A kind of preparation method of pyrrole compound

A compound and mixture technology, applied in the field of preparation of pyrrole compounds, can solve problems such as difficult industrial production and inconvenient implementation

Active Publication Date: 2020-08-07
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This conventional method needs to prepare the alcoholic solution of hydrogen chloride or needs to use hydrogen chloride gas, is inconvenient to carry out industrially, is difficult to be used in industrial production

Method used

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  • A kind of preparation method of pyrrole compound
  • A kind of preparation method of pyrrole compound
  • A kind of preparation method of pyrrole compound

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preparation example Construction

[0007] The invention provides a method for preparing pyrrole compounds, the reaction conditions of which are simple and easy to operate and control, and are suitable for industrial production. In the method provided by the present invention, a preparation method of pyrrole compound (02), comprising: reacting compound (01) with a halogenating reagent in an organic solvent to obtain compound (02),

[0008]

[0009] Among them, R is C1-C10 (1 carbon to 10 carbons) straight chain or branched chain alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, such as methyl, ethyl, isopropyl base, n-butyl, isobutyl, cyclopropyl, pyridyl, phenyl, etc., R is optionally substituted by halogen, and the halogen is fluorine, chlorine, bromine or iodine; X is chlorine or bromine.

[0010] In some embodiments, R is phenyl. In some embodiments, R is ethyl. In some embodiments, R is 2-fluorophenyl.

[0011] In some embodiments, X is chlorine. In some embodiments, X is bromine.

[0012] The ...

specific Embodiment approach

[0038] In order to enable those skilled in the art to better understand the technical solutions of the present invention, some non-limiting examples are further disclosed below to further describe the present invention in detail.

[0039] The reagents used in the present invention can be purchased from the market or can be prepared by the methods described in the present invention.

[0040] In the present invention, g means gram, mL means milliliter, mol / L means mole / liter, and h means hour.

[0041] In the following examples, the compound shown in the formula (01) shown in the following reaction formula is compound (01), and the compound shown in formula (02) is compound (02):

[0042]

[0043] When R in the present invention is other groups, please refer to the methods in the following examples to prepare other compounds.

[0044] In the present invention, the completion of the reaction means that the remaining amount of the raw material compound (01) is not higher than 5%...

Embodiment 1

[0047] Add 6.17 g of compound (01) to the reaction flask at room temperature, then add 30 mL of homemade 4.07 mol / L ethyl acetate hydrochloride solution, control the temperature at 35°C-45°C, react for 2 hours, and the reaction is complete; the reaction solution is concentrated under reduced pressure to Dry, mix the residue with 24.68mL of ethyl acetate, heat to reflux, and keep at reflux for 1h; then lower the temperature to 45°C and keep warm for 0.5h, then lower the temperature to 30°C and keep warm for 0.5h, then cool down to 0°C and keep warm for 0.5h; After filtration, the obtained solid was dried under reduced pressure at 60° C. to obtain compound (02): 4.80 g of solid with a purity of 96.5% and a yield of 71%. After comparing and analyzing the test results before the post-treatment of the reaction solution and the test results of the product, it was found that an unknown impurity (impurity 1) with a higher content was generated during the reaction process, with a conten...

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Abstract

The invention provides a preparation method of a pyrrole compound and belongs to the technical field of pharmacy. The preparation method comprises that a raw material compound and a halogenation reagent undergo a reaction in an organic solvent to produce a target compound. The halogenation reagent is trimethylchlorosilane, trimethylbromosilane, triethylchlorosilane, tert-butyl dimethylchlorosilane, phenyl dimethylchlorosilane, oxalyl chloride, acetyl chloride, phosphorus oxychloride, phosphorus pentachloride, phosphorus pentabromide, thionyl chloride, sulfuryl chloride or their composition. The preparation method can prevent harsh conditions such as use of hydrogen chloride gas, is carried out under simple reaction conditions, is easy to operate and control and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of pyrrole compound, which belongs to the technical field of pharmacy. Background technique [0002] Pyrrole compounds are intermediate raw materials in the preparation of various medicines, and are widely used in the preparation of medicines. Such as Vonoprazan (English name Vonoprazan, shown in formula (V)), is a kind of antigastric drug, needs to obtain pyrrole compound earlier in its preparation process, and common method is to use cyano compound as raw material, in hydrochloric acid Under the action of alcohol solution or hydrogen chloride gas, the desired pyrrole compound can be obtained through reaction. This conventional method needs to prepare an alcoholic solution of hydrogen chloride or needs to use hydrogen chloride gas, which is not convenient for industrial implementation and is difficult to be used in industrial production. Therefore, it is necessary to develop a process method that has sim...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 寇景平程三平林碧悦肖清波
Owner SUNSHINE LAKE PHARM CO LTD
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