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

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-4-(4,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide (140 mg, 504 μmol) in NMP (2.52 mL) was added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (216 mg, 1.01 mmol) and the mixture heated at 130° C. for 72 h. The reaction mixture was cooled and diluted with ethyl acetate and brine. The organic phase was washed with brine (2×) and water (1×), then the organic phase was concentrated in vacuo then purified by chromatography (silica, 40-100% ethyl acetate in hexanes) to give tert-butyl (1S,2R)-2-(6-carbamoyl-5-(4,6-dimethylpyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (75 mg, 98.8 μmol, 20%) as an orange solid. MS (EI/CI) m/z: 456.2 [M+H].

Provenance & Evidence