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Preparation method of Tropifexor

A compound and reaction technology, applied in the field of preparation of Tropifexor, can solve problems such as difficult industrial production and high toxicity

Active Publication Date: 2021-08-24
武汉纽瑞斯医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the above reaction process, Tropifexor needs to be synthesized from compound (A) through a four-step reaction, and the highly corrosive Br 2 , the relatively toxic and expensive reagent t-BuONO, so it is difficult to realize industrial production by synthesizing Tropifexor according to this route

Method used

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  • Preparation method of Tropifexor
  • Preparation method of Tropifexor
  • Preparation method of Tropifexor

Examples

Experimental program
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Embodiment 1

[0057] The first step: the synthesis of 4-amino-3-fluoro-5-iodo-benzoic acid methyl ester

[0058]

[0059] Add 4-amino-3-fluorobenzoic acid methyl ester (20g, 118.24mmol), N-iodosuccinimide (40g, 177.79mmol,) into the reaction flask, add acetic acid (300mL) and stir the reaction at room temperature overnight.

[0060] Remove the solvent under reduced pressure, dilute with water, extract with ethyl acetate, combine the organic phases, and dry over anhydrous sodium sulfate; remove the solvent under reduced pressure, and the residue is separated by silica gel column chromatography (petroleum ether: ethyl acetate (v / v) =50:1) to obtain 4-amino-3-fluoro-5-iodo-benzoic acid methyl ester (33 g, yield 94.593%) as an ocher solid.

[0061] The second step: 2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo [3.2.1] Octane-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylic acid methyl ester

[0062]

[0063] 4-(((1R,5S)-8-azabicyclo[3.2.1]octane-3-yl...

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Abstract

The invention discloses a method for preparing a compound as shown in a formula (I). The method comprises the step of reacting a compound as shown in a formula (II), a compound as shown in a formula (III) and carbon disulfide in an organic solvent, wherein in the formula (I), R1 is H, D, OCF3, OCHF2, CF3, F, Cl, Br, C1-6 alkyl and C1-6 alkoxy; R2 is H, D, F, Cl, Br, a C1-6 alkyl group or a C1-6 alkoxy group; and R3 is H or C1-6 alkyl. The method has the advantages of short steps, cheap raw materials, mild conditions, high total yield and small influence on operators and environment, and is especially suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of Tropifexor. Background technique [0002] Tropifexor, chemical name 2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-aza Bicyclo[3.2.1]octane-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylic acid, its structural formula is as follows: [0003] [0004] Farnesoid X receptor (FXR) is a member of the nuclear hormone receptor superfamily, mainly expressed in the liver, kidney and intestine (Seol et al. Mol.Endocrinol (1995), 9:72-85; Forman et al. Cell( 1995), 81:687-693). It acts as a heterodimer with the retinoic acid X receptor (RXR) and binds to response elements in target gene promoters to regulate gene transcription. The FXR-RXR heterodimer binds with the highest affinity to the inverted repeat-1 (IR-1) response element, where the hexamers that bind the consensus receptor are separated by one nucleotide. FXR is p...

Claims

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Application Information

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IPC IPC(8): C07D451/02
CPCC07D451/02
Inventor 成冠军柯晓丹王进涛欧贤飞
Owner 武汉纽瑞斯医药科技有限公司
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