Practical and Scalable Synthesis of a Selective CCK1 Receptor Antagonist

…, L Gomez, S Shinde, JG Breitenbucher…

Index: Mapes, Christopher M.; Mani, Neelakandha S.; Deng, Xiaohu; Pandit, Chennagiri R.; McClure, Kelly J.; Pippel, Marna C. W.; Sehon, Clark A.; Gomez, Laurent; Shinde, Shirin; Breitenbucher, J. Guy; Jones, Todd K. Journal of Organic Chemistry, 2010 , vol. 75, # 22 p. 7950 - 7953

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Abstract

We describe a practical and scalable route to compound (Z)-1, a selective CCK1 receptor antagonist. Notable features of this concise route are (1) a regioselective construction of the pyrazole core through the reaction of an aryl hydrazine and an elaborated acetylenic ketone,(2) a Tf2O/pyridine mediated Z-selective dehydration of an α-hydroxyester, and (3) a stereoselective hydrolysis. The sequence is high-yielding and amenable for large-scale ...