73590-85-9

Basic information

• Product Name: Ufiprazole
• Synonyms: H 168/22;5-METHOXY-2-(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL THIO-1H-BENZIMIDAZOLE;5-METHOXY-2-(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYLMERCAPTOBENZIMIDAZOLE;5-METHOXY-2-[[(3,5-DIMETHYL-4-METHOXY PYRIDINYL)-METHYL]THIO]-1H-BENZIMIDAZOLE;2-[(4-METHOXYETHOXY-3,5-DIMETHYL-2-PYRIDINYL)-METHYLTHIO]-5-METHOXYBENZIMIDAZOLE;2-{[(3,5-dimethyl-4-methoxy-2-pyridinyl)-methyl]-thio}-5-methoxy-1h-benzimidazole;OMEPRAZOLE SULPHIDE;ufiprazole
• CAS NO: 73590-85-9
• Molecular Formula: C₁₇H₁₉N₃O₂S
• Molecular Weight: 329.42
• EINECS: 208-591-9
• Product Categories: (intermediate of lamivudine);Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;zjh;Inhibitors
• Mol File: 73590-85-9.mol
• Article Data: 48

Chemical Properties

• Melting Point: 122.0 to 126.0 °C
• Boiling Point: 539.7 °C at 760 mmHg
• Flash Point: 280.2 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 1.03E-11mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.81±0.10(Predicted)
• CAS DataBase Reference: Ufiprazole(CAS DataBase Reference)
• NIST Chemistry Reference: Ufiprazole(73590-85-9)
• EPA Substance Registry System: Ufiprazole(73590-85-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 73590-85-9(Hazardous Substances Data)

Usage

Synthesis

Ufiprazole can be synthesized by the condensation reaction of 2-mercapto-5-methoxybenzimidazole and 2-chloromethyl-4-methoxy-3,5-lutidine.

Description

Omeprazole sulfide is an intermediate used in the production of the gastric proton pump inhibitors, omeprazole and esomeprazole . As a degradation product, it is reported to be a direct-acting inhibitor of cytochrome P450 2C19 in pooled human liver microsomes (IC50 = 9.7 μM).

Uses

Different sources of media describe the Uses of 73590-85-9 differently. You can refer to the following data:
1. A metabolite of Omeprazole
2. Omeprazole Sulfide (Esomeprazol EP Impurity C(Omeprazole EP Impurity C)) is a metabolite of Omeprazole.

Biological Activity

Ufiprazole (Omeprazole sulfide) is an intermediate in the production of gastric proton pump inhibitors omeprazole and esomeprazole.

InChI:InChI=1/C17H19N3O2S/c1-10-8-18-15(11(2)16(10)22-4)9-23-17-19-13-6-5-12(21-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

Upstream product

• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 37052-78-1 5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione 
• 73590-58-6 omeprazole 
• 73590-58-6 omeprazole 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 233610-77-0 2-benzenesulfonyl-4-methoxy-3,5-dimethylpyridine 
• 91168-31-9 2-methylthio-5-methoxy-1H-benzimidazole 
• 142885-91-4 5-methoxy-2-(((3,5-dimethyl-4-nitro-2-pyridinyl)methyl)thio)-1H-benzimidazole 
• 124-41-4 sodium methylate 
• 220757-74-4 5-methoxy-2-{[(4-chloro-3,5-dimethyl-pyridin-2-yl)methyl]thio}-1H-benzimidazole 
• 84006-10-0 (chloromethyl)-4-methoxy-3,5-dimethylpyridine 
• 37052-78-1 6-methoxy-1H-benzoimidazole-2-thiol 

Downstream Products

• 73590-58-6 omeprazole 
• 119141-89-8 (R)-omeprazole 
• 119141-88-7 esomeprazole 
• 73590-58-6 omeprazole 
• 119141-88-7 (S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole 
• 119141-89-8 (R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole 
• 103876-98-8 2-{[(6-methoxy-1H-benzimidazol-2-yl)thio]methyl}-3,5-dimethyl-4-pyridinol 
• 88546-55-8 omeprazole sulfone 
• 161973-11-1 esomeprazole magnesium 
• 149-57-5 2-Ethylhexanoic acid 

Relevant articles and documents

The Mechanism of Action of the Gastric Acid Secretion Inhibitor Omeprazole

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Synthetic method of esomeprazole

The invention discloses a synthetic method of esomeprazole, which comprises the following steps: first steps of preparation of omeprazole thioether. 2nd: The crude product is prepared by taking omeprazole thioether and the like as a raw material. The obtained crude product was subjected to a purification operation 3 times to give a refined intermediate. The third Steps. The purified intermediate is mixed with deionized water, filtered, mixed with magnesium chloride hexahydrate and deionized water, stirred, cooled, stirred 30 min, decompressed and suction filtered, and the obtained crystals are washed with distilled water and dried to obtain esomeprazole. Under the condition of ensuring 90%, the yield and purity of the subsequent processing process are improved, and the problems that in the prior art, the purity is not ideal, the total yield is low, the production cost is increased, and the industrial production is not conducive to industrial production are solved.

Synthesis method of esomeprazole sodium

The invention discloses a synthesis method of esomeprazole sodium. Belong to organic synthesis field. Of 5 - methoxy -2-mercaptobenzimidazole in ethanol - sodium hydroxide solution react with 2 - chloromethyl -3 and 5 -dimethyl -4 - methoxypyridine hydrochloride to obtain omeprazole thioether. The synthetic method is high in raw material utilization rate, reduces the content and kinds of impurities, greatly improves the extraction rate of esomeprazole sodium, can reach 75%, and has a purity of more than 99%. The synthetic route is short, and the synthesis cost is greatly reduced.

Preparation method of esomeprazole sodium

The invention provides a preparation method of esomeprazole sodium, specifically a preparation method of optically pure esomeprazole sodium. The preparation method comprises the step of preparing esomeprazole sodium by taking 2-mercapto-5-methoxy-1H-benzimidazole and 2-chloromethyl-4-methoxy-3,5-dimethyl pyridine hydrochloride as starting raw materials. The method provided by the invention has good selectivity, can obtain almost optically pure products, and is suitable for industrial production of esomeprazole sodium.