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Purification method of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl) pyridine

A purification method and tetrazole technology are applied in the field of purification of 5-bromo-2-pyridine, which can solve the problems of low product purity and achieve the effects of high purity, high yield, broad development and application prospects

Pending Publication Date: 2020-06-16
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The object of the present invention is to provide a purification method of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, which has mild purification conditions, safety, easy operation, high purity and high yield High-level features, while reducing production costs, overcoming the problems of using a large amount of isopropyl acetate in the existing process, low product purity, and requiring multiple recrystallizations

Method used

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  • Purification method of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl) pyridine

Examples

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Embodiment 1

[0036] 1) Put 200g of dichloromethane into the reaction vessel, add 50g (0.2mol) of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, and add 20% hydrogen chloride dropwise under stirring. 38g (0.21mol) ethanol solution, kept for 3 hours; cooled to 10℃, filtered, washed with 20g ethanol, and dried to obtain 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine hydrochloric acid 56g of salt;

[0037] 2) Put 260g of pure water into the reaction vessel, add 56g of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine hydrochloride, stir to dissolve, add 100g of dichloromethane, and stir. Add 30g of 30% sodium hydroxide solution dropwise and keep it for 3 hours; cool to 10°C, filter, wash with 50g ethanol, and dry to obtain 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 48g, yield: 96%; liquid chromatographic purity 99.96%, the HPLC chart of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine obtained in Example 1 is as follows figure 1 Shown.

Embodiment 2

[0039] 1) Put 400g of dichloromethane into the reaction vessel, add 50g (0.2mol) of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, and add 20% hydrogen chloride dropwise under stirring. 38g (0.21mol) ethanol solution, kept for 3 hours; cooled to 10℃, filtered, washed with 20g ethanol, and dried to obtain 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine hydrochloric acid 55g of salt;

[0040] 2) Put 500g of pure water into the reaction vessel, add 55g of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine hydrochloride, stir to dissolve, add 300g of dichloromethane, and stir. Drop 31g of 30% sodium hydroxide solution and keep it for 5 hours; cool to 5°C, filter, wash with 100g ethanol, and dry to obtain 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 47.5g, yield: 95%; liquid chromatography purity 99.98%.

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Abstract

The invention discloses a purification method of 5-bromine-2-(2-methyl-2H-tetrazol-5-yl) pyridine. The purification method comprises the following steps: (1) dissolving 5-bromo-2-(2-methyl-2H-tetrazol-5-yl) pyridine in a solvent, dropwise adding an acidic ethanol solution, stirring and heating, keeping, then cooling to separate out crystals, filtering, washing the crystals with ethanol, and dryingto obtain 5-bromo-2-(2-methyl-2H-tetrazol-5-yl) pyridine acid salt; and 2) adding the 5-bromine-2-(2-methyl-2H-tetrazol-5-yl) pyridine salt into water for dissolving, adding a solvent, dropwise adding liquid caustic soda, stirring, heating, keeping, cooling to separate out crystals, filtering, washing the crystals with ethanol, and drying to obtain the 5-bromine-2-(2-methyl-2H-tetrazol-5-yl) pyridine. The purification method disclosed by the invention has the characteristics of mild purification conditions, safety, simplicity and convenience in operation, high purity, high yield and the like,reduces the production cost, and overcomes the problems of low product purity and need of repeated recrystallization due to the use of a large amount of isopropyl acetate in the existing process.

Description

Technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a purification method of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine. Background technique [0002] 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, molecular formula: C7H6BrN5, CAS number: 380380-64-3. [0003] 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine is a key intermediate for the synthesis of Tedizolidphosphate, developed by CUBIST PHARMS, and belongs to the second generation of oxazolidone Class new anti-bacterial infection drugs. Tedizolamide phosphate is a prodrug of Tedizolamide. After oral or intravenous administration, it is converted into Tedizolamide by phosphatase. Tedizolamide is a second-generation oxazolidinone antibiotic. It is a protein synthesis inhibitor. By binding to the 50S subunit of the bacterial ribosome, it inhibits the synthesis of bacterial protein and exerts antibacterial effects. It is not easy to interact with other types of antibiotics. Prod...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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