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New benzocyclobutane, preparation method thereof and application thereof

A technology for separation and purification of compounds, applied in the preparation of organic compounds, preparation of aminohydroxyl compounds, chemical instruments and methods, etc., can solve problems such as low yield and difficulty in industrialization, and achieve high yield, high optical purity, and resolution Effect of Yield Improvement

Inactive Publication Date: 2012-08-15
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] In view of the low yield and difficulty in industrialization of the existing (1S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane synthesis method, the present invention provides a preparation process A new preparation method of (1S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane that is simple, high in yield and low in cost and suitable for industrial production, and provides A new intermediate for the synthesis of (1S)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane

Method used

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  • New benzocyclobutane, preparation method thereof and application thereof
  • New benzocyclobutane, preparation method thereof and application thereof
  • New benzocyclobutane, preparation method thereof and application thereof

Examples

Experimental program
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Embodiment

[0048] Embodiment (1S)-4, the synthesis of 5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane oxalate

[0049] Step A: Synthesis of I-2 (4,5-dimethoxy-1-carboxy-benzocyclobutane)

[0050] 4,5-dimethoxy-1-cyano-benzocyclobutane (200g, 1.04mol), potassium hydroxide (1000g, 18mol) and ethanol (4000ml) were mixed, stirred and refluxed for 5 hours, and the reaction ended . Cool down to room temperature naturally, add water (10 L) to dissolve, evaporate ethanol under reduced pressure, acidify with concentrated hydrochloric acid, extract with ethyl acetate (1000ml×3), combine the extracts, dry over anhydrous sodium sulfate, decolorize with activated carbon, evaporate the solvent under reduced pressure, Washed with ethyl acetate (600ml) and dried to obtain 208g of the title compound with a yield of 95%. mp137—138°C. TLC: dichloromethane:methanol=10:1, Rf value=0.4.

[0051] Step B: Synthesis of I-3 ((1S)-4,5-dimethoxy-1-carboxy-benzocyclobutane)

[0052] Step B-1: Mix the compoun...

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Abstract

The invention provides a preparation method for (1S)-4, 5-dimethoxy-1-(methyl-amino-methyl)-benzocyclobutane serving as a key intermediate of ivabradine hydrochloride and addition salt thereof, and meanwhile provides a method for preparing an intermediate of the (1S)-4, 5-dimethoxy-1-(methyl-amino-methyl)-benzocyclobutane and a method for splitting the intermediate.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new benzocyclobutane, its preparation method and application. [0002] More specifically, the present invention relates to a compound of formula I-1 in a new (S) configuration and a synthesis method thereof. The structural formula of the compound of formula I-1 is as follows: [0003] [0004] The compound of formula I-1 obtained according to the method of the present invention is an important starting material for the compound of synthetic formula I, and the compound of said formula I is an important intermediate of formula II ivabradine hydrochloride: [0005] Background technique [0006] The chemical name of ivabradine hydrochloride is 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]oct-1,3,5-trien-7-yl] Methyl}(methyl)-amino]propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one hydrochloride , is a selective and specific If channel blocker developed by Servier, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/40C07C231/02C07C217/48C07C213/02C07D223/16
Inventor 刘昕蔡瞻杨玉社黄海燕李纬叶海储刚钟雪彬
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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