance & Evidence