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Gatifloxacin and its synthetic method

A technology of gatifloxacin and synthetic methods, applied in the direction of organic chemistry, etc., can solve problems such as time-consuming

Active Publication Date: 2021-06-01
HUAIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Based on this, it is necessary to provide a kind of gatifloxacin and its synthetic method for the problem that the synthetic method of traditional gatifloxacin takes a long time

Method used

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  • Gatifloxacin and its synthetic method
  • Gatifloxacin and its synthetic method

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preparation example Construction

[0029] The present invention provides a synthetic method of gatifloxacin in one embodiment, comprising the steps of:

[0030] S1. Mix N,N-ethyl dimethylaminoacrylate, 2,4,5-trifluoro-3-methoxybenzoyl chloride, ethyl acetate and triethylamine, and obtain the first intermediate after the reaction is complete ; The structural formula of the first intermediate is as follows:

[0031]

[0032] The reaction principle of step S1 is that under the action of triethylamine, ethyl N,N-dimethylaminoacrylate is coupled with 2,4,5-trifluoro-3-methoxybenzoyl chloride in ethyl acetate The reaction affords the first intermediate.

[0033] In one embodiment, the ratio of N,N-ethyl dimethylaminoacrylate to 2,4,5-trifluoro-3-methoxybenzoyl chloride is (0.9˜1.1):1. The volume ratio of ethyl acetate to 2,4,5-trifluoro-3-methoxybenzoyl chloride is (10-20):1.

[0034] Further, the conditions for mixing and reacting N,N-ethyl dimethylaminoacrylate, 2,4,5-trifluoro-3-methoxybenzoyl chloride, ethy...

Embodiment 1

[0062] Put 15.0g of ethyl N,N-dimethylaminoacrylate into the reaction flask, then put in 11.11g of triethylamine and 100ml of ethyl acetate, stir and mix and heat to 60°C to get 2,4,5-trifluoro - 22.5g of 3-methoxybenzoyl chloride, dissolved in 100ml of ethyl acetate, then slowly drop the dissolved substance into the reaction flask, after 1 hour, the temperature was increased to 80°C, and the reaction was stirred for 2h. After cooling to room temperature, add 6.6 g of acetic acid for acidification, drop in 5.7 g of cyclopropylamine and continue stirring for 0.5 hour, add 120 ml of distilled water, transfer the mixed liquid to a separatory funnel, remove the upper water layer, and wash once with distilled water. Extract the aqueous layer with 100ml of ethyl acetate, combine the organic layers into the reaction flask, add 27.6g of potassium hydroxide, adjust the temperature to 140°C to remove water, cool after 7 hours, and distill the ethyl acetate under reduced pressure A brown...

Embodiment 2

[0066] Put 15.0g of ethyl N,N-dimethylaminoacrylate into the reaction flask, then put in 11.11g of triethylamine and 100ml of ethyl acetate, stir and mix and heat to 60°C to get 2,4,5-trifluoro - 22.5g of 3-methoxybenzoyl chloride, dissolved in 100ml of ethyl acetate, then slowly drop the dissolved substance into the reaction flask, after 1 hour, the temperature was increased to 80°C, and the reaction was stirred for 1h, After cooling to room temperature, add 6.6 g of acetic acid for acidification, drop in 5.7 g of cyclopropylamine and continue stirring for 0.5 hour, add 120 ml of distilled water, transfer the mixed liquid to a separatory funnel, remove the upper water layer, and wash once with distilled water. Extract the aqueous layer with 100ml of ethyl acetate, combine the organic layers into the reaction flask, add 27.6g of potassium hydroxide, adjust the temperature to 140°C to remove water, cool after 7 hours, and distill the ethyl acetate under reduced pressure A brown...

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Abstract

The invention relates to a gatifloxacin and a synthesis method thereof. The synthesis method comprises the following steps: mixing N,N-ethyl dimethylaminoacrylate, 2,4,5-trifluoro-3-methoxybenzoyl chloride, ethyl acetate and triethylamine, after the reaction is complete The first intermediate is obtained; the first intermediate is mixed with acetic acid and cyclopropylamine, and the second intermediate is obtained after the reaction is complete; the second intermediate is mixed with a strong base, and the gatifloxacin cyclization ester is obtained after the reaction is complete ; Gatifloxacin cyclic ester is obtained through transesterification reaction to obtain the third intermediate; the third intermediate is mixed with 2-methylpiperazine, and after the reaction is complete, it is hydrolyzed and acidified to obtain Gatifloxacin; wherein, strong base At least one selected from sodium hydroxide and potassium hydroxide. In the synthesis method of gatifloxacin mentioned above, sodium hydroxide and potassium hydroxide are used for ring-forming reaction, so that the time of ring-forming reaction is greatly shortened, and the time cost of synthesizing gatifloxacin is reduced.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to gatifloxacin and a synthesis method thereof. Background technique [0002] The chemical composition of gatifloxacin is 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxo Quinolinyl-3-carboxylic acid, which exists in the form of hydrochloride of the above components, is a synthetic drug and belongs to the fourth-generation quinolone antibacterial drugs containing methoxy groups. Because of its good pharmacokinetics, wide antibacterial spectrum, strong antibacterial activity against Gram-positive bacteria and anaerobic bacteria, fast absorption, wide distribution in various tissues of the body, stable drug efficacy, and low toxicity And adverse reactions are small, especially the central nervous system and phototoxicity are small, the safety is high, and the patient's tolerance is good, so it is widely used in clinical practice. In the traditiona...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D215/56
CPCC07D215/56C07D401/04
Inventor 罗琼林苏胜培舒友李勇欧阳跃军胡扬剑李元祥
Owner HUAIHUA UNIV
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