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Method for purifying sartan side chain compound

A purification method and compound technology, applied in the direction of carboxylic acid nitrile purification/separation, organic chemistry, etc., to achieve the effect of easy recovery and little impact on product stability

Active Publication Date: 2013-05-08
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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There is still no relevant literature or patent in China

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  • Method for purifying sartan side chain compound
  • Method for purifying sartan side chain compound
  • Method for purifying sartan side chain compound

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: Synthesis of 4'-bromomethyl-2-cyanobiphenyl crude product

[0022] In a 2L three-necked flask, add 96.6g (0.50mol) 4'-methyl-2-cyanobiphenyl (OTBN), 94g bromosuccinimide, 600ml dichloromethane, 2.0g benzoyl peroxide , heated to reflux for 10h, then cooled to room temperature, and filtered, the dichloromethane layer was washed with 400ml of 5% sodium bicarbonate, washed with water, concentrated and evaporated to dryness, and then processed to obtain 136g of 4'-bromomethyl-2-cyanobiphenyl . (HPLC result: Br-OTBN 84.6%, Br 2 -OTBN9.0%, OTBN 6.0%)

Embodiment 2

[0023] Embodiment 2: Purification of 4'-bromomethyl-2-cyanobiphenyl

[0024] The above solid was suspended in 200ml methyl ethyl ketone, heated to 50-55°C, then kept for 2 hours, then gradually cooled to 10-15°C, kept for crystallization for 4 hours, filtered, and 108.8g was obtained after the solid was dried, with a total yield of 80%. Solid purity greater than 98%.

[0025] The above method is used for secondary purification, the purity is greater than 99%, and the secondary purification yield is greater than 93%.

Embodiment 3

[0026] Embodiment 3: Synthesis of crude product of N-(triphenylmethyl)-5-(4'-bromomethylbiphenyl 2-yl)tetrazolium

[0027] In a 500ml three-necked flask, add 47.8g (0.10mol) N-(triphenylmethyl)-5-(4'-methylbiphenyl-2-yl)tetrazolium, 200ml dichloromethane, 19g bromo Succinimide, 1g benzoyl peroxide, warming up to reflux for 5-6 hours, then cooling to room temperature, filtering, washing the dichloromethane layer with 100ml 5% sodium bicarbonate, washing with water, concentrating and evaporating to dryness, and then processing to obtain 55.0 g of crude N-(triphenylmethyl)-5-(4'-bromomethylbiphenyl-2-yl)tetrazolium. (HPLC results: BBTT 82.3%, Br-BBTT 10.4%, BBTT-Br 6.2%)

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Abstract

The invention relates to a method for purifying sartan side chain compound, especially a method for purifying the compound of formula I, characterized in that, the method comprises the following steps: in the formula I, wherein, B represents the following structure: (Fig), suspending the solid crude product obtained by the compound of formula I through the bromination reaction in the appropriate organic solvent; stirring and washing for heat preserving; and then cooling to crystallize.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a purification method of a sartan side chain compound, an important intermediate of sartan antihypertensive drugs. Background technique [0002] The compound of structural formula I (4'-bromomethyl-2-substituted biphenyl compound) is an important intermediate for the preparation of sartan antihypertensive drugs, which was first reported in EP0253310. Usually, the compound of structural formula I is obtained by bromination of the compound of structural formula II. Commonly used brominating reagents include elemental bromine, elemental bromine / oxidant, bromosuccinimide, dibromohydantoin, etc., and representative patents include EP470794, EP0470795 , US5621134, US2003 / 0233009, EP553879, US6177587, US2002 / 0095042. [0003] [0004] No matter which kind of brominating agent is adopted, there is the problem of excessive bromination, and there will be a certain amount of dibromo comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/34C07D257/04
Inventor 刘沫毅李志强胡尧尧王文峰
Owner CHINA RESOURCES SAIKE PHARMA
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