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Silodosin intermediate preparing method

A technology for silodosin and intermediates, which is applied in the field of preparation of silodosin intermediates, can solve the problems of potential safety hazards in industrial production, low total yield of routes, serious production pollution, etc., and achieve stable properties of intermediate substances and yield The effect of high efficiency and low equipment requirements

Inactive Publication Date: 2019-04-05
ANHUI QINGYUN PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although this route is relatively novel in the design of the route, the total yield of the route is low. During the azidation reaction, there are potential safety hazards in industrial production. In addition, palladium- Barium sulfate is used as a catalyst, and the cost is relatively high
[0015] In summary, the current synthesis of silodosin intermediate compound 1 is either due to serious production pollution, high production costs due to production yield, or difficult to achieve industrialization due to the use of expensive chemical reagents. Production, therefore the preparation method of the synthetic silodosin intermediate compound 1 that develops green, environmental protection, strong maneuverability has broad prospect

Method used

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Effect test

Embodiment 1

[0097] A method for preparing silodosin intermediate, said method comprising the steps of:

[0098] S1. Alkylation reaction of 5-bromoindoline solution and triethylamine to obtain substance A;

[0099] S2, performing a substitution reaction on the solution of substance A, bromoacetone, and a catalyst to obtain substance B;

[0100] S3, subjecting the solution of substance B, the catalyst, and the reducing agent to amination reaction to obtain substance C;

[0101] S4, performing bromination reaction on the solution of substance C and N-bromosuccinimide solution to obtain substance D;

[0102] S5, subjecting the solution of substance D and cuprous cyanide to cyanation reaction to obtain substance E;

[0103] S6. After the solution of substance E and the catalyst are subjected to hydrogenolysis reaction, a tartrate salt is formed to obtain a silodosin intermediate.

Embodiment 2

[0105] A method for preparing silodosin intermediate, said method comprising the steps of:

[0106] S1. Alkylation reaction of 5-bromoindoline solution and triethylamine to obtain substance A;

[0107] S2, performing a substitution reaction on the solution of substance A, bromoacetone, and a catalyst to obtain substance B;

[0108] S3, subjecting the solution of substance B, the catalyst, and the reducing agent to amination reaction to obtain substance C;

[0109] S4, performing bromination reaction on the solution of substance C and N-bromosuccinimide solution to obtain substance D;

[0110] S5, subjecting the solution of substance D and cuprous cyanide to cyanation reaction to obtain substance E;

[0111] S6. After the solution of substance E and the catalyst are subjected to hydrogenolysis reaction, the tartrate is formed to obtain the silodosin intermediate;

[0112] Among them, the specific method of S1 is: mix 5-bromoindoline solution and triethylamine, heat up, keep ...

Embodiment 3

[0122] A method for preparing silodosin intermediate, said method comprising the steps of:

[0123] S1. Alkylation reaction of 5-bromoindoline solution and triethylamine to obtain substance A;

[0124] S2, performing a substitution reaction on the solution of substance A, bromoacetone, and a catalyst to obtain substance B;

[0125] S3, subjecting the solution of substance B, the catalyst, and the reducing agent to amination reaction to obtain substance C;

[0126] S4, performing bromination reaction on the solution of substance C and N-bromosuccinimide solution to obtain substance D;

[0127] S5, subjecting the solution of substance D and cuprous cyanide to cyanation reaction to obtain substance E;

[0128] S6. After the solution of substance E and the catalyst are subjected to hydrogenolysis reaction, the tartrate is formed to obtain the silodosin intermediate;

[0129] Among them, the specific method of S1 is: mix 5-bromoindoline solution and triethylamine, heat up, keep ...

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Abstract

The invention discloses a silodosin intermediate preparing method. The silodosin intermediate preparing method comprises the following steps of S1, subjecting 5-bromoindoline solution and triethylamine to alkylation reaction to obtain a material A; S2, subjecting solution of the material A, bromacetone and catalysts to substitution reaction to obtain a material B; S3, subjecting the solution of the material B, catalysts and reducing agent to amination to obtain a material C; S4, subjecting the solution of the material C and N-bromosuccinimide solution to bromination reaction to obtain a material D; S5, subjecting the solution of the material D and cuprous cyanide to cyanation to obtain a material E; S6, subjecting the solution of the material E and catalysts to hydrogenolysis to obtain a tartrate, namely, a silodosin intermediate. The silodosin intermediate preparing method is simple, high in yield, low in energy consumption, green and environmentally friendly; the prepared silodosin intermediate is high in quality and applicable to large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a method for preparing a silodosin intermediate. Background technique [0002] Silodosin is an α-adrenoceptor antagonist invented by Kissei Pharmaceutical Company of Japan, which has a very good therapeutic effect on urinary disorders related to benign prostatic hyperplasia. [0003] At present, the synthesis of silodosin is mainly synthesized from the intermediate described in compound 1 through multi-step reactions, as shown in Reaction Formula 1. [0004] [0005] There are many synthetic routes about the silodosin intermediate compound 1, and the literature reports mainly contain the following types: One, Japanese Patent JP2001199956 reports a synthetic route using benzoic acid, indoline, etc. as starting materials, such as reaction formula 2 shown. [0006] [0007] The route is long, the yield is low, and the phosphides produced have a great impact on t...

Claims

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Application Information

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IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 黄欢黄庆国韩明超
Owner ANHUI QINGYUN PHARMA & CHEM
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