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Preparation method of novel tadalafil derivative

A derivative and non-new technology, which is applied in the field of preparation of new derivatives of tadalafil, can solve the problems of high risk factor and complicated process, and achieves the effects of low operation risk factor, short and simple reaction steps and high purity

Pending Publication Date: 2022-05-06
广西东盟食品检验检测中心
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Problems solved by technology

[0003] The invention provides a preparation method of a novel derivative of tadalafil to solve the problems of cumbersome process and high risk factor in the prior art

Method used

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  • Preparation method of novel tadalafil derivative
  • Preparation method of novel tadalafil derivative
  • Preparation method of novel tadalafil derivative

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Experimental program
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Embodiment 1

[0037] The overall synthetic route of tadalafil novel derivatives is as follows: figure 1 Shown, the following is the specific preparation process.

[0038] (1) Synthesis of Compound 2

[0039] Weighed 1350.12 mg (1 mmol) of compound 1350.12 mg (1 mmol) into a 100 mL pear-shaped reaction flask, added 10 mL of dichloromethane and stirred at room temperature until compound 1 was dissolved, then lowered the temperature to 0°C, added 0.108 mL of chloroacetyl chloride, and then added 0.361 mL of Tris Ethylamine, stirred and reacted at room temperature for 6h, followed the reaction by TLC, and stopped the reaction when no obvious raw materials were found. The reaction solution was washed with water, extracted with dichloromethane, washed with saturated sodium chloride solution, and extracted three times in sequence. The organic phases were combined, and the solvent was removed under reduced pressure to obtain a solid crude product, which was separated by column chromatography to ob...

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Abstract

The invention provides a synthesis method of a tadalafil novel derivative, which comprises the following steps: (1) taking a cis-tetrahydrocarboline compound as an initial raw material, and carrying out chloroacetylation reaction on the cis-tetrahydrocarboline compound, chloroacetyl chloride and triethylamine to obtain an acetylated product; and (2) carrying out cycloaddition reaction on chloroacetyl chloride groups of the acetylation product under the action of triethylamine under an alkaline condition, and carrying out ring shrinkage reaction on the chloroacetyl chloride groups and cyclohexylamine to prepare the novel tadalafil derivative. The impurity (a novel tadalafil derivative) is synthesized for the first time, meanwhile, the provided process for synthesizing the impurity has the advantages of being short in reaction step, few in by-products, good in yield (larger than 80%), high in purity (HPLC 100%) and the like, and the method has important significance on quality control of tadalafil raw material medicine.

Description

【Technical field】 [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of a novel tadalafil derivative. 【Background technique】 [0002] Tadalafil is a selective reversible phosphodiesterase 5 (PDE5) inhibitor, a prescription drug for the treatment of male erectile dysfunction, which must be taken under the guidance of a doctor. At present, tadalafil derivatives basically use piperonal as the starting material, and are prepared through a series of reactions. They are widely used because of their simple reaction and low toxicity. "Regulations" and "Regulations on the Administration of Precursor Chemicals" usually require cumbersome treatments such as column chromatography separation or recrystallization to obtain high-purity cis-carboline intermediates, which have problems such as cumbersome processes and high risk factors . 【Content of invention】 [0003] The invention provides a preparation method of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14
CPCC07D471/14
Inventor 刘珈伶杨方方戴向东苏俞有曾令阳陈小聪覃文霞王警韦环
Owner 广西东盟食品检验检测中心
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