142885-92-5

Basic information

• Product Name: 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide
• Synonyms: 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide;Omeprazole Sulfide N-Oxide;4-methoxy-2-(((5-methoxy-1H-benzo[d]imidazol-2-yl)thio)methyl)-3,5-dimethylpyridine 1-oxide;Omeprazole Impurity 26;5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole;Ufiprazole Impurity 1
• CAS NO: 142885-92-5
• Molecular Formula: C₁₇H₁₉N₃O₃S
• Molecular Weight: 345.41606
• Product Categories: Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 142885-92-5.mol

Chemical Properties

• Melting Point: 186-188 °C
• Boiling Point: 632.6±65.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly), Methanol (Sl
• PKA: 9.42±0.10(Predicted)
• CAS DataBase Reference: 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide(142885-92-5)
• EPA Substance Registry System: 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide(142885-92-5)

Safety Data

• Hazardous Substances Data: 142885-92-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide is used as a metabolite of Omeprazole for the treatment of various ulcerative conditions. Its role in the metabolism of Omeprazole contributes to the drug's efficacy in reducing gastric acid production, thereby alleviating symptoms and promoting healing of ulcers.
Used in Research and Development:
5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide can be utilized in research and development for the study of proton pump inhibitors and their metabolites. Understanding the properties and interactions of 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide can provide insights into the mechanisms of action of Omeprazole and potentially lead to the development of new antiulcerative agents or other therapeutic applications.
Used in Drug Metabolism Studies:
5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide serves as a valuable compound for studying drug metabolism pathways. By examining how 5-Methoxy-2-[[(4-Methoxy-3,5-diMethyl-2-pyridinyl)Methyl]thio]-1H-benziMidazole N-Oxide is processed and eliminated from the body, researchers can gain a better understanding of the metabolic processes involved in the breakdown and clearance of proton pump inhibitors and other related drugs.

Upstream product

• 848694-10-0 2-chloromethyl-3,5-dimethyl-4-methoxypyridine-N-oxide 
• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 142885-90-3 5-METHOXY-2-((3,5-DIMETHYL-4-NITRO-2-PYRIDINYL-N-OXIDE)-METHYLTHIO)-1H-BENZIMIDAZOLE 
• 75-09-2 dichloromethane 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 

Downstream Products

• 73590-58-6 omeprazole 

Relevant articles and documents

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.

A process for the preparation of omeprazol

The process starts by reacting 2,3,5 trimethylpyridine with hydrogen peroxide in the presence of catalysts, giving new reactive ionic species allowing the number of required steps to be substantially reduced. In the final important step, oxidation to omeprazol, there are used new salts of 5-methoxy-2-((3,5-dimethyl-4-methoxy-2-pyridine)methylthio)-1H-benzimidazole which, as the oxidation evolves, precipitate the omeprazol. The new oxidation method avoids superoxidations, provide for faster oxidation, high purity and yields of over 90%.