Solid/solution phase annulation (SPAnTM) technology: Single-step derivatization of primary amines to piperazines on solid–phase

ORGN 419

Calum MacLeod, Blanca Martinez-Teipel, and Roland E. Dolle. Department of Chemistry, Adolor Corporation, 700 Pennsylvania Drive, Exton, PA 19341
Single–step amine annulation chemistries have been developed as part of the title technology platform to synthesize a range of cyclic amine derivatives. SPAnTM reagents I undergo microwave–assisted cyclization with primary amines to afford the corresponding resin–bound piperazines. Utilizing a standard Wang resin–linkage strategy, the piperazine products II become contaminated with linker–containing by–products under acidic cleavage. Employing a modified acid–labile Merrifield resin–linker, such contamination in products II is not observed.

 

Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004