title: Solid-phase synthesis of trisubsituted guanidines.
abstract: The solid-phase library synthesis of trisubstituted guanidines was accomplished. Amines were loaded onto the 4-formyl-3,5-dimethoxyphenoxymethyl linker via reductive amination. Subsequent acylation with Fmoc-4-aminomethylbenzoic acid followed by Fmoc deprotection gave solid-supported primary amines. Alternatively, sulfonylation of resin-bound secondary amines with 4-cyanobenzenesulfonyl chloride followed by borane reduction also gave solid-supported primary amines. Both resins were acylated with isocyanates to furnish solid-supported ureas. Dehydration of ureas with p-toluenesulfonyl chloride in pyridine gave solid-supported carbodiimides. Nucleophilic addition of amines to the carbodiimide bond followed by cleavage off the solid support gave trisubstituted guanidines.
authors.affiliation: ChemRx Division, Discovery Partners International, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.
authors.forename: Thutam P
authors.initials: TP
authors.lastname: Hopkins
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Dener
authors.forename: Armen M
authors.initials: AM
authors.lastname: Boldi
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006146:Guanidines / Q000138:chemical synthesis*
chemical_list: D006146:Guanidines