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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 4
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Original Articles

Improved Synthetic Approach to Tenatoprazole

, , &
Pages 576-582 | Received 30 Mar 2007, Published online: 27 Feb 2008
 

Abstract

An improved synthetic approach to tenatoprazole 1 is described. It started from 2,3,5‐trimethyl‐4‐nitropyridine‐N‐oxide 2 with acetic anhydride via rearrangement and hydrolysis to give 3, Chlorination with SOCl2 yielded 2‐chloromethyl‐3,5‐dimethyl‐4‐nitropyridine hydrochloride 4, then 4 condensed with 2‐mercapto‐5‐methoxy imidazole [4,5‐b]pyridine 5 to give 5‐methoxy‐2‐[(4‐nitro‐3,5‐dimethyl‐2‐pyridinyl)methylthio]imidazole[4,5‐b]pyridine 6. At last the title compound 1 was produced by two methods: 6 was oxidized with MCPBA and then methoxylated with CH3ONa to give 1 and 6 was first methoxylated with CH3ONa and then oxidized with MCPBA to give 1. The overall yield is around 26% for both five‐step syntheses.

Acknowledgment

The authors thank the management of Zhejiang Shangyu Sanhe Pharmachem Co., Ltd., for financial assistance. We also thank Yuanjiang Pan for his assistance on 1H NMR work.

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