Process development for the synthesis of an advanced heterocyclic intermediate in the preparation of a retinoic acid receptor-related orphan receptor gamma/C (RORc) ligand will be described. Reaction conditions and workup/isolation methods for the key triazole formation were explored to control the purity and increase the yield of the product. Different free basing methods were implemented at several stages due to the challenging solubility profiles of the associated compounds. The improved synthetic process resulted in more robust and more efficient manufacture of a high-quality nitrogen rich building block on kilogram scale.

Improved synthesis of a nitrogen rich heterocyclic intermediate toward a RORc ligand

254th National Meeting (2017)

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