Evaluation of kilogram-scale Sonagashira, Suzuki, and Heck coupling routes to Oncology candidate CP-724,714

…, J Hawkins, PJ Johnson, SS Massett…

Index: Ripin, David H. Brown; Bourassa, Dennis E.; Brandt, Thomas; Castaldi, Michael J.; Frost, Heather N.; Hawkins, Joel; Johnson, Phillip J.; Massett, Stephen S.; Neumann, Karin; Phillips, James; Raggon, Jeffery W.; Rose, Peter R.; Rutherford, Jennifer L.; Sitter, Barbara; Stewart III, A. Morgan; Vetelino, Michael G.; Wei, Lulin Organic Process Research and Development, 2005 , vol. 9, # 4 p. 440 - 450

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Citation Number: 63

Abstract

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 ...