(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → tert-butyl (1S,2R)-2-(5-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxamide (90 mg, 284 μmol) in NMP (947 μL) was added tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (122 mg, 568 μmol) and the mixture heated to 140° C. for 16 h. Additional tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (61 mg, 284 μmol) was added and the mixture heated for a further 16 h. The reaction mixture was cooled, diluted with ethyl acetate and brine, then the phases were separated and the organic phase collected and washed with brine (2×). The organic layer was concentrated in vacuo then purified by chromatography (silica, 2-5% methanol in dichloromethane) to give a residue that was triturated with ethyl acetate, filtered, and washed with ether to give tert-butyl (1S,2R)-2-(5-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate (79 mg, 160 μmol, 56%) as a brown solid. MS (EI/CI) m/z: 495.1 [M+H].

Provenance & Evidence