C([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])(C)(C)C.I[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15](C(C)(C)C)[CH:14]=1.NC1C=CC=CC=1.IC1C=CC(N=C=S)=C(C(C)(C)C)C=1.[OH:45]CCN.O=S(Cl)[Cl:51]>>[NH2:7][C:6]1([CH2:5][OH:45])[CH2:8][CH2:9][CH2:10][CH2:11]1.[ClH:51].[NH2:17][C:16]1([CH2:15][Cl:51])[CH2:14][CH2:13][CH2:19][CH2:18]12-tert-Butylaniline was converted to 4-iodo-2-tert-butylaniline according to Method A5a. The aniline was converted to 4-iodo-2-tert-butylphenyl isothiocyanate according to Method A2b. 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-iodo-2-tert-butylphenyl isothiocyanate according to Method C1a to give 2-(4-iodo-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 3-cyclopentyl-2-(4-iodo-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 3-cyclopentyl-2-(4-cyano-2-tert-butylphenylimino)-1-thia-3-azaspiro[4.4]nonane.
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