A short and efficient synthesis of a complex heterocycle has been achieved. By controlling and differentiating the reactivity of seven nitrogen atoms, the aza-enriched core was assembled both chemo- and regio-selectively. This strategy resulted in an efficient 6 step linear synthesis of this architecturally complex clinical candidate. The subsequent process optimization delivered the intended commercial process, with significant cost reduction.

Taming down those nitrogens: Design and development of the commercial synthesis of a novel tyrosine kinase inhibitor

254th National Meeting (2017)

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