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Preparation method of dapagliflozin impurity

A technology of impurities and compounds, applied in the field of drug synthesis, can solve problems such as unfavorable reactions, easy precipitation of materials, and contamination, and achieve the effects of low preparation cost, stable process, and simple operation

Pending Publication Date: 2022-05-13
JIANGSU WANBANG BIOPHARMLS
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  • Claims
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Problems solved by technology

The self-coupling impurity is one of the impurities that may be produced during the production of dapagliflozin. At present, there is no method for preparing this impurity (compound 2), and the purity and yield of compound 2 are obtained by optimizing the reaction conditions. For example, in the process of preparing compound 4, temperature has a greater impact on the reaction yield. If the temperature is too high, the reaction becomes impurity, and if the temperature is too low, the material is easy to separate out and is not conducive to the reaction; , the reaction yield is higher

Method used

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  • Preparation method of dapagliflozin impurity
  • Preparation method of dapagliflozin impurity
  • Preparation method of dapagliflozin impurity

Examples

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Embodiment 1

[0034] To a dry 250mL three-necked flask, add 80mL of tetrahydrofuran (8mL / g), start stirring, and then add 5-bromo-2-chloro-4'-ethoxydiphenylmethane (Compound 3) (10.0g, 30.7mmol, 1.0eq). After nitrogen displacement protection, the temperature was lowered to -80~-70°C. After the internal temperature of the system drops to -80~-70°C, add (2.5mol / L) n-BuLi solution 13.5mL (1.1eq) dropwise to react, and the temperature is controlled between -80~-70°C during the dropping process. After the dropwise addition was completed, the reaction was continued within the temperature range for 1.5 h to obtain solution A.

[0035] Add methyl pinacol borate (11.7g, 46.1mmol, 1.5eq) into another 250mL three-necked flask and dissolve it in 50mL of tetrahydrofuran to prepare solution B, start stirring, and add the above-prepared solution A to solution B dropwise , During the dropping process, the temperature is controlled between -80 and -70°C, and the reaction is continued within this temperatu...

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Abstract

The invention discloses a preparation method of a dapagliflozin impurity, n-butyllithium is dropwise added into a 5-bromo-2-chloro-4 '-ethyoxyl diphenylmethane solution to prepare a lithium reagent, the lithium reagent reacts with pinacol methyl borate, and the dapagliflozin impurity is prepared through Suzuki coupling reaction, reactants used in the method are common, the process is stable, and the total yield of the two-step reaction is 53%.

Description

technical field [0001] The invention relates to a preparation method of dapagliflozin impurities, belonging to the technical field of drug synthesis. Background technique [0002] (1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol, and (2S)-1, The hydrate of 2-propanediol (1:1:1), the structure of compound 1 is: [0003] [0004] Dapagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes. It is a new type of anti-diabetic drug jointly developed by Bristol-Myers Squibb and AstraZeneca, and it is a sodium-glucose-dependent transporter SGLT2 inhibitor. The mechanism of action of Dapagliflozin is to reduce the renal glucose reabsorption and increase the excretion of glucose in the urine by inhibiting the expression of transporter 2 (SGLT2) in the kidney, thereby reducing the plasma glucose level. [0005] At present, in the disclosed method of synthesizing dapagliflozin, most of them adopt 5-bromo-2-chl...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/225
CPCC07F5/025C07C41/30C07C43/225
Inventor 张海峰朱信猛李春雷王克艳
Owner JIANGSU WANBANG BIOPHARMLS
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