924663-37-6

Basic information

• Product Name: Rebeprazole sulfone N-oxide
• Synonyms: 2-[[[4-(3-Methoxypropoxy)-3-methyl-1-oxido-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazol;Rabeprazole Sulfone N-Oxide;Rebeprazole sulfone N-oxide;1H-Benzimidazole, 2-[[[4-(3-methoxypropoxy)-3-methyl-1-oxido-2-pyridinyl]methyl]sulfonyl]-;2-[[[4-(3-Methoxypropoxy)-3-methyl-1-oxido-2-pyridinyl]methyl]sulfonyl]-1H-benzimidazole;Rabeprazole IMpurity-sulphone N-Oxide;Rabeprazole IMpurity B;Rabeprazole EP Impurity I
• CAS NO: 924663-37-6
• Molecular Formula: C18H21N3O5S
• Molecular Weight: 391.44
• Product Categories: Rabeprazole;Impurities & Metabolites;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 924663-37-6.mol

Chemical Properties

• Melting Point: 153-156 °C
• Boiling Point: 696.922°C at 760 mmHg
• Flash Point: 375.285°C
• Appearance: /
• Density: 1.36
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Rebeprazole sulfone N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Rebeprazole sulfone N-oxide(924663-37-6)
• EPA Substance Registry System: Rebeprazole sulfone N-oxide(924663-37-6)

Safety Data

• Hazardous Substances Data: 924663-37-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H21N3O5S/c1-13-16(21(22)9-8-17(13)26-11-5-10-25-2)12-27(23,24)18-19-14-6-3-4-7-15(14)20-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,19,20)

Upstream product

• 117977-21-6 rabeprazole sulfide 
• 924663-40-1 2-[[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole 
• 924663-39-8 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine 1-oxide 
• 103312-62-5 2-[(4-chloro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 
• 152402-97-6 2-chloromethyl-4-chloro-3-methylpyridine hydrochloride 
• 134469-07-1 Benzimidazol-2-thiol 
• 117976-89-3 rabeprazole 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 

Downstream Products

• 117976-47-3 LY 307640 sulfone 

Relevant articles and documents

Rabeprazole correlate D synthetic method

The present invention relates to a rabeprazole correlate D synthesis method, which comprises that: (1) in the presence of an excess oxidizing agent, a thioether compound 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methyl]thio]benzimidazole is oxidized to produce an oxide C; and (2) in the presence of an acid and a reducing agent, the oxide C formed in the step (1) is reduced so as to form the rabeprazole correlate D.

Synthesis of metabolites and related substances of rabeprazole, an anti-ulcerative drug

Rabeprazole sodium (Aciphex) is a gastric proton pump inhibitor used for the prevention and treatment of gastric acid-related diseases. During the synthesis of bulk drug of rabeprazole sodium, we have observed metabolites rabeprazole sulfide and rabeprazole sulfone and related substances rabeprazole-N-oxide, rabeprazole sulfone-N-oxide, N-aralkyl rabeprazole, chloro rabeprazole, and methoxy rabeprazole as impurities in the drug substance. The present work describes the synthesis and characterization of these compounds. Copyright Taylor & Francis Group, LLC.

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.

Synthetic studies connected with the preparation of H+/K +-ATPase inhibitors rabeprazole and lansoprazole

Synthesis of lansoprazole and rabeprazole using common intermediates is devised. The common intermediates, 2-[(4-nitro-3-methylpyridin-2-yl) methanesulfanyl]-1H-benzoimidazole and 2-[(4-chloro-3-methyl-pyridin-2-yl) methanesulfanyl]-1H-benzoimidazole, were prepared in several ways.