Method for preparing imidafenacin

A technology of midanacin and methylimidazole, which is applied in the field of drug synthesis, can solve the problems of low safety, blindness, unfriendly to the human body and the environment, and achieve the effect of being friendly to the human body and the environment

Active Publication Date: 2014-05-07
JIANGZI QINGFENG PHARMACEUTICALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] Hydrogen peroxide solution is used in this method, but hydrogen peroxide solution has strong oxidizing properties and is corrosive to a certain extent. Inhalation of the vapor or mist is

Method used

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  • Method for preparing imidafenacin

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0032] Example 1: Preparation of 4-bromo-2,2-diphenylbutyronitrile

[0033] Add 400 mL of dry tetrahydrofuran to a 2L reaction flask, add 60% sodium hydride (82.8 g, 2.06 mol) under nitrogen protection, and stir to obtain a gray turbid liquid A. Fully dissolve diphenylacetonitrile (200g, 1.04mol) and 1,2-dibromoethane (204.2g, 1.08mol) with 400mL of dry tetrahydrofuran solution to obtain a colorless clear liquid B; at 5~15℃, the solution B was dropped into the turbid liquid A, and the reaction was kept at 10-15°C for 6 hours. After the reaction was detected by TLC, a small amount of water was dropped into the reaction system until no bubbles were generated. Then, 800 mL of water and 400 mL of ethyl acetate were added and stirred for liquid separation, the organic layer was washed with water and saturated sodium chloride solution, the organic layer was dried with anhydrous sodium sulfate, filtered with suction, and concentrated under reduced pressure to obtain 310 g of yellow liqu...

Embodiment 2

[0036] Example 2: Preparation of 4-bromo-2,2-diphenylbutanamide

[0037] Add 4-bromo-2,2-diphenylbutyronitrile (150g, 0.5mol), 750mL 6mol / L KOH solution, 750mL dimethyl sulfoxide to a 3L reaction flask, and heat to 100~120℃ and stir to react. 1h, after TLC detects that the reaction is completed, the temperature is lowered to 40°C, 2000mL water and 2000mL dichloromethane are added, and the mixture is separated. The organic layer is washed with water, saturated sodium bicarbonate and sodium chloride solution, separated and dried with anhydrous sodium sulfate. The organic layer was filtered with suction and concentrated under reduced pressure to obtain 161.92 g of brown oily liquid with a yield of 96%.

[0038]

Embodiment 3

[0039] Example 3: Preparation of 4-bromo-2,2-diphenylbutanamide

[0040] Add 4-bromo-2,2-diphenylbutyronitrile (150g, 0.5mol), 666mL 6mol / L NaOH solution, and 750mL dimethyl sulfoxide into a 3L reaction flask. Heat to 100~120℃ and stir to react. 1h, after TLC detects that the reaction is completed, the temperature is lowered to 40°C, 2000mL water and 2000mL dichloromethane are added, and the mixture is separated. The organic layer is washed with water, saturated sodium bicarbonate and sodium chloride solution, separated and dried with anhydrous sodium sulfate. The organic layer was filtered with suction and concentrated under reduced pressure to obtain 146.73 g of a brown oily liquid with a yield of 87%.

[0041]

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Abstract

The invention discloses a method for preparing imidafenacin. The method comprises the steps of hydrolyzing 4-bromo-2,2-diphenyl butyronitrile into acid amide under an alkaline condition, and then enabling the acid amide to react with 2-methylimidazole so as to obtain a target product. The preparation method provided by the invention is high in yield, economical, simple, convenient, friendly to human body and environment, and suitable for industrialized large-scale production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a new method for preparing midanacin. [0002] Background technique [0003] Symptomatic overactive bladder (OAB) is a common chronic lower urinary tract dysfunction, which is defined by the International Anti-Urinary Incontinence Society (ICS) syndrome characterized by urinary incontinence and urge incontinence. [0004] The incidence rate of OAB is relatively high. The incidence rate of men over 75 years old in European and American countries is as high as 42%, and the incidence rate of women is slightly lower at 31%. The incidence rate of men over 50 years old in Beijing in China is as high as 16.4%. The overall incidence of incontinence and urge incontinence is 40.4%, which seriously affects the physical and mental health of patients and reduces the quality of life. There is no specific treatment for OAB in the past, and anticholinergic drugs, calcium channel blo...

Claims

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Application Information

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IPC IPC(8): C07D233/56
CPCC07D233/56
Inventor 谢宁杨小玲蔡鸿飞邵秀芬程帆付敏熊先水沈曦何党军崔刚
Owner JIANGZI QINGFENG PHARMACEUTICALS INC
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