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Synthesis method of moxifloxacin hydrochloride intermediate

A technology of moxifloxacin hydrochloride and a synthesis method is applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, organic chemistry, etc., and can solve the problems of many steps, complex synthesis process, complicated operation and the like, To achieve the effect of easy operation and simple synthesis route

Inactive Publication Date: 2014-09-10
CHENGDU CLIMB PHARMA TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinolinyl-3-carboxylic acid-O3,O4-borylacetate is a synthetic hydrochloric acid An important intermediate of moxifloxacin, the molecular formula is as shown in (II), and the synthesis process of this intermediate in the prior art is complicated, the operation is cumbersome, there are many steps, and the yield is low

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  • Synthesis method of moxifloxacin hydrochloride intermediate
  • Synthesis method of moxifloxacin hydrochloride intermediate
  • Synthesis method of moxifloxacin hydrochloride intermediate

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Embodiment 1

[0020] Embodiment 1: a kind of synthetic method of moxifloxacin hydrochloride intermediate, it comprises the following steps:

[0021] S1. Chelation reaction: Add 280g acetic anhydride and 120g glacial acetic acid in turn in the reaction kettle, stir and add 5g anhydrous zinc chloride; heat up, add 80g triethyl borate dropwise when the temperature in the reaction kettle is 40°C, drop Continue to keep stirring at the temperature for 3 hours after the addition is completed, add 150 g gaticycline ester after completion, raise the temperature to 70°C, and track the reaction with TLC until the conversion of gaticyclate is complete;

[0022] S2. Post-processing: After the reaction, the temperature in the kettle was lowered to 15°C, stirred and crystallized for 20 hours, centrifugally filtered, and the obtained crystalline solid was beaten twice with purified water, each time for 20 minutes, and the slurry was filtered, then beaten with ethanol for 20 minutes, and centrifugally filter...

Embodiment 2

[0023] Embodiment 2: a kind of synthetic method of moxifloxacin hydrochloride intermediate, it comprises the following steps:

[0024] S1. Chelation reaction: Add 280g acetic anhydride and 120g glacial acetic acid in turn in the reaction kettle, stir and add 5g anhydrous zinc chloride, heat up, when the temperature in the reaction kettle is 50°C, add 120g triethyl borate dropwise, drop Continue stirring for 5 hours after the addition is complete, add 150 g gaticycline ester after completion, raise the temperature to 75°C, and track the reaction with TLC until the conversion of gaticyclate is complete;

[0025] S2. Post-processing: After the reaction is completed, lower the temperature in the kettle to 25°C and stir for 25 hours to crystallize, then centrifuge and filter the obtained crystalline solid with purified water for 2 times, 30 minutes each time, filter the slurry, and then use ethanol to beat for 30 minutes. After centrifugal filtration, the obtained solid was dried w...

Embodiment 3

[0026] Embodiment 3: a kind of synthetic method of moxifloxacin hydrochloride intermediate, it comprises the following steps:

[0027] S1. Chelation reaction: Add 300g acetic anhydride and 120g glacial acetic acid in turn in the reactor, stir and add 5g anhydrous zinc chloride; heat up, when the temperature in the reactor is 58°C, add 150g triethyl borate dropwise, drop Continue stirring for 3.5 hours after the addition is complete, add 150 g gaticycline ester after completion, raise the temperature to 90°C, track the reaction with TLC until the conversion of gaticyclate is complete;

[0028] S2. Post-processing: After the reaction, the temperature in the kettle was lowered to 18°C, stirred and crystallized for 28 hours, centrifugally filtered, and the obtained crystalline solid was beaten twice with purified water, each time for 23 minutes, and the slurry was filtered, then beaten with ethanol for 25 minutes, and centrifugally filtered again. The obtained solid was dried with...

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Abstract

The invention discloses a synthesis method of a moxifloxacin hydrochloride intermediate, and belongs to the field of medical intermediate synthesis. The synthesis method comprises the following steps: S1, chelation reaction: sequentially adding acetic oxide and glacial acetic acid to a reaction kettle, agitating and adding anhydrous zinc chloride, dropwise adding triethyl borate, carrying out agitated reaction after dropwise adding is ended and then adding a gatifloxacin intermediate, and reacting at 70-100 DEG C until the gatifloxacin intermediate is completely transformed; and S2, post-treatment: cooling and crystallizing a liquid in the reaction kettle, centrifugally filtering, pulping the obtained solid by using purified water and ethanol respectively and then centrifugally filtering again, and preparing the moxifloxacin hydrochloride intermediate after drying the solid. The method disclosed by the invention has the advantages of being easy to operate, simple in synthesis and high in yield. The yield of the product prepared by adopting the method disclosed by the invention is over 85%, the purity can be up to over 99%, and the moisture is smaller than or equal to 2%.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of a moxifloxacin hydrochloride intermediate. Background technique [0002] Moxifloxacin hydrochloride (Moxifloxacinhydrochloride), as shown in formula (I), chemical name is 1-cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonane-8 -yl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinoline carboxylic acid hydrochloride, is the fourth generation of quinolone spectrum antibacterial drugs. Moxifloxacin hydrochloride has shown spectrum antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, anaerobic bacteria, acid-fast bacteria, and atypical microorganisms (such as mycoplasma, chlamydia) in vitro. Moxifloxacin hydrochloride was first launched in Germany in 1999, and in the United States in December of the same year. The dosage forms currently on the market in my country include injections and tablets, which are mainly used to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04
Inventor 曾同建叶丁唐锐郭瑞
Owner CHENGDU CLIMB PHARMA TECH
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