[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]=C=S)=[C:12]([CH3:19])[CH:11]=1)#[N:9].[OH:20]CCN.O=S(Cl)[Cl:26]>>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:19])[CH:11]=1)#[N:9].[NH2:1][C:2]1([CH2:3][OH:20])[CH2:7][CH2:6][CH2:5][CH2:4]1.[ClH:26].[NH2:1][C:2]1([CH2:3][Cl:26])[CH2:7][CH2:6][CH2:5][CH2:4]14-Cyano-2-methylaniline was synthesized as described in Method A1a. The aniline was converted to 4-cyano-2-methylphenyl 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 4-cyano-2-methylphenyl isothiocyanate according to Method C1a to give 2-(4-cyano-2-methylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2b to give 3-isobutyl-2-(4-iodo-2-methylphenylimino)-1-thia-3-azaspiro[4.4]nonane.
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