Synthesis process of Tilofiban hydrochloride intermediate

A technology for tirofiban and intermediates, which is applied in the field of key intermediates for the preparation of tirofiban hydrochloride, which can solve the difficulties in industrial preparation, storage and transportation of butyllithium, and the difficulty in industrial production of tirofiban hydrochloride, hydrochloric acid Eliminate the high cost of tirofiban, and achieve the effects of good yield and quality, easy operation, and avoiding low-temperature reactions

Active Publication Date: 2006-03-01
LUNAN PHARMA GROUP CORPORATION
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  • Abstract
  • Description
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Problems solved by technology

Due to the reaction at an extremely low temperature and the need for anhydrous and oxygen-free tetrahydrofuran solvents, the above conditions make it difficult to realize industrial production of tirofiban hydrochloride; Higher non-class costs

Method used

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  • Synthesis process of Tilofiban hydrochloride intermediate
  • Synthesis process of Tilofiban hydrochloride intermediate

Examples

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Embodiment Construction

[0009] The preparation method of the present invention is further described in detail below by way of examples.

[0010] 1. Preparation of 4-(4-pyridyl)butyl chloride:

[0011] In a 5L three-neck bottle, pass dry nitrogen protection, add 1.6L of anhydrous ether, 1250ml of diisopropylamine, 50g of lithium metal, and add dropwise a solution of 460ml of styrene and 300ml of anhydrous ether in a water bath heated to reflux , after the addition, reflux and stir for 2 hours, the lithium flakes completely disappeared, and a gray solution was obtained.

[0012] The reaction solution was cooled with ice water to below 5°C, 465 g of 4-picoline (5 mol, diluted with 300 ml of anhydrous ether) was added dropwise, and the reaction was stirred at room temperature for 2 hours. Cool the reaction solution with ice water to below 5°C, add 820 g (5.2 moles) of 3-bromo-1-chloropropane dropwise, rise to room temperature and stir the reaction, monitor by TLC until the reaction is complete, add 400 ...

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Abstract

The present invention discloses the synthesis process of 4-(4-pyrindyl) butyl chloride as the intermediate of angina pectoris treating medicine Tilofiban hydrochloride.

Description

technical field [0001] The invention relates to a new chemical method for preparing the key intermediate of tirofiban hydrochloride—4-(4-pyridyl)butyl chloride. Background technique [0002] Tirofiban hydrochloride (English name: Tirofiban hydrochloride, chemical name: (S)-N-(n-butylsulfonyl)-O-[4-(4-piperidinyl)butane]-L-tyrosine Hydrochloride monohydrate) is a salt compound of a platelet inhibitor. [0003] European patent application EP478363 discloses a method for synthesizing tirofiban hydrochloride from 4-(4-pyridyl)butyl chloride, and a method for synthesizing 4-(4-pyridyl)butyl chloride from 4-picoline. The method prepares 4-(4-pyridyl)butyl chloride by taking 4-picoline as a raw material to react with butyllithium at -70°C and then reacting with 3-bromo-1-chloropropane for coupling reaction. Due to the reaction at an extremely low temperature and the need for anhydrous and oxygen-free tetrahydrofuran solvents, the above conditions make it difficult to realize indu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26
Inventor 赵志全彭立增
Owner LUNAN PHARMA GROUP CORPORATION
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