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Varenicline tartrate intermediate impurity and preparation method thereof

A technology for varenicline tartrate and its intermediates, which is applied in organic chemistry and other fields, can solve the problem of no impurity I preparation method, etc., and achieve the effect of improving the identification and separation of impurities and improving product quality

Pending Publication Date: 2022-07-01
JIANGSU SINOBIOPHARMA
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Problems solved by technology

[0007] At present, there is no relevant literature report on the preparation method of impurity Ⅰ

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  • Varenicline tartrate intermediate impurity and preparation method thereof
  • Varenicline tartrate intermediate impurity and preparation method thereof
  • Varenicline tartrate intermediate impurity and preparation method thereof

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Embodiment Construction

[0025] The technical solutions of the present invention are further described below with reference to the accompanying drawings. The embodiments and related experimental data described below with reference to the accompanying drawings are only exemplary, and are intended to be used to explain the present invention, but should not be construed as a limitation of the present invention.

[0026] 1. Preparation of Intermediate 1

[0027] Add 250ml of dichloromethane and 25g of starting materials to the reaction flask, turn on stirring, cool down to 0~5°C, add 31.0g of triethylamine in the system, and add 32.2g of trifluoroacetic anhydride dropwise to the system at 0~5°C After dropping, the temperature was raised to 20-30°C, and the reaction was stirred for 2 h. 250 ml of water was added to the reaction solution, stirred for 1 h, allowed to stand, layered, and the organic phase was collected. The aqueous phase was extracted with 250 ml of dichloromethane, and the organic phases wer...

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Abstract

The preparation method comprises the following steps: reacting an initial raw material with trifluoroacetic anhydride in dichloromethane under the catalysis of triethylamine to obtain an intermediate 1, carrying out nitration reaction on the intermediate 1 and fuming nitric acid under the catalysis of concentrated sulfuric acid, extracting and concentrating dichloromethane to obtain an intermediate 2, and purifying the intermediate 2 to obtain the varenicline tartrate intermediate impurity. Carrying out reduction reaction on the intermediate 2 under the catalysis of palladium carbon to obtain an intermediate 3; and carrying out cyclization reaction on the intermediate 3 and triethyl orthoformate under the catalysis of sulfamic acid to obtain the varenicline tartrate intermediate impurity. The preparation method of the impurity is provided for the first time and can be better applied to the existing preparation process of the varenicline tartrate key intermediate, the impurity identification and separation degree is improved, and the product quality is improved.

Description

technical field [0001] The invention relates to an intermediate impurity of varenicline tartrate and a preparation method thereof, belonging to the technical field of pharmaceutical synthesis. Background technique [0002] Varenicline tartrate is a partial agonist that selectively acts on α4β2 nicotine receptors, and is mainly used clinically as a drug for smoking cessation in adults. Varenicline selectively binds to the α4β2 nicotine acetylcholine receptor with high affinity. Varenicline binds to the α4β2 nicotine acetylcholine receptor subtype to produce an agonistic effect, while blocking the binding of nicotine to this receptor, which is the mechanism by which varenicline exerts its smoking cessation effect. [0003] The published synthetic methods of varenicline tartrate are basically the same, all of which are based on 2,3,4,5-tetrahydro-1,5-methylene-1H-3-benzazepine As a starting material, the amino group is first protected with a trifluoroacetyl group, and then a...

Claims

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Application Information

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IPC IPC(8): C07D471/08
CPCC07D471/08
Inventor 黄乐群汪静王磊
Owner JIANGSU SINOBIOPHARMA
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