Practical routes to the triarylsulfonyl chloride intermediate of a β3 adrenergic receptor agonist

Norihiro Ikemoto, Jinchu Liu, Karel M.J. Brands, James M. McNamara, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A β3 adrenergic receptor agonist was prepared on a multi-kilogram scale in high yield and purity via a convergent synthesis. A key intermediate in this synthesis was an arylthiazolylbenzenesulfonyl chloride. The triaryl segment of this sulfonyl chloride was assembled at the thiazole ring via coupling of α-haloketone and thiobenzamide precursors (Hantzsch synthesis). Three strategies for introducing the para-sulfonyl chloride moiety were developed and evaluated. The sulfonation/chlorination and diazotization/chlorosulfonylation routes were found the most efficient.

Original languageEnglish (US)
Pages (from-to)1317-1325
Number of pages9
JournalTetrahedron
Volume59
Issue number8
DOIs
StatePublished - Feb 17 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Sulfonyl chloride
  • Synthesis
  • β agonist

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