Practical routes to the triarylsulfonyl chloride intermediate of a β3 adrenergic receptor agonist |
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Authors: | Norihiro Ikemoto Jinchu LiuKarel MJ Brands James M McNamaraPaul J Reider |
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Institution: | Department of Process Research, Merck and Co. Inc., R800-C267, P.O. Box 2000, Rahway, NJ 07065-0900, USA |
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Abstract: | A β3 adrenergic receptor agonist was prepared on a multi-kilogram scale in high yield and purity via a convergent synthesis. A key intermediate in this synthesis was an arylthiazolylbenzenesulfonyl chloride. The triaryl segment of this sulfonyl chloride was assembled at the thiazole ring via coupling of α-haloketone and thiobenzamide precursors (Hantzsch synthesis). Three strategies for introducing the para-sulfonyl chloride moiety were developed and evaluated. The sulfonation/chlorination and diazotization/chlorosulfonylation routes were found the most efficient. |
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Keywords: | β3 agonist synthesis sulfonyl chloride |
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