A New Process for the Preparation of 4-Pyridine Butanol

A technology of pyridine butanol and new process, applied in the direction of organic chemistry, etc., can solve problems such as instability, difficult storage, rising cost, etc., and achieve the effects of good stability, easy purification, and convenient storage

Inactive Publication Date: 2011-11-30
WISDOM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Unfortunately, we found that the intermediate 4-(4-pyridyl)-3-butyn-1-ol of this route is very unstable, difficult to store, and very difficult to separate and purify (due to the instability of the compound, degradation occurs during the purification process) ; If it is d

Method used

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  • A New Process for the Preparation of 4-Pyridine Butanol
  • A New Process for the Preparation of 4-Pyridine Butanol
  • A New Process for the Preparation of 4-Pyridine Butanol

Examples

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Embodiment

[0026] 1. Preparation of 4-(4-pyridyl)-3-butyn-1-alcohol hydrochloride

[0027] Add 4-bromopyridine hydrochloride (45.0 g), triethylamine (450 mL), and deionized water (90 mL) into the reaction flask in sequence, and stir to dissolve. Lithium chloride (0.5g), cuprous iodide (0.5g) and 3-butyn-1-ol (19.5g) were added, and the reaction mixture was stirred for 0.5h, and tetrakis(triphenylphosphine)palladium (0.1g ), back flow reaction 3h. Cool down to room temperature, separate the organic layer, extract the aqueous layer with an organic solvent, combine the organic layers, and distill off the solvent under reduced pressure to obtain a light brown oily liquid (34.5g). The resulting oil was directly dissolved in ether (200mL), and 6mol.L was added dropwise under ice-cooling -1 Hydrogen chloride ethanol solution (43mL), stirred in ice bath for 2h. Filter and dry to obtain a white powdery solid (36.4g). TLC detected no impurities (R f =0.6, developer: ethyl acetate, sample pre-...

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Abstract

The invention relates to a new preparation process of tirofiban hydrochloride key intermediate 4-pyridine butanol. The key to the process is to make the reaction intermediate 4-(4-pyridyl)-3-butyn-1-ol into hydrochloride or sulfate to improve its stability, and the corresponding salt can be hydrogenated under normal temperature and pressure to obtain the corresponding Pyridine butanol hydrochloride or sulfate, the latter can prepare high-purity 4-pyridine butanol by distillation under reduced pressure after freeing triethylamine. This route does not involve expensive reagents, has low requirements for equipment, is simple to operate, and is highly feasible for industrial scale-up.

Description

technical field [0001] The invention relates to a new preparation process of tirofiban hydrochloride key intermediate 4-pyridine butanol. [0002] Background technique [0003] Tirofiban hydrochloride (N-n-butylsulfonyl-O-4-(4-piperidinyl)butyl)-L-tyrosine hydrochloride monohydrate,) as a reversible non-peptide The platelet GPIIb / IIa receptor antagonist was developed by Merck, an international pharmaceutical giant, in the 1990s, and was successfully approved by the US FDA in May 1998. At present, the platelet antagonist has been sold in Switzerland, China, Germany and the Netherlands It is widely used in other countries. The drug is suitable for patients with unstable angina or non-Q wave myocardial infarction to prevent cardiac ischemic events. Cardiac ischemic complications associated with sudden occlusion of treated coronary arteries. The structural formula of tirofiban hydrochloride is as follows: [0004] [0005] So far, chemists have developed many synthetic r...

Claims

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Application Information

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IPC IPC(8): C07D213/30
Inventor 邱小龙李冰健李宏名邹平张义森刘时奎葛亮杨登贵
Owner WISDOM PHARM CO LTD
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