The solid-phase zincke reaction: Preparation of ω-hydroxy pyridinium salts in the search for CFTR activation

Masahiro Eda, Mark J. Kurth, Michael H. Nantz

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Abstract

A study of structural modifications of MPB-07 was undertaken as part of a synthetic program aimed at discovering small molecules with CFTR activation potential. Solid-phase synthesis techniques were used to prepare derivatives of MPB-07 employing the Zincke reaction for the construction of aromatic, quaternary ammonium salts such as those found in 2 or 3. In this transformation, primary amines react with highly electrophilic N-2,4-dinitrophenylpyridinium (DNP) salt 4 to afford pyridinium salt 8 with release of 2,4-dinitroaniline 6. Thus, the reaction of 1-(2,4-dinitrophenyl)pyridinium salts with various polymer-bound amino ethers, followed by cleavage from the resin, delivers the desired salts in good yield and high purity.

Original languageEnglish (US)
Pages (from-to)5131-5135
Number of pages5
JournalJournal of Organic Chemistry
Volume65
Issue number17
DOIs
StatePublished - Aug 25 2000

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ASJC Scopus subject areas

  • Organic Chemistry

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