A Scalable Route to the SMO Receptor Antagonist SEN826: Benzimidazole Synthesis via Enhanced in Situ Formation of the Bisulfite鈥揂ldehyde Complex
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- 作者：Matteo Betti ; Eva Genesio ; Guido Marconi ; Salvatore Sanna Coccone ; Paul Wiedenau
- 刊名：Organic Process Research & Development
- 出版年：2014
- 出版时间：June 20, 2014
- 年：2014
- 卷：18
- 期：6
- 页码：699-708
- 全文大小：531K
- 年卷期：v.18,no.6(June 20, 2014)
- ISSN：1520-586X
文摘
A practical and scalable route to the SMO antagonist SEN826 1 is described herein, including the discussion of an alternative approach to the synthesis of the target molecule. The optimized route consists of five chemical steps. A new and efficient access to the key intermediate 6 via the bisulfite鈥揳ldehyde complex was developed, significantly enhancing the yields and reducing costs. As a result, a synthetic procedure for preparation of multihundred gram quantities of the final product has been developed.