Trifluoroacetic acid → HCID 71626972, compound

Participants

Reaction Steps

A solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (132 mg, 275 μmol) in CH2Cl2 (5 mL) was treated with TFA (4.08 g, 2.76 mL, 35.8 mmol) and the reaction mixture stirred to room temperature for 18 h. The solvent was evaporated and the residue purified by chromatography (spherical silica 20-45 μM, 80 g, Versaflash Supelco, 0 to 10% of a 9:1 MeOH:NH4OH solution in CH2Cl2, 30 min) to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazine-3-carboxamide (70 mg, 67%) as an off-white solid. 1H NMR (DMSO-d6) δ: 11.06 (s, 1H), 8.23 (br. s., 1H), 8.16 (s, 1H), 7.50 (br. s., 1H), 7.15-7.37 (m, 3H), 6.75 (s, 1H), 6.70 (d, J=7.6 Hz, 1H), 4.09 (br. s., 1H), 3.84 (s, 3H), 3.08 (br. s., 1H), 1.54 (br. s., 6H), 1.26 (d, J=17.0 Hz, 2H); LC-MS 381.1 [M+H]+.

Provenance & Evidence