Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10].Cl.[CH3:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]1[NH2:20].[CH:21](N(CC)C(C)C)(C)C>CC(O)C>[CH3:21][N:20]([C@H:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[CH3:13])[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10]In a microwave reaction vessel 4-chloro-3-nitro-2-pyridinamine (70 mg) and (1S,2R)-2-methylcyclohexanamine hydrochloride (66 mg) were suspended in 2-propanol (0.35 mL). To the mixture was added N,N-diisopropylethylamine (0.21 mL). The vessel was sealed and reacted in the microwave reactor at 130° C. for 1hour. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give N4-methyl-N4-[(1S,2R)-2-methylcyclohexyl]-3-nitro-2,4-pyridinediamine (75 mg) as a yellow amorphous.
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