[C:1]([C:3]1S[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1)#N.[NH2:11][C:12]1[S:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1.[NH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1.[OH:25][CH2:26]CN.Cl.Cl[CH2:31][C:32]1(N)CCC[CH2:33]1>>[OH:25][CH2:26][C:5]1([NH2:8])[CH2:6][CH2:7][CH2:3][CH2:1]1.[C:17]([C:14]1[S:13][C:12]([N:11]=[C:20]2[S:21][CH2:22][C:23]3([CH2:24][CH2:33][CH2:32][CH2:31]3)[NH:19]2)=[CH:16][CH:15]=1)#[N:18]2-Cyano-5-nitrothiophene was reduced to 2-amino-5-cyanothiophene according to Method A1a. The aminothiophene was converted to 5-cyano-1-thiophene isothiocyanate according to Method A2b. 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 5-cyano-1-thiophene isothiocyanate according to Method C1e to give 2-(5-cyanothienylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give 2-(5-cyanothienylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane.
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