Using Tandem Mass Spectrometry to Predict Chemical Transformations of 2-Pyrimidinyloxy- N-Arylbenzyl Amine Derivatives in Solution

Tandem mass spectrometry is used to predict the chemical transformations of 2-pyrimidinyloxy- N-arylbenzyl amine derivatives. Compound 1 , N-2-2-4,6- dimethoxypyrimidin-2-yloxy benzylamino phenyl benzamide was selected as a model to present our idea. The CID reactions of protonated 1 include an intr...

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Bibliographic Details
Published in:Journal of the American Society for Mass Spectrometry 2006-02, Vol.17 (2), p.253-263
Main Authors: Wang, Hao-Yang, Zhang, Xiang, Guo, Yin-Long, Tang, Qing-Hong, Lu, Long
Format: Article
Language:English
Subjects:
Benzamide
Benzylamines - analysis
CALCULATION METHODS
Chemical reactions
Chemistry
Crystallography, X-Ray
CUBIC LATTICES
Derivatives
Environmental Monitoring
Exact sciences and technology
Indicators and Reagents
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Ions
Mass spectrometry
MASS SPECTROSCOPY
MATHEMATICAL SOLUTIONS
Models, Molecular
MOLECULES
Organic chemistry
Pesticides - analysis
PHASE TRANSFORMATIONS
Phase transitions
REACTION KINETICS
Reaction mechanisms
Reactivity and mechanisms
Scientific imaging
Solutions
Spectrometry, Mass, Electrospray Ionization
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Spectroscopy
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Summary:Tandem mass spectrometry is used to predict the chemical transformations of 2-pyrimidinyloxy- N-arylbenzyl amine derivatives. Compound 1 , N-2-2-4,6- dimethoxypyrimidin-2-yloxy benzylamino phenyl benzamide was selected as a model to present our idea. The CID reactions of protonated 1 include an intramolecular S N 2 reaction and a cyclodehydration reaction. Under in-source CID conditions, deprotonated 1 undergoes a Smiles rearrangement reaction and then dissociates to the ion at m/z 349. Theoretical computations were invoked to shed light on the reaction mechanisms of 1 by the semiempirical PM3 method. These studies of gas-phase reactions show the reactivity of some potential reaction centers in this molecule, which inspired us to explore the solution phase analogous reactions of 1 . Further experiments show that 1 has two analogous reactions in acidic solution: the acid-catalyzed cyclodehydration reaction and the acid-catalyzed Smiles rearrangement reaction. Moreover, 1 undergoes the base-catalyzed Smiles rearrangement under basic conditions. The present study demonstrates that mass spectrometry can play an important role in predicting the chemical solution phase transformations of 2-pyrimidinyloxy- N-arylbenzyl amine derivatives.
ISSN:1044-0305
1879-1123
DOI:10.1016/j.jasms.2005.11.001