Carbodiimide-based benzimidazole library method

Richard D. Carpenter, Patrick B. Deberdt, Kit Lam, Mark J. Kurth

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Using carbodiimide reagents [1,3-diisopropylcarbodiimide or N-(3-dimethylaminopropyl)-N′'-ethylcarbodiimide hydrochloride (EDC)], we have developed a mild, generalized, one-pot method that delivers N-2-arylaminobenzimidazole esters from commercially available aryl isothiocyanates and o-phenylenediamines. Following saponification and acidifying, the benzimidazole acids were isolated in overall yields ranging from 75 to 88% from the starting aryl isothiocyanates. Nine benzimidazole acids were converted into a library consisting of 180 benzimidazole amides following EDC coupling with commercially available amines. The National Institute of General Medical Science will dispense these benzimidazole amides to academia groups for pilot scale biomedical studies. Using these mild conditions and environmentally safe reagents, we demonstrated that these pharmaceutically ornate heterocycles can also be constructed on solid support.

Original languageEnglish (US)
Pages (from-to)907-914
Number of pages8
JournalJournal of Combinatorial Chemistry
Volume8
Issue number6
DOIs
StatePublished - Nov 2006

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

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