Pilot-Scale Synthesis of a Novel Non-Xanthine Adenosine A1 Receptor Antagonist. 1, 3-Dipolar Cycloaddition of Pyridine N-Imine to an Acetylene

…, N Hashimoto, R Uematsu, T Okamoto

Index: Zanka, Atsuhiko; Hashimoto, Norio; Uematsu, Ryoichi; Okamoto, Takumi Organic Process Research and Development, 1998 , vol. 2, # 5 p. 320 - 324

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Citation Number: 15

Abstract

Adenosine A1 receptor antagonist, FK838, has been synthesized in 44% overall yield by a five-step sequence which is operationally straightforward and readily carried out on a large scale. Investigations into the 1, 3-dipolar cycloaddition process that afforded a pyrazolo [1, 5- a] pyridine derivative are also described. Process improvements and optimization of each step permitted elimination of column chromatography, resulting in a practical and cost- ...