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Technological improvement method for preparing trelagliptin succinate

A technology for improving the technology of troxagliptin succinate and process, which is applied in the field of preparation of troxagliptin succinate, can solve problems such as unsuitability for industrialized production, complicated process routes, and insufficient environmental protection of solvents, and achieve the goal of overcoming cumbersome industrial operations and simplifying the process. The effect of operation process and environmental pollution is small

Active Publication Date: 2017-01-04
HANGZHOU XINBOSI BIOMEDICAL CO LTD
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

This literature report has the following disadvantages: the process route is relatively complicated, the solvent used is not environmentally friendly, and is not suitable for industrial production

Method used

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  • Technological improvement method for preparing trelagliptin succinate
  • Technological improvement method for preparing trelagliptin succinate
  • Technological improvement method for preparing trelagliptin succinate

Examples

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example 1

[0029] Example 1: One-pot method for preparing trexagliptin succinate

[0030] Add 15g of 6-chloro-3-methyluracil, 22.1g of 2-cyano-5-fluorobenzyl bromide and 150ml of ethanol into a 500ml three-necked flask. Add 39.3g NaHCO with stirring 3 , heated to reflux at 80°C for 3 hours. Add 24 g of (R)-3-aminopiperidine dihydrochloride and reflux at 80°C for 2 hours. Cool to 40°C, add 60ml of dichloromethane, and stir for 0.5 hours. After filtration, the filtrate was added to a 250ml three-neck flask, 16.6g of succinic acid was added, and heated to reflux at 80°C for 1 hour. Stir and cool overnight, filter, and put the filter cake into a blast drying oven to dry at 60°C to obtain 28.6 g of off-white crystalline powder (Trexagliptin succinate, compound V), with a yield of 64% and a purity of 99% by HPLC. See attached figure 1 ,Data are as follows:

[0031] 1H NMR (400 MHz, dmso) δ 8.87 (s, 3H), 7.92 (dd, J = 8.4, 5.6 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 7.14 (d, J = 9.0 Hz , 1H)...

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Abstract

The invention relates to a technological improvement method for preparing trelagliptin succinate (compound V). The method comprises the following steps: by taking 6-chloro-3-methyluracil in formula (I) shown in the description and 2-cyano-5-fluorobenzyl in formula (II) shown in the description as raw materials, carrying out bromo benzyl condensation reaction to obtain a compound III, selecting an appropriate solvent and control reaction condition, enabling a midboy III to be directly subjected to piperidine condensation reaction with (R)-3-aminopiperidine dihydrochloride shown in formula (IV) without separation and purification, and finally carrying out a salifying one-pot method to prepare trelagliptin succinate (compound V). Trelagliptin succinate is prepared by using the one-pot method, so that the reaction steps are reduced, the operation process is simplified, the production efficiency is improved, and the method is safe, environmentally friendly and suitable for the industrialized production.

Description

technical field [0001] The invention relates to the technical field of preparation methods of trexagliptin succinate. Background technique [0002] Trelagliptin succinate, chemical name 2-[6-(3R-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-di Hydrogen-2H-pyrimidin-1-ylmethyl]-4-fluoro-benzonitrile succinate, developed by Takeda Corporation of Japan, was approved for the treatment of type 2 diabetes in Japan on March 26, 2015, and is the first A small molecule diabetes drug that can be administered once a week has good curative effect, no drug resistance and high safety. [0003] There are not many preparation methods of trexagliptin succinate reported in existing literature, wherein CN1926128A The preparation method of trexagliptin succinate reported above is the most commonly used process method at present, and its route is as follows: [0004] [0005] The process is to condense 6-chloro-3-methyluracil (compound I) with 2-cyano-5-fluorobenzyl bromide (compound II) in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 杜焕达何永富刘艳华
Owner HANGZHOU XINBOSI BIOMEDICAL CO LTD
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