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Intermediate compound for chemical synthesis preparation of sanguinarine and preparation method thereof

A chemical synthesis and compound technology, applied in the direction of organic chemistry, can solve the problems of high irritation of intermediates, ineffective treatment of waste water, long reaction steps, etc., and achieve the effects of short synthesis route, improved labor safety and low production cost

Active Publication Date: 2022-05-10
NINGBO CHEMGOO PHAMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] (3) The chemical synthesis method of existing report needs to use iodide or bromide intermediate coupling reaction to prepare benzo [c] phenanthridine skeleton, and iodide or bromide raw material and intermediate are irritating greatly, need self-preparation, reaction The steps are long, and a large amount of waste water containing iodine or bromine cannot be effectively treated

Method used

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  • Intermediate compound for chemical synthesis preparation of sanguinarine and preparation method thereof
  • Intermediate compound for chemical synthesis preparation of sanguinarine and preparation method thereof
  • Intermediate compound for chemical synthesis preparation of sanguinarine and preparation method thereof

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preparation example Construction

[0042] The preparation method and synthesis route of the above intermediate compounds are as follows:

[0043]

[0044] Compound C is prepared from compound A and compound B by condensation reaction, which is the intermediate compound.

[0045] Preferably, the above preparation method specifically includes: compound a reacts with dichlorosulfoxide first, and then prepares compound C through condensation reaction with compound B; The condensation reaction is carried out under alkaline conditions.

[0046] Preferably, the alkaline condition is provided by an organic base or an inorganic base. Further, the organic base is selected from triethylamine, diisopropylamine, diisopropylethylamine, etc; The inorganic base is selected from sodium carbonate, sodium bicarbonate, sodium hydroxide, etc., the reaction solvent of the condensation reaction is selected from dichloromethane, ethyl acetate, toluene, chlorobenzene, etc., and the reaction temperature is - 10 ~ 110 ℃, preferably 0-40 ℃....

Embodiment 1

[0058] Example 1: preparation of compound I

[0059]

[0060] Add compound a (5g, 30mmol) and 20ml dichloromethane into reactor 1, add dichlorosulfoxide (3.94g, 33mmol) dropwise, increase temperature and reflux reaction, track TLC to no raw material residue, concentrate under reduced pressure to remove excess dichlorosulfoxide, and dilute with 40ml dichloromethane; Compound B (5.62g, 30mmol), 100ml dichloromethane and triethylamine (3.19g, 31.5mmol) were added into reactor 2. The reaction liquid in reactor 1 was added dropwise to reactor 2 at 0 ℃ and naturally rose to room temperature for reaction. TLC tracked that there was no raw material left, and 5% NaOH and 5% h were used successively 2 SO 4 , washed with saturated salt water, anhydrous Na 2 SO 4 After drying, dichloromethane was recrystallized to obtain 6G white solid, namely compound C, with a yield of 59.5% and a HPLC purity of 98.5%.

[0061] Compound C (5, 14.91mmol), 20mldmf, 60% sodium hydrogen (0.626g, 15.65mmol), M...

Embodiment 2

[0062] Example 2: preparation of compound I

[0063]

[0064] Add compound a (10g, 60mmol) and 40ml toluene into reactor 1, add dichlorosulfoxide (3.94g, 33mmol) dropwise, raise the temperature for 70 ℃ reaction, track TLC to no raw material residue, concentrate under reduced pressure to remove excess dichlorosulfoxide, and dilute 80ml toluene; Compound B (11.2g, 60mmol), 200ml toluene and diisopropyl ethylamine (8.14g, 63mmol) were added into reactor 2. The reaction solution in reactor 1 was added dropwise to reactor 2 at 0 ℃ and naturally rose to room temperature for reaction. TLC tracked that there was no raw material left, and 5% NaOH and 5% h were used successively 2 SO 4 , washed with saturated salt water, anhydrous Na 2 SO 4 After drying, dichloromethane was recrystallized to obtain 13g white solid, namely compound C, with a yield of 64.4% and a HPLC purity of 99.1%.

[0065] Compound C (10g, 29.8mmol), 40mlnmp, 60% sodium hydrogen (1.3g, 32.8mmol) were added to reactor 3. ...

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Abstract

The invention relates to the field of medicine synthesis, and discloses an intermediate compound for chemical synthesis preparation of sanguinarine and a preparation method thereof, the intermediate compound provided by the invention is used for chemical synthesis of sanguinarine, and has the advantages of short steps, mild reaction conditions, low production cost, environmental protection, high yield and high purity. And the high-quality requirements of medicinal products can be met.

Description

technical field [0001] The invention relates to the field of pharmaceutical synthesis, in particular to an intermediate compound for chemical synthesis to prepare sanguinarine and a preparation method thereof. Background technology [0002] Aromatic benzo [C] phenanthridine alkaloids include sanguinarine (SA), chelerythrine (CHE), etc. The main effective chemical components in Macleaya chinensis are sanguinarine and chelerythrine, and the content in fruit is the highest. The extract of bolaihui is obtained from the fruit cheek of bolaihui after extraction and purification. As a feed additive, it can replace antibiotics. [0003] [0004] Methods 1. Resin separation and purification of Macleaya extract. Chen Bo et al. Disclosed the separation and preparation process of high-purity sanguinarine and chelerythrine in the 2004 patent cn1532197: the method takes the extract of Macleaya chinensis or other plant extracts containing sanguinarine and other alkaloids as raw materials, dis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/70C07D491/153
CPCC07D317/70C07D491/153Y02P20/55
Inventor 徐林峰楼科侠张达
Owner NINGBO CHEMGOO PHAMA TECH CO LTD
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