142885-91-4

Usage

Chemical Properties

Pale Yellow Solid

Uses

Impurity F from the synthesis of Omeprazole.

InChI:InChI=1/C16H16N4O3S/c1-9-7-17-14(10(2)15(9)20(21)22)8-24-16-18-12-5-4-11(23-3)6-13(12)19-16/h4-7H,8H2,1-3H3,(H,18,19)

Upstream product

• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 27231-36-3 5-methyl-1H-benzoimidazole-2-thiol 
• 1643-19-2 tetrabutylammomium bromide 
• 5197-95-5 benzyltriethylammonium bromide 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 

Downstream Products

• 73590-85-9 omeprazole sulfide 
• 317807-10-6 (S)-5-methoxy-2-[[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 

Relevant academic research and scientific papers

Inhibitors of the gastric H+, K+-atpase with enhanced therapeutic properties

Chemical syntheses and medical uses of novel inhibitors of the gastric H+, K+-ATPase for the treatment and/or management of duodenal ulcers, heartburn, acid reflux, other conditions mediated by gastric acid secretion and/or psoriasis are described.

Omeprazole synthesis

Omeprazole (VI) is made by the route:

Synthetic procedure for 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methylthio]-IH-benzimidazole hydrochloride and its conversion to omeprazole

The present invention relates to an efficient process for the preparation of 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylthio]-1-H-benzimidazole hydrochloride starting from 3,5-Lutidine and its conversion to Omeprazole (5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole) by selective oxidation with hydrogen peroxide.

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%.