104642-51-5Relevant articles and documents
The Solid-Phase Zincke Reaction: Preparation of ω-Hydroxy Pyridinium Salts in the Search for CFTR Activation
Eda, Masahiro,Kurth, Mark J.,Nantz, Michael H.
, p. 5131 - 5135 (2000)
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.
