(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → HCID 86689785, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(6-isopropyl-5-methoxypyridin-2-ylamino)pyridazine-3-carboxamide (199 mg, 618 μmol) in NMP (2.06 mL) was added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (532 mg, 2.47 mmol) in four portions approximately every 12 h while heating at 140° C. After a total heating time of 48 h, the mixture was cooled, diluted with ethyl acetate and brine, then the phases were separated and the organic phase washed twice more with brine. The organic phase was concentrated in vacuo then purified by chromatography (silica, 1 to 5% methanol in dichloromethane) to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-isopropyl-5-methoxypyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (100 mg, 200 μmol, 32%) as a brown solid. MS (EI/CI) m/z: 500.4 [M+H].

Provenance & Evidence