Bioorganic & Medicinal Chemistry Letters 2011-07-15

Synthesis of useful fragments in drug discovery: 2-Amino-5-tert-butylpyridine and its oxidised analogues.

Christopher G Thomson, John Reilly, David A Sandham

Index: Bioorg. Med. Chem. Lett. 21 , 4281-3, (2011)

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Abstract

A novel and robust synthesis of the fragment, 2-amino-5-tert-butylpyridine, has been described, which has been shown to have improved physicochemical properties over 4-tert-butylaniline, when considering drug-like properties. The synthesis also yields fragments containing more highly oxidised precursors to the tert-butyl group as intermediates. These fragments can be incorporated into final target molecules, yielding pharmaceutical compounds and their putative CYP-mediated oxidative metabolites, which can aid in elucidation of metabolic clearance processes.Copyright © 2011 Elsevier Ltd. All rights reserved.


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