Method for preparing Brexpiprazole with one-pot process

A compound and alcohol solvent technology is applied in the field of preparation of Brexpiprazole to achieve the effects of solving insufficient reaction, simplifying the operation process and reducing environmental pollution

Active Publication Date: 2015-11-18
HANGZHOU XINBOSI BIOMEDICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, DMF is a nitrogen-containing solvent with a high boiling point. Generally, post-tre

Method used

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  • Method for preparing Brexpiprazole with one-pot process
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  • Method for preparing Brexpiprazole with one-pot process

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Experimental program
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Embodiment 1

[0045] Preparation of Brexpiprazole

[0046] Add compound (I) 7-hydroxy-2-quinolone (10.0 g, 62 mmol), 120 ml of ethanol and potassium carbonate (19.0 g, 138 mmol) into a 500 ml reaction flask. Compound (II) 1-bromo-4-chlorobutane (12.0 g, 70 mmol) was added under stirring, and the temperature was raised to reflux and stirred for 2 hours. Add 100ml of water and compound (IV) 1-(benzo[b]thiophen-4-yl)piperazine hydrochloride (15.0g, 59mmol), and continue to reflux and stir for 9 hours. Evaporate part of the solvent, lower the temperature to 50°C, add 40ml of ethyl acetate and stir for 0.5 hours, then continue to cool down to below 20°C, filter under reduced pressure, wash the filter cake with 20ml of ethanol three times, and dry it in a blast drying oven at 70°C for 3 hours . 14.5 g of Brexpiprazole (compound V) was obtained with a molar yield of 54%, which was basically the same as the molar yield of 55% in the method described in Route 2.

[0047] 1 HNMR(400MHz,dmso)δ11.5...

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Abstract

The invention relates to a method for preparing Brexpiprazole with a one-pot process. 7-hydroxyl-2-quinolone reacts with added 1-bromine-4-chlorobutane in the presence of alcohol and alkali, 1-(benzo[B]thiophen-4-yl) piperazine hydrochloride and water are added for a further reaction, finally, filtration, separation and drying are performed, and Brexpiprazole is obtained. Compared with the prior art, the method has the benefits as follows: 1, the problems of insufficient reaction and difficulty in purification in the prior art are solved; 2, the operation process is simplified, and the production efficiency is greatly improved; 3, used solvents are safe, and less environment pollution is caused.

Description

technical field [0001] The invention relates to a preparation method of Brexpiprazole, in particular to a method for preparing Brexpiprazole with a one-pot method. technical background [0002] Brexpiprazole, the structural formula is , the chemical name is 7-(4-(4-(benzo[b]thiophen-4-yl)-piperazin-1-yl)butoxy)-1H-quinolin-2-one. [0003] On July 14, 2014, Lundbeck Pharmaceuticals of Denmark and Otsuka Pharmaceuticals of Japan submitted a new drug application (NDA) for brexpiprazole to the U.S. Food and Drug Administration (FDA), which was approved by the FDA on July 10, 2015. The drug is indicated for the adjunctive treatment of major depressive disorder and schizophrenia. [0004] Brexpiprazole is a serotonin-dopamine activity modulator (SDAM) that acts on dopamine D2 and 5-HT2A receptors, has broad activity in multiple monoamine systems, and has reduced partial agonist activity on dopamine D2 receptors , and the affinity for specific 5-HT receptors (such as 5-HT1A, 5-...

Claims

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Application Information

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IPC IPC(8): C07D409/12
CPCC07D409/12
Inventor 杜焕达丁建圣叶鑫杰王振宇陈宇王万青韩璐刘艳华
Owner HANGZHOU XINBOSI BIOMEDICAL CO LTD
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