C[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O)N.C[C:13]1[CH:14]=[C:15](N=C=S)[CH:16]=[CH:17][C:18]=1[N+:19]([O-])=[O:20].OCCN.O=S(Cl)[Cl:31]>>[NH2:9][C:8]1([CH2:2][OH:20])[CH2:7][CH2:6][CH2:4][CH2:3]1.[ClH:31].[NH2:19][C:18]1([CH2:13][Cl:31])[CH2:17][CH2:16][CH2:15][CH2:14]13-Methyl-4-nitroaniline was converted to 3-methyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 3-methyl-4-nitrophenyl isothiocyanate according to Method C1a to give 2-(3-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(3-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane.
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