Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714

Autor:	Joel M. Hawkins, Lulin Wei, Dennis E. Bourassa, Peter Robert Rose, Jeffery W. Raggon, A. Morgan Stewart, Heather N. Frost, James E. Phillips, Jennifer Lea Rutherford, Michael J. Castaldi, Barbara J. Sitter, Stephen S. Massett, Phillip J. Johnson, Michael G. Vetelino, Thomas Andrew Brandt, David H. Brown Ripin, Karin Neumann
Rok vydání:	2005
Předmět:	Olefin fiber chemistry.chemical_compound chemistry Drug candidate Heck reaction Organic Chemistry Sonogashira coupling Physical and Theoretical Chemistry Combinatorial chemistry Acetamide Allylamine
Zdroj:	Organic Process Research & Development. 9:440-450
ISSN:	1520-586X 1083-6160
Popis:	The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c5fded034f53a5be141f6f46ced0a248 https://doi.org/10.1021/op050039u Zobrazit plný text záznamu