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Preparation method of indacaterol intermediate

A technology of intermediates and compounds, applied in the field of preparation of pharmaceutical intermediates, can solve the problems of high price, difficult industrial production, poor economy and environmental friendliness, and achieve the effect of good selectivity and simple operation

Inactive Publication Date: 2018-11-06
成都伊诺达博医药科技有限公司
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Problems solved by technology

[0005] The above-mentioned route has the following disadvantages: 1. a very expensive raw material is used: o-diethylbenzene (10,000 yuan / kg); 2. a large amount of isomers are generated in the second step cyclization reaction, which is not easy to adopt conventional methods Separation and purification need to be purified by column chromatography; ③ a large amount of sulfuric acid and acetic acid are used as solvents in the synthesis process, the economy and environmental friendliness are not good, and it is difficult for industrial production

Method used

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  • Preparation method of indacaterol intermediate
  • Preparation method of indacaterol intermediate
  • Preparation method of indacaterol intermediate

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Embodiment 1

[0026] Embodiment 1, preparation of indacaterol intermediate 5,6-diethyl-2,3-dihydro-1H-indene-2-amine hydrochloride

[0027]

[0028] (1) Synthesis of N-(2,3-dihydro-1H-inden-2-yl)acetamide (compound 2)

[0029] Add compound 1 (100g, 0.751mol) and dichloromethane (700ml) into a 2L three-necked flask, then add triethylamine (189.6g, 1.877mol), control the temperature below 10°C, add acetyl chloride (64.9g, 0.827mol), after the addition, the temperature was raised to room temperature for 2 hours, and TLC monitored the reaction to be complete. Add 2N hydrochloric acid (200ml) to quench the reaction, separate the layers, wash the organic phase with tap water (150ml×2), and dry over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 126.8 g of white solid (compound 2), with a yield of 96.3%.

[0030] (2) Synthesis of N-(5-acetyl-2,3-dihydro-1H-inden-2-yl)acetamide (compound 3)

[0031] Add aluminum trichloride (106.7g, ...

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Abstract

The invention provides a preparation method of an indacaterol intermediate. According to the preparation method provided by the invention, low-price raw materials are adopted, the operation is simpleand feasible, the reaction selectivity is good, complicated operations such as column chromatography are not required, the yield of a final prepared product is as high as 92.6%, and the total yield ofa whole route is as high as 71.2%, so that the preparation method is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the preparation of pharmaceutical intermediates, in particular to a preparation method of indacaterol intermediates. Background technique [0002] Indacaterol (Indacaterol), the chemical name is (R)-5-[2-(5,6-diethyldihydroinden-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H -Quinolin-2-one, a bronchodilator drug developed by Novartis in Switzerland, is a new type of ultra-long-acting β2 receptor agonist, which can quickly, effectively and durably control the symptoms of patients with chronic obstructive pulmonary disease (COPD), improve Pulmonary function, suitable for maintenance treatment of stable adult COPD patients. [0003] The structural formula of indacaterol is as follows: Among them, 5,6-diethyl-2,3-dihydro-1H-inden-2-amine As its key intermediate, the synthesis route of this compound reported in the literature is as follows (J.Med.Chem.2010,53,3675-3684; US7622483B2,2009): [0004] [0005] The above-mentioned rou...

Claims

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Application Information

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IPC IPC(8): C07C211/42C07C209/62
CPCC07C209/62C07C231/02C07C231/12C07C2602/08C07C233/06C07C233/32C07C211/42
Inventor 付清泉张菊华林强刘正超王建陈志勇蔡丰骏
Owner 成都伊诺达博医药科技有限公司
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