(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → HCID 86689756, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round bottom flask, a solution of 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxamide (281 mg, 925 μmol) in N-methyl-2-pyrrolidinone (3.5 mL) was treated with tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (397 mg, 1.85 mmol) and the mixture heated to 120° C. for 72 h. After cooling to room temperature the solvent was evaporated in high vacuum and residue was purified by flash column (spherical silica 20-45 μM, 80 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2 to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-cyclobutylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (112 mg, 25.1% yield) as a light brown foam. 1H NMR (CHLOROFORM-d) δ: 11.49 (br. s., 1H), 8.38 (s, 1H), 8.12 (d, J=3.0 Hz, 1H), 7.42 (t, J=7.9 Hz, 1H), 7.23 (s, 1H), 6.67 (d, J=7.2 Hz, 1H), 6.59 (d, J=7.9 Hz, 1H), 5.89-6.22 (m, 2H), 3.72-4.08 (m, 2H), 3.55 (quin, J=8.6 Hz, 1H), 1.76-2.11 (m, 4H), 1.19-1.74 (m, 19H); LC-MS 482.1 [M+H]+.

Provenance & Evidence