Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]1>CN(C)C=O.C(OCC)(=O)C>[OH:20][C@H:17]1[CH2:18][CH2:19][C@H:14]([NH:13][C:2]2[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=2)[CH2:15][CH2:16]1To a solution of 6-chloro-5-nitronicotinonitrile (3.5 g) in N,N-dimethylformamide (35 ml) was added trans-4-aminocyclohexanol (4.39 g) at 0° C. The mixture was stirred at ambient temperature for 45 minutes under nitrogen atmosphere, and diluted with ethyl acetate. The resultant organic solution was washed with water (3 times) and brine, dried over magnesium sulfate, and concentrated in vacuo. The residual solid was washed with diethyl ether to give 6-(trans-4-hydroxycyclohexylamino)-5-nitronicotinonitrile (3.38 g) as a yellow solid.
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