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

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

Uses

Used in Pharmaceutical Industry:
Ufiprazole is used as a metabolite of Omeprazole for its role in the production of gastric proton pump inhibitors, which are essential in treating various gastrointestinal disorders. Its presence as a degradation product also contributes to the overall efficacy and safety profile of the final drug products.
Used in Drug Metabolism Studies:
Ufiprazole is used as a research compound in drug metabolism studies, particularly focusing on its inhibitory effects on cytochrome P450 2C19. This information is crucial for understanding drug interactions and optimizing dosing regimens for patients.

Synthesis

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

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

• 142885-91-4 5-methoxy-2-(((3,5-dimethyl-4-nitro-2-pyridinyl)methyl)thio)-1H-benzimidazole 
• 780752-32-1 4-methoxy-3,5-dimethyl-2-pyridinemethyl bromide 
• 37052-78-1 6-methoxy-1H-benzoimidazole-2-thiol 
• 73590-58-6 omeprazole 
• 60-24-2 2-hydroxyethanethiol 
• 102283-11-4 omeprazole-2-mercaptoethanol disulfide 
• 102283-10-3 2-(2-hydroxyethyldisulfanylmethyl)-4-methoxy-1-(5-methoxybenzimidazol-2-yl)-3,5-dimethylpyridinium 
• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 73590-58-6 omeprazole 
• 37052-78-1 5-methoxy-1,3-dihydro-2H-benzo[d]imidazole-2-thione 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 233610-77-0 2-benzenesulfonyl-4-methoxy-3,5-dimethylpyridine 

Downstream Products

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

Relevant articles and documents

Coupling and optimisation of online nuclear magnetic resonance spectroscopy and mass spectrometry for process monitoring to cover the broad range of process concentration

Real time online monitoring of chemical processes can be carried out by a number of analytical techniques, including optical and vibrational spectroscopies, nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). As each technique has unique advantages and challenges, combinations are an attractive option. The combination of a 500-MHz 1H NMR and a small footprint mass spectrometer to monitor a batch reaction at process concentration was investigated. The mass spectrometer was coupled into the flow path of an online reaction monitoring NMR. Reaction mixture was pumped from a 100-ml vessel to an NMR flow tube before returning to the vessel. Small aliquots were diverted into a sampling make-up flow using an active flow splitter and passed to the mass spectrometer. Advantages of the combination were observed. 1H NMR was ideal for quantitation of high level components, whereas MS showed a greater capability for detecting those at low level. In preliminary experiments MS produced a limited linear relationship with concentration (0.02% to 2% relative concentration, 0.01 mg/ml–1.25 mg/ml), because of signal saturation at the higher concentrations. NMR was unable to detect components below 0.1% relative to concentration maximum. Optimisation of sample transfer to the MS extended the linearity to 10% relative to the concentration maximum. Therefore, the combination of online NMR and MS allows both qualitative and quantitative analysis of reaction components over the full process range. The application of the combination was demonstrated by monitoring a batch chemical reaction and this is described. Copyright

Synthetic method and application of omeprazole

The invention belongs to the field of medicine synthesis, and discloses a synthetic method of omeprazole. The synthetic method comprises the following steps: reacting sodium (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinate to generate (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride, and then carrying out Suzuki reaction on the (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride and (6-methoxy-1H-benzo [d] imidazole-2-yl) boric acid to generate omeprazole. According to the synthetic method of omeprazole, the omeprazole which is easy to purify and stable in yield is obtained by using raw materials which are easy to obtain, and a synthetic method which is simple, easy to operate and control, mild in reaction condition and capable of replacing high-risk reagents such as butyl lithium and the like by using a common reagent. The invention also provides an application of the synthetic method of omeprazole. The synthetic method is suitable for synthesis of omeprazole. The obtained omeprazole is used for preparing an omeprazole injection.

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.

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.

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Preparation method of esomeprazole magnesium trihydrate (by machine translation)

The preparation method of the esomeprazole magnesium trihydrate, comprises the following steps :1): extracting 5 - methoxyl - 2 2-mercaptobenzimidazole and 2 - chloromethyl - 3333,5-dimethyl - 4 4-methoxyl pyridine hydrochloride to form omeprazole sodium salt ;2) by carrying out suction filtration drying, to form omeprazole (omeprazole) chiral compound, and adding an inorganic base organic solution, to an inorganic base organic solution . The preparation method has the advantages of high product, purity ;3) yield, simple, process, high ;4) efficiency, low cost and the like obtained in step, by suction filtration. 3). The preparation method comprises the following steps: dissolving omeprazole sodium salt ;5) with an organic solvent, and carrying out a suction filtration drying step 4); and carrying out suction filtration on omeprazole, and adding an inorganic oxidizing, agent to the inorganic base organic solution, layer, by a suction filtration drying, process ;6) to form the esomeprazole, sodium, salt solution layer by a. centrifugal, drying ;7) preparation method, and a preparation method of the esomeprazole, inorganic salt solution layer are carried out in an unsymmetrical oxidation reaction 6). (by machine translation)

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.

Preparation method of esomeprazole sodium thioether intermediate

The invention relates to a preparation method of an esomeprazole sodium thioether intermediate. Through the adjustment of a process method, the water content of the esomeprazole sodium thioether intermediate 5-methoxy-2[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfanyl]-1H-benzimidazole is controlled below 0.03%, which facilitates more effective control of the water content in a subsequent oxidation reaction system and ensures the high selectivity, high stability, strong controllability and reproducibility of a selective oxidation reaction. The preparation method of the invention has good reproducibility and is more beneficial to large-scale production.

Esomeprazole sodium and lyophilized preparation comprising same

The invention provides esomeprazole sodium and a lyophilized preparation comprising the same. A preparation method of esomeprazole sodium includes following steps: 1), synthesizing an intermediate; 2), synthesizing esomeprazole sodium; 3), roughly preparing esomeprazole sodium; 4), finely preparing esomeprazole sodium. Esomeprazole sodium prepared by the method is higher in preparation accuracy and safer to use; the preparation process is easier to control, and step decomposition brings convenience to quality control of middle steps, so that ensuring of preparation accuracy of esomeprazole sodium is facilitated, and drug prepared from esomeprazole sodium is safer.

Method for preparing high-purity esomeprazole magnesium

The invention relates to a method for preparing high-purity esomeprazole magnesium. The method comprises the following steps: mixing omeprazole sulfide, diethyl tartrate and titanium isopropoxide, adding diisopropylethylamine, performing stirring, dropping cumene hydroperoxide, and performing separation so as to obtain an oil substance; adding a strong base, performing stirring, adding the strongbase time by time, performing extraction and washing, performing TLC (thin-layer chromatography) monitoring, and stopping adding the strong base when trace points are generally vanished; performing cooling, crystal separation, filtration and leaching so as to obtain an esomeprazole salt; dissolving the esomeprazole salt with water, reducing the temperature to 20 DEG C or less, adjusting the pH value, dropping a magnesium sulfate heptahydrate solution, and after dropping, performing stirring, filtration, leaching and drying so as to obtain a crude product of esomeprazole; dissolving the crude product of the esomeprazole with methanol, performing decoloring with activated carbon, performing filtration, concentration and secondary dissolution, adding an acetone solution, and performing stirring, suction filtration and drying, so as to obtain the esomeprazole magnesium. The product prepared by using the method is high in purity, high in yield and small in impurity.