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Method for preparing losartan side chain compound

A compound and product technology, applied in the field of preparation of sartan side chain compound, an important intermediate of sartan antihypertensive drugs, can solve the problems of expensive raw materials and catalysts, harsh reaction conditions, etc. safe effect

Active Publication Date: 2011-09-21
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the fact that such biphenyl compounds are all obtained by coupling Grignard reagent or phenylboronic acid with bromoarene (EP470794, EP0470795, US5310928, EP1777224, WO20060672150) the reaction conditions are harsh, and the raw materials and catalysts used are expensive

Method used

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  • Method for preparing losartan side chain compound
  • Method for preparing losartan side chain compound
  • Method for preparing losartan side chain compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of 5-[2-(4'-methylbiphenyl)]-2-H-imidazole

[0023] In a 250ml three-necked flask, add 25.2g (010mol) 5-[2-(4'-bromomethylbiphenyl)]-2-H-imidazole, 70ml tetrahydrofuran, 0.7g palladium carbon, stir for 30 minutes, and replace with nitrogen Air, then hydrogen, reacted at room temperature for 24 hours, the reaction was completed, and processed to obtain 5-[2-(4'-methylbiphenyl)]-2-H-imidazole with a yield of 84%.

[0024] 1 HNMR(CDCl3): 2.25(s, 3H), 6.95(d, 2H), 7.10(d, 2H), 7.50-7.70(m, 4H)

Embodiment 2

[0025] Embodiment 2: the synthesis of 5-[2-(4'-methylbiphenyl)]-2-H-imidazole

[0026] Other conditions remain unchanged, the solvent is changed from ethanol to ethyl acetate, and the yield is 70%

Embodiment 3

[0027] Embodiment 3: the synthesis of 5-[2-(4'-methylbiphenyl)]-2-triphenylmethyl-imidazole

[0028] In a 250ml three-necked flask, add 49.5g (010mol) 5-[2-(4'-bromomethylbiphenyl)]-2-H-imidazole, 210ml tetrahydrofuran, 0.7g palladium carbon, stir for 30 minutes, and replace with nitrogen Air, then hydrogen, reacted at room temperature for 24 hours, the reaction was completed, and processed to obtain 5-[2-(4'-methylbiphenyl)]-2-triphenylmethyl-imidazole with a yield of 70%.

[0029] 1 HNMR(CDCl3): 2.25(s, 3H), 6.90-7.00(m, 10H), 7.20-7.45(m, 12H), 7.85-7.90(m, 1H)

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Abstract

The invention relates to a method for preparing valsartan side-chain compounds, which comprises the steps as follows: the compounds of Structural Formula II or / and the compounds of Structural Formula III are dissolved in an organic solvent for hydrogen reduction under the function of a catalyst and at the temperature of 20 DEG C to 100 DEG C; the organic solvent is chosen from alcohol of C1 to C4, tetrahydrofuran and ethyl acetate; the catalyst is chosen from palladium carbon and Raney nickel.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a preparation method of a sartan side chain compound, an important intermediate of sartan antihypertensive drugs. Background technique [0002] The compound of structural formula II is a sartan side chain compound which is an important intermediate for preparing sartan antihypertensive drugs. Usually, the compound of structural formula II is obtained by bromination of the compound of structural formula I. Commonly used brominating reagents include bromine, NBS, dibromohydantoin, etc., and representative patents include EP470794, EP0470795, US5310928, EP1777224, and WO2006067215. [0003] [0004] No matter which bromination reagent is used, there is the problem of excessive bromination, and a certain amount of dibrominated compounds (compounds of structural formula III) will exist in the product. When we obtain the target product by crystallization, the crystallization mother...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D257/04
Inventor 闫起强
Owner CHINA RESOURCES SAIKE PHARMA