Synthesis of Mavatrep: A Potent Antagonist of Transient
Receptor Potential Vanilloid‑1
Posted on 2015-11-20 - 00:00
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.
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Wells, Kenneth M.; Mehrman, Steven J.; Abdel-Magid, Ahmed F.; Ferraro, Caterina; Scott, Lorraine; Zhong, Hua Marlon; et al. (2016). Synthesis of Mavatrep: A Potent Antagonist of Transient
Receptor Potential Vanilloid‑1. ACS Publications. Collection. https://doi.org/10.1021/acs.oprd.5b00271
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AUTHORS (18)
KW
Kenneth M. Wells
SM
Steven J. Mehrman
AA
Ahmed F. Abdel-Magid
CF
Caterina Ferraro
LS
Lorraine Scott
HZ
Hua Marlon Zhong
CT
Christopher A. Teleha
SB
Scott Ballentine
XL
Xun Li
RR
Ronald K. Russell
JS
Jan M. Spink
CD
Craig Diamond
SY
Scott Youells
YZ
Yongzheng Zhang
FT
Fuh-Rong Tsay
SC
Sergio Cesco-Cancia
SM
Stephen M. Manzo
DB
Derek
A. Beauchamp