Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

Collaborative work between Galderma R&D and Edelris yields new routes to the pyridin-2(1H)-one motif.

Efficient access to the 4-amino-3-carboxamide disubstituted pyridine-2(1H)-one kinase hinge-binder motif proved to be more challenging than anticipated requiring a significant investment in route scouting and optimization. This full paper focuses on the synthesis issues that we encountered during our route exploration and the original solutions we developed in order to identify two optimized library-style processes to prepare a large kinase inhibitor library.

Retrosynthetic disconnection of our privileged kinase scaffold 1.

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