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Fluorine group-containing-modified dabigatran etexilate analogue and synthetic method thereof

A dabigatran etexilate and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of high price, increased preparation cost of dabigatran etexilate analogues, increased risk of preparation process, etc.

Inactive Publication Date: 2013-09-11
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Two of the purpose of the present invention is in order to solve the above-mentioned preparation method of dabigatran etexilate analogues using expensive metal Pd / C catalytic reduction reagent, volatile and toxic HCl, NH 3 etc. gas, thereby increasing the preparation cost of dabigatran etexilate analogues, and technical problems such as increased danger of the preparation process to provide a safe, reliable, simple synthesis process, relatively low synthesis cost fluorine-containing group modified The synthetic method of dabigatran etexilate analog

Method used

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  • Fluorine group-containing-modified dabigatran etexilate analogue and synthetic method thereof
  • Fluorine group-containing-modified dabigatran etexilate analogue and synthetic method thereof
  • Fluorine group-containing-modified dabigatran etexilate analogue and synthetic method thereof

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Embodiment 1

[0057] A fluorine-containing modified dabigatran etexilate analogue, namely 3-[[[2-[[[4-[[[(hexyloxy)carbonyl] amino] iminomethyl] phenyl] amino] methyl Base]-1-ethyl-1H-benzimidazol-5-yl]carbonyl](4-fluorophenyl)amino]propionic acid ethyl ester, that is, 4-trifluoroaniline as raw material, synthesized through 9 steps , the final product contains fluorine-modified dabigatran etexilate analogs, i.e. 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino] Methyl]-1-ethyl-1H-benzimidazol-5-yl]carbonyl](4-fluorophenyl)amino]ethyl propionate, the synthetic reaction process schematic diagram is as follows Figure 4 As shown, each step of synthesis reaction is as follows:

[0058] (1), Synthesis of ethyl 3-(4-fluorophenylamino)propionate

[0059] Add 4-fluoroaniline (5.57g, 50.0mmol), ethyl 3-bromopropionate (16.45g, 90.0mmol) and triethylamine (21.0mL) into a round bottom flask, toluene as solvent, and react at 100°C for 12h Obtain reaction solution 1;

[0060] The 4-f...

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Abstract

The invention discloses a fluorine group-containing-modified dabigatran etexilate analogue, namely 3-[[[2-[[[4-[[[(hexaoxy)carbonyl]methylenamino]phenyl]amino]methyl]-1-ethyl-1H-benzimidazole-5-radical]carbonyl](4-fluorophenyl)amino]ethyl propionate, and a synthetic method thereof. The fluorine group-containing-modified dabigatran etexilate analogue is synthesized finally through serial reaction by taking fluorine group-containing amino compound 4-fluoroaniline as a starting raw material. The synthetic method of the fluorine group-containing-modified dabigatran etexilate analogue has the advantages of being simple to operate, easily available for reagents, relatively lower for synthetic cost, capable of reducing the danger in synthetic process, higher in yield during synthetic steps, short in synthetic time and the like.

Description

technical field [0001] The invention relates to a dabigatran etexilate analogue modified by a fluorine-containing group and a synthesis method thereof, belonging to the field of chemical synthesis. Background technique [0002] The direct thrombin inhibitor dabigatran etexilate (dabigatrau etexilate, trade name Pradaxa) was developed by Boehringer Ingelheim, Germany, and was first launched in Germany and the UK in April 2008. It is a new type, non-peptide, competitive , a reversible thrombin inhibitor, after being taken orally and absorbed by the gastrointestinal tract, it will be converted into dabigatran with direct anticoagulant activity in the body, and its structural diagram is shown in figure 1 shown. [0003] The structural representation of dabigatran etexilate is as follows: figure 2 As shown, dabigatran etexilate is the first new category of oral anticoagulant drugs listed on the market in 50 years after warfarin. Medication monitoring, less drug interactions a...

Claims

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Application Information

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IPC IPC(8): C07D235/14C07D401/12
Inventor 任玉杰王庆伟陈海峰
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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