CC-90003 is a covalent inhibitor of the ERK1 and ERK2 kinases. A scalable synthesis was required to manufacture drug substance for toxicological, drug product development, and clinical use. Significant selectivity issues involving substitution of a 2,4-dichloro-5-trifluoromethylpyrimidine, and safety issues arising from a nitration reaction employed to synthesize a 4-amino substituted pyridine were encountered. The solutions to these challenges resulted in a process capable of manufacturing multiple kilograms in good yield and high purity.

Selective, safe, scalable synthesis of a CC-90003, a covalent trifluoromethyl pyrimidine ERK 1&2 kinase inhibitor

254th National Meeting (2017)

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