953787-51-4

Usage

Uses

Used in Pharmaceutical Industry:
5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole-N-oxide is used as an impurity in the synthesis of Pantoprazole for the treatment of gastrointestinal conditions.
5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole-N-oxide is relevant in the context of pharmaceutical manufacturing, where the synthesis of Pantoprazole may inadvertently produce this impurity. It is important to monitor and control the presence of such impurities to ensure the safety, efficacy, and quality of the final drug product.

InChI:InChI=1/C16H15F2N3O4S/c1-23-13-5-6-21(22)12(14(13)24-2)8-26-16-19-10-4-3-9(25-15(17)18)7-11(10)20-16/h3-7,15H,8H2,1-2H3,(H,19,20)

Upstream product

• 953787-47-8 2-chloromethyl-3,4-dimethoxypyridine-N-oxide 
• 97963-62-7 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole 
• 72830-09-2 2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride 

Downstream Products

• 953787-55-8 5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 
• 102625-70-7 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole 

Relevant academic research and scientific papers

Method for preparing pantoprazole nitrogen oxide

The invention provides a preparation method of pantoprazole nitrogen oxide, which is implemented according to the following steps: reacting 2-chloromethyl-3, 4-dimethoxypyridine hydrochloride servingas a raw material with m-chloroperoxybenzoic acid, and carrying out oxidization to prepare pyridine nitrogen oxide; and enabling the pyridine nitrogen oxide to react with 5-difluoromethoxy-2-mercapto-1H-benzimidazole to generate 5-difluoromethoxy-2-[(3, 4-dimethoxy-2-pyridyl) methyl] thio-1H-benzimidazole nitrogen oxide. The genetically toxic impurity pantoprazole nitrogen oxide of the pantoprazole sodium sesquihydrate is prepared by an economical and green method, the operation is simple and convenient, the condition is mild, and the product purity is high.

Efficient synthesis of N-Oxide derivatives: Substituted 2-(2-(pyridyl-N-oxide)methylsulphinyl)benzimidazoles

Different substituted 2-chloromethylpyridyl derivatives (6a-d) were oxidized with mCPBA to give the respective 2-chloromethylpyridine-N-oxide derivatives (7a-d) at low temperature, which on condensation with 2-mercapto-1H-benzimidazole (8a-c) in the presence of aprotic solvents give the 2-[[(pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole (9a-d) in good yield. Finally, 9a-d oxidized with mCPBA in chlorinated solvent gives a mixture of 2-[[(pyridin-2-yl-1-oxide)methyl]sulfonyl]-1H-benzimidazole (3a-d, 10%) and 2-[[(pyridin-2-yl-1-oxide) methyl]sulfinyl]-1H-benzimidazole (4a-d, 90%) derivatives. Copyright Taylor & Francis Group, LLC.