1401466-58-7Relevant articles and documents
Early Development Scale-Up of a Structurally-Challenging 5-Lipoxygenase Activating Protein (FLAP) Inhibitor
Mulder, Jason A.,Gao, Joe,Fandrick, Keith R.,Zeng, Xingzhong,Desrosiers, Jean-Nicolas,Patel, Nitinchandra D.,Li, Zhibin,Rodriguez, Sonia,Lorenz, Jon C.,Wang, Jun,Ma, Shengli,Fandrick, Daniel R.,Grinberg, Nelu,Lee, Heewon,Bosanac, Todd,Takahashi, Hidenori,Chen, Zhidong,Bartolozzi, Alessandra,Nemoto, Peter,Busacca, Carl A.,Song, Jinhua J.,Yee, Nathan K.,Mahaney, Paige E.,Senanayake, Chris H.
, p. 1427 - 1434 (2017)
A practical and efficient synthesis of the FLAP inhibitor 1 was developed addressing multiple scale-up and safety concerns posed by the established synthesis and utilized a resolution strategy (replacing supercritical fluid chromatography (SFC) separation) for expedient access to the key structural component of 1: the challenging chiral quaternary center. Also highlighted are in situ IR monitoring, condensation to form the 1,2,4-oxadiazole ring, and an efficient Suzuki-Miyaura coupling.