Synthesis of Mavatrep: A Potent Antagonist of Transient Receptor Potential Vanilloid-1

Autor:	Yongzheng Zhang, Stephen M. Manzo, Derek A. Beauchamp, Sergio Cesco-Cancia, Xun Li, Ahmed F. Abdel-Magid, Fuh-Rong Tsay, Scott A. Ballentine, Caterina Ferraro, Kenneth M. Wells, Christopher A. Teleha, Hua Marlon Zhong, Scott Youells, Steven J. Mehrman, Ronald K. Russell, Lorraine Scott, Jan M. Spink, Craig Diamond
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Transient receptor potential channel Trifluoromethyl Suzuki reaction Process development Chemistry Stereochemistry Yield (chemistry) Organic Chemistry TRPV1 Antagonist Imidazole Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 19:1774-1783
ISSN:	1520-586X 1083-6160
DOI:	10.1021/acs.oprd.5b00271
Popis:	The process development of Mavatrep (1), a potent transient receptor potential vanilloid-1 (TRPV1) antagonist, is described. The two key synthetic transformations are the synthesis of (E)-6-bromo-2-(4-(trifluoromethyl)styryl)1H-benzo[d]imidazole (4) and the Suzuki coupling of 4 with 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (5). Compound 1a was prepared in four chemical steps in 63% overall yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8d85dfd2095f7bcb55164604dce960af https://doi.org/10.1021/acs.oprd.5b00271 Zobrazit plný text záznamu