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Parallel iterative solution-phase synthesis of 5-amino-1-aryl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid amide derivatives

✍ Scribed by Bernd Brodbeck; Bernd Püllmann; Sébastien Schmitt; Matthias Nettekoven

Book ID
104253002
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
289 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The parallel iterative solution-phase synthesis of 5-amino-1-aryl- [1,2,4]triazolo [1,5-a]pyridine-7-carboxylic acid amide derivatives is described. The key intermediate 2,6-bis-aminopyridine-4-carboxylic acid methyl ester was synthesised in a two step procedure in 64% overall yield and elaborated to a variety of triazolopyridine-5-carboxylic acid methyl ester by selective pyridine-N-amination, condensation of the adduct with a wide selection of aldehydes and subsequent cyclisation and oxidation. The desired esters were obtained in yields up to 70%. The final transformation to the amide derivatives was accomplished by application of carefully optimised reaction conditions thus giving access to a library of total 500 triazolopyridine amide derivatives. Iterative synthetic cycles (12-48 library members each) allowing for maximal flexibility in chemistry and maximal efficiency in in vitro biological activity optimisation guided by molecular modelling efforts constitute a synergistic procedure for rapid lead optimisation.

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