(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → HCID 86689759, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-chloro-4-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazine-3-carboxamide (260 mg, 859 μmol) in N-methyl-2-pyrrolidinone (3.0 mL) was treated with tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (368 mg, 1.72 mmol), and the mixture was heated to 120° C. for 72 h. The solvent was evaporated under high vacuum and the residue was purified by chromatography (spherical silica 20-45 μM, 80 g, Versaflash Supelco, 0 to 5% of a 9:1 MeOH: NH4OH solution in CH2Cl2, 20 min) to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(1-methyl-1H-benzo[d]imidazol-4-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (132 mg, 32%) as a light brown foam. 1H NMR (CHLOROFORM-d) δ: 11.05 (s, 1H), 7.89 (d, J=2.6 Hz, 1H), 7.77 (s, 1H), 7.39 (br. s., 1H), 6.96-7.30 (m, 3H), 6.40 (br. s., 1H), 6.10-6.33 (m, 2H), 3.78 (br. s., 4H), 3.52 (br. s., 1H), 0.95-1.70 (m, 17H); LC-MS 481.0 [M+H]+.

Provenance & Evidence