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Preparation method of (s)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propanamide and salts thereof

A technology of fluorobenzyloxy and fluorobenzyl, which is applied in the preparation of carboxylic acid amides, carbon-based compounds, organic compounds, etc., and can solve the problems that the yield and purity are difficult to be guaranteed.

Active Publication Date: 2019-03-08
ZHEJIANG MENOVO PHARMA
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  • Claims
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Problems solved by technology

Therefore, the research on impurities 10 and 11 is very important, but there are relatively few literature reports on the synthesis methods of the above impurities, and the yield and purity are difficult to be guaranteed.

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  • Preparation method of (s)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propanamide and salts thereof
  • Preparation method of (s)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propanamide and salts thereof
  • Preparation method of (s)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propanamide and salts thereof

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[0066] The present invention will be further described in detail below in conjunction with the accompanying drawings and embodiments.

[0067] The preparation method of (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propanamide of the present embodiment comprises the following steps:

[0068] (1) Add 3-bromo-4-hydroxybenzaldehyde (25g, 0.12mol), toluene (250mL), potassium carbonate (22.2g, 0.161mol), tetrabutylammonium bromide (20g, 0.062 mol), then feed nitrogen, and the resulting mixture was stirred at room temperature for 10 minutes;

[0069] Under the protection of nitrogen, m-fluorobenzyl bromide (23.5 g, 0.124 mol) was added dropwise to the above reaction mixture at room temperature within 1 hour. After the dropwise addition was completed, the mixture was slowly heated to 70-90°C and kept for 6 hours. In the reaction process, control the reaction progress by thin-layer chromatography (mobile phase is n-hexane and 10% ethyl acetate, under 254nm ultraviolet la...

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Abstract

The invention relates to a method for preparing (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide and salts thereof. Salts of (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide mean (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide mesylates. The preparation method comprises the step of preparing the target product through synthesizing novel compounds, i.e., 2-(3-bromo-4((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolane and 2-((3-fluorobenzyl)oxy)-5-formyl phenylboronic acid and belongs to bran-new preparation methods. The yield of the (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide prepared by the preparation method is 49.57%, and the HPLC purity reaches 78.92%, and the yield of the salts of the prepared (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide is 50.40%, and the HPLC purity reaches 96.35%, so that the yield and the HPLC purity are improved greatly compared with those in the prior art.

Description

technical field [0001] The invention relates to a preparation method of (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino]propionamide and salts thereof. Background technique [0002] Safinamide is a sodium channel blocker, calcium channel regulator, monoamine oxidase B (MAO-B) inhibitor, glutamate release inhibitor and dopamine metabolism regulator. In the prior art, two important impurities are involved in the process of preparing safinamide, which are (S)-2-[3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzylamino ] Propionamide (Compound 10) and its salts (Compound 11). [0003] [0004] Many drugs that currently exist are giving up research and development because of the unpredictable toxicity to the metabolism of the human body due to the existence of special impurities. According to the research on safinamide in the prior art, the above impurity shows extremely high toxicity to enzymes of the cytochrome P450 system. Therefore, the research on impurities 10 a...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/12C07C237/06
CPCC07C45/63C07C45/64C07C231/12C07D213/127C07D213/20C07D317/22C07F5/025C07C237/06C07C47/575
Inventor 林祖峰贾江南刘涛三迪普·萨达帕张立兵万光敏陈为人姚成志
Owner ZHEJIANG MENOVO PHARMA
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