A new and efficient preparation of 2-aminothiazole-5-carbamides, applications to the synthesis of Dasatinib, a new potent pan-src kinase inhibitor

ORGN 933

Bang-Chi Chen, bangchi.chen@bms.com1, Rulin Zhao, rulin.zhao@bms.com2, Bei Wang2, Robert Droghini3, Jean Lajeunesse3, Pierre Sirard3, Masaki Endo3, Balu Balasubramanian, Balu.Balasubramanian@bms.com2, and Joel C Barrish, barrishj@bms.com2. (1) Bristol-Myers Squibb Pharmaceutical Research Institute, (2) Discovery Chemistry, Bristol-Myers Squibb Company, PO Box 4000, Princeton, NJ 08543-4000, (3) Process Research and Development, Bristol-Myers Squibb Company, Candiac, Quebec J5R11, Canada

A new and efficient method for the preparation of 2-aminothiazole-5-carbamides was developed using b-alkoxyacrylamides as the starting materials.  The reaction involves electrophilic a-bromination of b-alkoxyacrylamides followed by cyclization with thioureas to give functionalized 2-aminothiazole-5-carbamides in high yields.  This new method as well as its application to the synthesis of Dasatinib, a new potent pan-Src kinase inhibitor for the treatment of chronic myelogenous leukemia, will be presented.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007