C[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O)N.[CH3:12][C:13]1[CH:14]=[C:15]([N:22]=[C:23]=[S:24])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20].OCCN.Cl.Cl[CH2:31][C:32]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[OH:20][CH2:7][C:8]1([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:6]1.[CH3:12][C:13]1[CH:14]=[C:15]([N:22]=[C:23]2[S:24][CH2:31][C:32]3([CH2:36][CH2:35][CH2:34][CH2:33]3)[NH:37]2)[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]3-Methyl-4-nitroaniline was converted to 3-methyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 3-methyl-4-nitrophenyl isothiocyanate according to Method C1e to give 2-(3-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(3-methyl-4-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro [4.4]nonane.
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