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Hydrogenated pyridine derivatives and preparation method thereof

A technology for hydrogenating pyridine and derivatives, applied in the direction of organic chemistry, etc., to achieve the effect of speeding up the reaction, reducing the generation of by-products, and mild preparation conditions

Active Publication Date: 2016-01-20
CHENGDU BAIYU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no relevant documents and patents reporting the preparation method of the above-mentioned impurities (especially high-purity above-mentioned impurities)

Method used

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  • Hydrogenated pyridine derivatives and preparation method thereof
  • Hydrogenated pyridine derivatives and preparation method thereof
  • Hydrogenated pyridine derivatives and preparation method thereof

Examples

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Effect test

Embodiment 1

[0042] Compound 2: Preparation of 2-phenyl-1-cyclopropylethanone

[0043] in N 2 Under protection, add about 1-2ml of benzyl chloride (38g, 0.3mol) diluted with 114ml of tetrahydrofuran dropwise into a reaction flask containing 114ml of tetrahydrofuran, magnesium powder (8.6g, 0.36mol) and a few grains of iodine, and heat the reaction slightly. System, after the reaction is initiated and the brown color fades, slowly add the remaining benzyl bromide-tetrahydrofuran solution dropwise under temperature control at 25-30°C. Add dropwise to 114ml tetrahydrofuran diluted cyclopropylnitrile (24.1g, 0.36mol) at ~10°C. After the dropwise addition, keep the reaction at room temperature for 8 hours, stop the reaction, add 200ml ether to the reaction system, and then 25~ Add 100ml of water dropwise to the reaction solution at 30°C, then adjust the pH of the system to <4 with 2N hydrochloric acid at 25-30°C, separate the water phase, wash the organic phase with 150ml of 5% sodium bicarbon...

Embodiment 2

[0045] Compound 2: Preparation of 2-phenyl-1-cyclopropylethanone

[0046] in N 2Under protection, add about 1-2ml of benzyl bromide (30g, 0.17mol) diluted with 150ml of ether to the reaction flask with 150ml of ether, magnesium powder (6.3g, 0.26mol) and a few grains of iodine, and heat the reaction slightly. System, after the reaction is initiated and the brown color subsides, slowly add the remaining benzyl bromide-ether solution dropwise at a temperature of 15-20°C. After the dropwise addition, keep stirring at 15-20°C for 1 hour, and then add the Grignard reagent obtained above to - Add dropwise to 150ml of cyclopropylnitrile (17.6g, 0.26mol) diluted with ether at 5-0°C. After the dropwise addition, keep the reaction at room temperature for 8 hours, stop the reaction, and drop into the reaction solution at 25-30°C Add 100ml of water, adjust the pH of the system to <4 with 2N hydrochloric acid at 25-30°C, remove the aqueous phase, wash the organic phase with 120ml of 5% so...

Embodiment 3

[0048] Compound 3: Preparation of 2-phenyl-2-bromo-1-cyclopropylethanone

[0049] Add 2-phenyl-1-cyclopropylethanone (39.3g, 0.25mol), PTSA (3.9g), 120ml methanol, NBS (48.0g, 0.27mol) to the reaction flask, and react at 40-45°C for 5 hour, after stopping the reaction, add 120ml ethyl acetate and 120ml5% sodium bicarbonate solution to the reaction system, separate the water phase, and then wash the organic phase with 120ml water, evaporate the solvent to obtain 54g yellow liquid, yield 91.6% , HPLC: 94.2%.

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Abstract

The invention discloses a hydrogenated pyridine derivative shown by a formula I and a preparation method thereof, wherein R1 is H or F, R2 is H or F, and the R1 and R2 are not F at the same time. According to the preparation method, process parameters are optimized, the biological purity of the prepared hydrogenated pyridine derivative is more than 99%, the preparation condition is mild, and starting materials are easily available.

Description

technical field [0001] The invention relates to a hydrogenated pyridine derivative and a preparation method thereof. Background technique [0002] Prasugrel is a new generation antithrombotic drug jointly developed by Daiichi Pharmaceutical Sankyo Co., Ltd. and Eli Lilly and Company of the United States, and its trade name is Effient. The drug was approved by the European Commission in February 2009 for the prophylaxis of atherothrombotic events in patients with acute coronary syndrome who have undergone emergency and delayed percutaneous coronary intervention. This is the first time that prasugrel has been approved worldwide, and it was launched in the UK and Germany on April 8, 2009. In August 2009, it was approved by the US FDA and launched in the US for the treatment of thromboembolism and coronary artery disease. The chemical name of prasugrel is 2-acetoxy-5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine, As shown in formula V. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 周勇施智锋李善伟孙毅
Owner CHENGDU BAIYU PHARMA CO LTD
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