The solid-phase Zincke reaction: preparation of omega-hydroxy pyridinium salts in the search for CFTR activation.
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.
Eda
M
M
Department of Chemistry, University of California, Davis 95616-5295, USA.
Kurth
M J
MJ
Nantz
M H
MH
D019005:Cystic Fibrosis Transmembrane Conductance Regulator / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011726:Pyridinium Compounds / Q000737:chemistry*
D011726:Pyridinium Compounds; D019005:Cystic Fibrosis Transmembrane Conductance Regulator