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Mosapride impurity compound

A technique for mosapride citrate and compounds, which is applied in the field of drug synthesis, can solve the problems affecting the quality of mosapride citrate raw materials and difficult purification, and achieve short routes, high product purity and high reaction yield high effect

Pending Publication Date: 2021-12-17
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Since the brominated impurity is similar in structure to the chlorinated product 3, it is difficult to separate it in the subsequent separation and purification, and it is even difficult to detect it by conventional methods, and the impurity compound I will continue to participate in subsequent reactions. If the body impurities are not studied and controlled, it will bring difficulties to the subsequent purification, and ultimately affect the quality of mosapride citrate API. The preparation method of the bromide impurity provides a qualified reference substance, which can play a positive role in the quality control of mosapride citrate
[0010] At present, there is no literature report on the preparation method of the brominated impurity of mosapride citrate. Therefore, a process with low production cost, simple operation and higher yield is explored for the brominated impurity of mosapride citrate. Routing is still a problem to be solved for now

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add ethyl 2-ethoxy-4-acetamidobenzoate (25.13g, 0.1mol) and NBS (23.14g, 0.13mol) into DMF (120mL), heat at 70°C for 3h, and detect the reaction Pour the reaction solution into ice water and stir to crystallize, filter, wash the filter cake with water (50ml×2), and dry to obtain ethyl 2-ethoxy-4-acetamido-5-bromobenzoate as a white solid with a yield of 98.7% , with a purity of 99.95%.

Embodiment 2

[0045] Add ethyl 2-ethoxy-4-acetamidobenzoate (25.13g, 0.1mol) and NBS (17.80g, 0.1mol) into methanol (120mL), heat at 50°C for 3h, and detect the reaction Pour the reaction solution into ice water and stir to crystallize, filter, wash the filter cake with water (50ml×2), and dry to obtain ethyl 2-ethoxy-4-acetamido-5-bromobenzoate as a white solid with a yield of 94.2% , with a purity of 99.85%.

Embodiment 3

[0047] Add ethyl 2-ethoxy-4-acetamidobenzoate (25.13g, 0.1mol) and NBS (32.04g, 0.18mol) into acetonitrile (120mL), heat at 80°C for 3h, and detect the reaction Pour the reaction solution into ice water and stir to crystallize, filter, wash the filter cake with water (50ml×2), and dry to obtain ethyl 2-ethoxy-4-acetamido-5-bromobenzoate as a white solid with a yield of 93.4% , with a purity of 99.76%.

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a mosapride impurity compound. The mosapride impurity compound provided by the invention is 2-ethoxy-4-acetamido-5-bromobenzoic acid ethyl ester. The preparation method of the impurity comprises the following steps of: adding ethyl 2-ethoxy-4-acetaminobenzoate and N-bromosuccinimide (NBS) into an organic solvent, and carrying out temperature-controlled stirring reaction to obtain 2-ethoxy-4-acetamido-5-bromobenzoic acid ethyl ester. Meanwhile, the invention further provides a method for preparing a mosapride citrate brominated impurity compound VI from the impurity compound. The magazine compound provided by the invention can be used as an impurity reference substance for detecting mosapride citrate intermediates, bulk drugs and / or preparations in the production process. The synthesis method provided by the invention is short in route and simple to operate.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a mosapride impurity compound. Background technique [0002] Mosapride citrate (mosapride citrate), the chemical name is 2-ethoxy-4-amino-5-chloro-N-[[4-[(4-fluorophenyl)-methyl]morpholine- 2-yl]methyl]benzamide citrate dihydrate is a digestive tract prokinetic drug developed by Dainippon Pharmaceutical Co., Ltd., which is a selective serotonin 4 receptor agonist; it was first released in June 1998 Listed in Japan, it is mostly used clinically for the treatment of chronic gastritis with burning, nausea, vomiting and other gastrointestinal diseases. It has the advantages of strong receptor selectivity, small dose, safety and high efficiency. Its structure is as follows: [0003] [0004] The bulk drug of mosapride citrate is already on the market, and the preparation method for this bulk drug is to combine two important side chains, 2-ethoxyl-4-amino-5-chlorobenzoic aci...

Claims

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Application Information

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IPC IPC(8): C07C233/54C07C231/12C07D265/30C07C51/41C07C59/265
CPCC07C233/54C07C231/12C07D265/30C07C51/412C07C59/265
Inventor 高佃台臧超刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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