Bromocyclopentane → 2-(4-Cyano-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

Participants

Reaction Steps

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 4-cyano-2-ethylphenyl isothiocyanate according to Method C1e to give 2-(4-cyano-2-ethylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(4-cyano-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The nitrile was hydrolyzed according to Method D9a to give 2-(4-carboxy-2-ethylphenylimino)-1-2-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The benzoic acid was reacted with dimethylamine according to Method D6b to afford 2-(4-(N,N-dimethylcarbamoly)-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Provenance & Evidence