Trifluoroacetic acid → HCID 71626099, compound

Participants

Reaction Steps

To a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (179 mg, 369 μmol) in CH2Cl2 (3.00 mL) was added TFA (1.48 g, 1.00 mL, 13.0 mmol) and mixture stirred to room temperature for 18 h. The solvent was evaporated and the residue purified by flash chromatography (spherical silica 20-45 μM, 23 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2 to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxamide (80 mg, 56.3% yield) as an off-white foam. 1H NMR (DMSO-d6) δ: 11.76 (s, 1H), 8.38 (br. s., 1H), 7.90 (s, 1H), 7.60-7.78 (m, 2H), 7.23 (d, J=7.6 Hz, 1H), 6.70-6.83 (m, 2H), 5.18 (s, 1H), 3.70 (br. s., 1H), 3.09 (br. s., 1H), 1.21-1.77 (m, 16H); LC-MS 386.1 [M+H]+.

Provenance & Evidence