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Preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethyl benzylamine

A technology of trifluoromethylbenzylamine and trifluoromethyl, applied in the preparation field of Elagolix intermediate 2-fluoro-6-trifluoromethylbenzylamine, can solve the problem of 2-fluoro-6-trifluoromethylbenzylamine The problems of expensive raw materials for amine synthesis, to achieve the effect of cheap raw materials, conducive to industrial production, and high purity

Inactive Publication Date: 2020-11-10
南京莱克施德药业有限公司
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Problems solved by technology

[0004] The technical problem to be solved by the present invention is: provide a kind of preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethylbenzylamine, it solves the problem that the synthetic raw material of 2-fluoro-6-trifluoromethylbenzylamine is expensive at present The problem

Method used

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  • Preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethyl benzylamine
  • Preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethyl benzylamine
  • Preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethyl benzylamine

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Embodiment

[0029] (1) 2-Fluoro-6-(trifluoromethyl)benzoic acid (e.g. figure 2 )Synthesis.

[0030] In a 2L four-neck flask equipped with a thermometer, mechanical stirring, and constant pressure dropping funnel device, add 50g (0.3mol) of 3-fluorobenzotrifluoride and 500ml of anhydrous tetrahydrofuran under nitrogen protection, and cool the liquid nitrogen to -78℃. Add 190.5ml (1.6M) of n-butyllithium dropwise, the temperature is controlled at -60~-65℃, after the addition is completed, the temperature is controlled at -60~-65℃, continue to stir for 5 hours, and pass carbon dioxide gas until The reaction was completed; a small amount of water was added to quench the reaction, and the reaction was raised to room temperature; hydrochloric acid was adjusted to pH 2, 500 ml of ethyl acetate was added, and the organic layer was separated; the organic layer was concentrated under reduced pressure to obtain 53 g of white solid, yield 85%, purity 98 %.

[0031] (2) 2-Fluoro-6-(trifluoromethyl)benzyl...

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Abstract

The invention discloses a preparation method of an Elagolix intermediate 2-fluoro-6-trifluoromethyl benzylamine, and belongs to the technical field of medical intermediates. The preparation method comprises the following steps: (1) synthesizing 2-fluoro-6-(trifluoromethyl) benzyl alcohol; (2) synthesizing 2-fluoro-6-(trifluoromethyl) benzyl alcohol; (3) synthesizing a 2-fluoro-6-(trifluoromethyl)benzenemethanesulfonate compound and a phthalimide compound; (4) directly synthesizing a phthalimide compound; (5) synthesizing the 2-fluorine-6-trifluoromethyl benzylamine. According to the preparation method, factors such as a reaction reagent and a reaction solvent are optimized, so the reaction conditions are mild, the technological process is simple and convenient, the requirements on equipment are relatively low, the price of raw materials is lower, the purity of the obtained product is high, and industrial production is facilitated.

Description

Technical field [0001] The invention relates to a preparation method of Elagolix intermediate 2-fluoro-6-trifluoromethylbenzylamine, and belongs to the technical field of pharmaceutical intermediates. Background technique [0002] AbbVie, English name is Elagolix, CAS: 834153-87-6, chemical name is (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro- 6-(trif luoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoic acid, elagolix has been granted by the FDA in October 2017 The NDA priority review qualification for the treatment of endometriosis is expected to be the first drug approved by the FDA for the treatment of endometriosis. [0003] Regarding the synthesis of AbbVie’s Elagolix intermediate 2-fluoro-6-trifluoromethylbenzylamine, the synthesis method disclosed in the world patent wo2007134862 uses 2-fluoro-6-(trifluoromethyl)benzonitrile as the starting material , Reduced with borane tetrahydrofuran complex to obtain 2-fluoro-6-trifl...

Claims

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Application Information

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IPC IPC(8): C07C209/62C07C211/29
CPCC07C51/15C07C29/147C07C303/28C07D209/48C07C209/62
Inventor 孙光明顾玉龙黄尔青李冉孙亚杰
Owner 南京莱克施德药业有限公司
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