Evolution of the process strategies to prepare CEP-28122, an ALK inhibitor, is presented. The initial medicinal chemistry route, used for the preparation of key supplies for biological screening, is reviewed. In addition, the process research and development of the final optimized process for manufacture of preclinical and clinical supplies is discussed. Details regarding a blocking group strategy for selective nitration; discovery of a one-pot transfer hydrogenation to effect a reductive amination, nitro group reduction and dehalogenation; an enzymatic resolution of a critical intermediate and the discovery of a novel, stable, in situ generated mixed mesylate hydrochloride salt of the API are disclosed.

Development and scale-up of an optimized route to the ALK inhibitor CEP-28122

244th National Meeting (2012)

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