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The preparation method of anseltrapib

A technology of general formula and compound, applied in organic chemistry and other directions, can solve the problems of high preparation cost and low yield of final product, and achieve the effects of simple post-processing method, few reaction by-products, and mild reaction conditions.

Active Publication Date: 2018-06-19
湖南千金湘江药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of the final product is on the low side, and the preparation cost of the final product is relatively high

Method used

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  • The preparation method of anseltrapib
  • The preparation method of anseltrapib
  • The preparation method of anseltrapib

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Experimental program
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Embodiment 1

[0039] Step 1: Add compound II, compound III, acetonitrile and 3MK to a 100 mL flask equipped with a reflux condenser 2 CO 3 . The resulting biphasic solution was bubbled with nitrogen for 5 minutes. The catalyst Pd(PPh3)4 was added under the protection of nitrogen, the reaction temperature was raised to 80° C., and stirred for 3-4 hours under the protection of nitrogen. After the completion of the reaction was monitored by TLC, the reaction mixture was cooled to room temperature and the two phases were separated. The layers were separated, the organic layer was collected, washed 1-2 times with saturated brine, activated carbon (0.20 g) was added to the organic layer, stirred at room temperature for 1 hour, and then the mixture was filtered through celite. A small amount of acetonitrile was added to the filtrate for azeotropic drying to obtain a pale yellow oil. That is intermediate IV. Yield 70%.

[0040]

[0041] Step 1 coupling reaction feed ratio

[0042]

[00...

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Abstract

The preparation method of the compound of formula (I), it comprises: 1) by 2-chloro-5-trifluoromethyl-aniline (II) and (4-fluoro-5-isopropyl-2-methoxyphenyl ) boronic acid (III) reacts to obtain 2-(4-fluoro-5-isopropyl-2-methoxyphenyl)-5-trifluoromethyl-aniline (general formula IV); 2) by the general formula (IV) compound reacts with tert-butyl nitrite, acetaldehyde and base to obtain 2-(4-fluoro-5-isopropyl-2-methoxyphenyl)-5-trifluoromethyl-benzyl Alcohol (general formula V); 3) react by general formula (V) compound and halogenating reagent, then add (4S,5R)-5-[3,5-bis(trifluoromethyl)benzene in the reaction mixture Base]-4-methyl-1,3-oxazolidin-2-ketone (VI) is reacted to obtain (4S,5R)-5-[3,5-bis(trifluoromethyl) of formula (I) )phenyl]-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl Base-1,3-oxazolidin-2-one (i.e. ansertrapib).

Description

technical field [0001] The present invention relates to ansertrapib, namely (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-5'-isopropyl-2 A method for preparing '-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one. Background technique [0002] Atherosclerosis and its clinical consequences, coronary heart disease (CHD), stroke, and peripheral vascular disease threaten human health. [0003] It has long been recognized that, in mammals, changes in the distribution of circulating lipoproteins are associated with the risk of atherosclerosis and CHD. The clinical success of HMG-CoA reductase inhibitors, particularly statins, in reducing coronary events is based on reducing circulating low-density lipoprotein cholesterol (LDL-C), levels of which are directly related to increased atherosclerotic risk . Recently, epidemiological studies have shown an inverse relationship between high-density lipoprotein cholesterol (HDL-C) levels and atheros...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/22
Inventor 金秉德姚亮元王琼瑶田瑶司马颖钰
Owner 湖南千金湘江药业股份有限公司