(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxamide (134 mg, 438 μmol) in NMP (1.5 mL) was added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (376 mg, 1.75 mmol) in 3 portions approximately every 12 h over 36 h, with heating at 140° C. in the periods between additions. The mixture was then diluted with ethyl acetate and brine. The phases were separated and the organic phase washed twice with brine. The organic phase was concentrated in vacuo and then purified by chromatography (silica, 30 to 100% ethyl acetate in hexanes) to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4-methyl-6-propylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (91 mg, 188 μmol, 43%) as a light brown solid. MS (EI/CI) m/z: 484.3 [M+H].

Provenance & Evidence