- Site selective syntheses of [3H]omeprazole using hydrogen isotope exchange chemistry
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Omeprazole (Prilosec) is a selective and irreversible proton pump inhibitor used to treat various medical conditions related to the production of excess stomach acids. It functions by suppressing secretion of those acids. Radiolabeled compounds are commonly employed in the drug discovery and development process to support efforts including library screening, target identification, receptor binding, assay development and validation and safety assessment. Herein, we describe synthetic approaches to the controlled and selective labeling of omeprazole with tritium via hydrogen isotope exchange chemistry. The chemistry may also be used to prepare tritium labeled esomeprazole (Nexium), the active pure (S)-enantiomer of omeprazole.
- Pollack, Scott R.,Schenk, David J.
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- Preparation method of omeprazole midbody
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The invention relates to a preparation method of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine shown in a chemical structural formula I. The method is characterized by comprising the steps of a catalytic hydrogenation reaction, wherein Raney nickel or Pd/C is selected as a catalyst; a chlorination reaction, wherein YCln is selected from N-chloroacetamides or N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin or dichlord isocyanurice acid or symclosene; n is selected from 3 or 2 or 1; m is selected from 0 or 1 or 2.
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Paragraph 0053-0064
(2019/10/22)
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- Preparation method of 4-methoxy-2,3,5-trimethylpyridine
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The invention belongs to the field of chemical intermediate preparation and specifically relates to a preparation method of 4-methoxy-2,3,5-trimethylpyridine. The preparation method comprises the following steps: 4-methoxy-2,3,5-trimethylpyridine-N-oxide is firstly obtained, and then 4-methoxy-2,3,5-trimethylpyridine is obtained. The preparation method has the characteristics of high yield, cheapraw material, simple process and good product quality. Thus, the preparation method has a certain application value.
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Paragraph 0011; 0012; 0013; 0014
(2019/07/11)
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With the aid of DCx and DPP Omeprazol (1) can be determined in Britton-Robinson-buffers (BRP, pH 7-9) up to a concentration of 10~5 M. The mechanism of the reduction process on the DME could be elucidated. With consumption of two electrons and two protons 1 will be reduced to 5-methoxy-2-[(3,5-dimethyl-4-methoxypyridin-2-yl)methylthio]-l Hbenzimidazole which will be cleaved with uptake of two further electrons and two protons into 4-methoxy-2,3,5-trimethylpyridine and 2-mercapto-5-methoxybenzimidazole.
- Knoth,Oelschlaeger,Volke,Ludvik
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p. 686 - 691
(2007/10/03)
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- Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.
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A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.
- Mittelbach,Schmidt,Uray,Junek,Lamm,Ankner,Br?ndstr?m,Simonsson
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p. 524 - 529
(2007/10/02)
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- 2,4-dichloro-3,5,6-trimethylpyridine
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A method for the preparation of 2,3,5-trimethylpyridine and some of its derivatives.
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