Pharmaceutical intermediate 2,6-dicarboxylic acid pyridine synthesis method

A technology of pyridine dicarboxylate and a synthesis method, which is applied in the field of synthesis of a pharmaceutical intermediate 2,6-pyridine dicarboxylate, can solve the problems of low yield and complicated process, and achieves shortening reaction time, reducing intermediate links, improving The effect of reaction yield

Inactive Publication Date: 2018-07-03
CHENGDU DONG DIAN AI ER TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Pyridine 2,6-dicarboxylate is mainly used as a competitive inhibitor of bovine liver glutamate dehydrogenase, and can also be used to prepare ligand complexes of lanthanum and transition metals. However, most of the existing synthetic methods use 2,6 -Lutidine is used as a reactant, the process is more complicated, and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method, which is important for further improving the quality and yield of the product and reducing the content of by-products economic significance

Method used

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  • Pharmaceutical intermediate 2,6-dicarboxylic acid pyridine synthesis method

Examples

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Effect test

example 1

[0010] Add 2mol of 2-isopropyl-3,5-dihydroxy-6-ethylpyridine and 5mol mass fraction of 70% ethylene glycol monomethyl ether solution in the reaction vessel, control the stirring speed to 190rpm, and raise the solution temperature To 60 ° C, add 3 mol of bismuth trichloride, keep for 40 min, lower the solution temperature to 5 ° C, precipitate precipitate, filter, wash with 30% potassium nitrate solution for 3 times, combine the filtrate and washing liquid, control the stirring speed 110rpm, adjust the pH to 2 by a 20% oxalic acid solution in mass fraction, wash with a 70% N-benzylmethylamine solution, and wash with an 80% benzyl methyl ether solution in a mass fraction of Recrystallized in 92% propyl phenyl ketone solution, and crystals were precipitated to obtain 303.94 g of finished product pyridine 2,6-dicarboxylate, with a yield of 91%.

example 2

[0012] Add 2mol of 2-isopropyl-3,5-dihydroxy-6-ethylpyridine and 6mol mass fraction of 75% ethylene glycol monomethyl ether solution in the reaction vessel, control the stirring speed to 210rpm, and increase the solution temperature To 63 ° C, add 3.5 mol of bismuth trichloride, keep for 50 min, lower the solution temperature to 7 ° C, precipitate out, filter, wash with 35% potassium nitrate solution for 5 times, combine the filtrate and washing liquid, and control the stirring speed 120rpm, adjust the pH to 2.5 by mass fraction of 25% oxalic acid solution, wash with mass fraction of 73% N-benzylmethylamine solution, mass fraction of 83% benzyl methyl ether solution wash, at mass fraction of 94 % propyl phenyl ketone solution to recrystallize and precipitate crystals to obtain 310.62 g of finished product pyridine 2,6-dicarboxylate with a yield of 93%.

example 3

[0014] Add 2mol of 2-isopropyl-3,5-dihydroxy-6-ethylpyridine and 7mol mass fraction of 80% ethylene glycol monomethyl ether solution in the reaction vessel, control the stirring speed to 230rpm, and raise the solution temperature To 67 ° C, add 4 mol of bismuth trichloride, keep for 60 min, lower the solution temperature to 9 ° C, precipitate out, filter, wash 7 times with potassium nitrate solution with a mass fraction of 40%, combine the filtrate and washing liquid, and control the stirring speed 130rpm, adjust the pH to 3 by a 28% oxalic acid solution, wash with a 78% N-benzylmethylamine solution, and wash with an 86% benzyl methyl ether solution. Recrystallized in 97% propyl phenyl ketone solution, and crystals were precipitated to obtain 320.64 g of finished product pyridine 2,6-dicarboxylate, with a yield of 96%.

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Abstract

The invention relates to a pharmaceutical intermediate 2,6-dicarboxylic acid pyridine synthesis method, which mainly comprises: adding 2 mol 2-isopropyl-3,5-dihydroxy-6-ethyl pyridine and 5-7 mol ethylene glycol-methyl ether solution into a reaction container, controlling the stirring speed at 190-230 rpm, increasing the temperature of the solution to 60-67 DEG C, adding 3-4 mol antimony trichloride, maintaining for 40-60 min, reducing the solution temperature to 5-9 DEG C, precipitating the precipitate, filtering, washing 3-7 times with a potassium nitrate solution, combining the filtrate andthe washing solution, controlling the stirring speed at 110-130 rpm, adjusting the pH value to 2-3 with an oxalic acid solution, washing with a N-benzylmethylamine solution, washing with a benzyl methyl ether solution, re-crystallizing in a propyl phenyl ketone solution, and precipitating the crystal to obtain the finished product 2,6-dicarboxylic acid pyridine.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, pyridine 2,6-dicarboxylate. Background technique [0002] Pyridine 2,6-dicarboxylate is mainly used as a competitive inhibitor of bovine liver glutamate dehydrogenase, and can also be used to prepare ligand complexes of lanthanum and transition metals. However, most of the existing synthetic methods use 2,6 -Lutidine is used as a reactant, the process is more complicated, and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method, which is important for further improving the quality and yield of the product and reducing the content of by-products economic significance. Contents of the invention [0003] The object of the present invention is to provide a kind of synthetic method of pharmaceutical intermediate 2,6-dicarboxylic acid pyridine, comprising the following steps: [0004] (i) Add 2mol of 2-isopropyl-3,5-dihydroxy-6-ethy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/79C07D213/803
CPCC07D213/79C07D213/803
Inventor 严义达
Owner CHENGDU DONG DIAN AI ER TECH
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