Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 26, Issue 3, Pages 568-582Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.1c00263
Keywords
Pictet-Spengler reaction; Buchwald-Hartwig C-N coupling; oligomers
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GDC-9545, a selective estrogen receptor degrader, is being developed as a treatment for ER+/HER2- breast cancer. A robust and efficient manufacturing process has been developed to produce GDC-9545.
GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545.tartrate.
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