[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6](O)=[N:7][CH:8]=1)#[N:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[NH2:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]1>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([NH:25][C@H:26]2[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]2)=[N:7][CH:8]=1)#[N:2]To a solution of 5-cyano-2-hydroxy-3-nitropyridine (600 mg) in 6 mL of dichloromethane containing triethylamine(0.557 mL) was added methanesulfonyl chloride (0.295 mL) under stirring at 0° C. The reaction mixture was stirred at the same temperature for 30 minutes, and then trans-4-aminocyclohexanol (1.26 g) was added to the mixture at 0° C. After stirring at room temperature for 2 hours, the mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a preparative silica gel column chromatography eluting with 5% methanol in chloroform. The obtained substance was triturated with diisopropyl ether to give 5-cyano-2-(trans-4-hydroxycyclohexylamino)-3-nitropyridine (198.9 mg) as a yellow solid.
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