102625-64-9Relevant articles and documents
An improved and single-pot process for the production of pantoprazole substantially free from sulfone impurity
Mathad, Vijayavitthal T.,Govindan, Shanmugam,Kolla, Naveen Kumar,Maddipatla, Madhavi,Sajja, Eswaraiah,Sundaram, Venkataraman
, p. 266 - 270 (2004)
Pantoprazole (1), a substituted benzimidazole derivative, is an irreversible proton pump inhibitor, essentially used for the prevention and treatment of gastric acid-related diseases. The process for its preparation generally suffers from the drawback of producing a potential sulfone impurity (5). The present work details a report of the journey towards the development of a simple, single-pot process for the production of pantoprazole, substantially free from sulfone impurity (5). The detailed study of the different parameters affecting the purity and yield of the compound has been presented.
An electronic circular dichroism study for the structurechiroptical relationship of chiral proton pump inhibitors
Zhou, Zhixu,Li, Linwei,Yan, Ning,Du, Lei,Sun, Changshan,Sun, Tiemin
, p. 110 - 112 (2016)
In this paper, we investigated the electronic circular dichroism (ECD) of proton pump inhibitors (PPIs) using a method of combining experimental spectrum and time-dependent density functional theory (TD-DFT) calculations. In our research, an intriguing helicity-like phenomenon was discovered for the relationship between static dipole moment and ECD curves of different conformers in lansoprazole. The scope and validity of the precious phenomenon have been examined by four PPIs using the same method. Hence, it can be used as a reference to determine and verify the absolute configuration of PPIs-type and PPIs-like chiral sulfoxide.
Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
, p. 4161 - 4167 (2018/09/21)
In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
A method for preparing divides the request to pull zuozuo the sodium nitrogen oxide impurity
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Paragraph 0012; 0027; 0028, (2017/10/05)
The present invention discloses a preparation method for a pantoprazole sodium oxynitride impurity. The preparation method comprises the following steps: 2-chloromethyl-3,4-dimethoxypyridine hydrochloride is used as a raw material to react with 5-difluoromethoxy-2-mercapto-1H-benzimidazole and produce 5-difluoromethoxy-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulphur}-1H-benzimidazole; then in a presence of hydrogen peroxide and acetic acid, with copper hydroxyphosphate as a catalyst, oxidation is performed to obtain an oxynitride product of the pantoprazole; and finally a sodium salt is obtained by a reaction with sodium hydroxide, and pantoprazole sodium oxynitride impurity is obtained. According to the preparation method, no extreme reaction condition is needed, and raw materials are easy to obtain; the oxidant is capable of selective oxidations, which can not only oxidate pyridine ring, but also can oxidate thioether to sulfoxide, and by controlling the dosage of the catalyst, i.e., copper hydroxyphosphate, a peroxidation is less likely to occur (oxidate thioether to sulphone); and a post-treatment is simple and easy in operation, and the resulting product is high in purity and high in yield.