Synthesis process for anti-tumor new medicine 3-{(3-chlorphenyl)difluoromethyl-1-isopropyl-monohydro-pyrazolo(3,4-D)pyrimidine-4-amine compound

A difluoromethyl and chlorophenyl technology, applied in the field of medicine, can solve problems such as unsatisfactory treatment, unresponsiveness or drug resistance of cancer patients, and treatment failure

Inactive Publication Date: 2012-04-04
CGENETECH (SUZHOU CHINA) CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0002] Nearly 50 years of research and development of anti-tumor drugs have made considerable progress in cancer chemotherapy, especially prolonging the survival time of patients with hematological malignancies, but the treatment of solid tumors, which seriously threaten human life and health and account for more than 90% of malignant tumors

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  • Synthesis process for anti-tumor new medicine 3-{(3-chlorphenyl)difluoromethyl-1-isopropyl-monohydro-pyrazolo(3,4-D)pyrimidine-4-amine compound
  • Synthesis process for anti-tumor new medicine 3-{(3-chlorphenyl)difluoromethyl-1-isopropyl-monohydro-pyrazolo(3,4-D)pyrimidine-4-amine compound

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specific Embodiment approach

[0023] Preparation of 2-(3-chlorophenyl)-2,2-difluoroacetyl chloride:

[0024] 206.6 g (1 mole) of starting material 2-(3-chlorophenyl)-2,2-difluoroacetic acid was dissolved in 2 liters of dichloromethane, and 254 g (2 moles) of oxalyl chloride was added dropwise after adding 5 ml of DMF Under ice-water cooling, the solution was raised to room temperature and stirred for 3 hours, and spin-dried to obtain 225 g of acid chloride (yield 100%), which was directly used in the next step without purification.

[0025] Docking with acrylonitrile:

[0026] Dissolve 66 grams (1 mole) of malononitrile in 680 milliliters of DMF, cool to 0°C, add 44 grams (1.1 moles) of sodium hydrogen (60% purity) in batches, react at room temperature for 1 hour after the addition, and cool in an ice-salt bath Add dropwise the acid chloride obtained in the step, control the temperature below 5 degrees, and react overnight at room temperature after completion. TLC detects that the reaction is complete. (...

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Abstract

The invention discloses a synthesis method for an anti-tumor new medicine 3-{(3-chlorphenyl)difluoromethyl-1-isopropyl-monohydro-pyrazolo(3,4-D)pyrimidine-4-amine compound. The synthesis method comprises the following steps of: acylating 3-chlorphenyl-2 oxalic acid serving as an initiative raw material; reacting the acylated material with dipropionitrile; performing methylation; performing ring closure with hydrazine hydrate to obtain 5-amino-1-(3-chlorophenyl)-pyrazole-4-carbonitrile, crystallizing and purifying, heating and performing ring closure with formamide to obtain a target mother ring; performing fluorination on carbonyl by using DAST; introducing difluorine into an active group so as to improve the bioactivity of the compound; performing process optimization on the basis of the compound; and performing the similar steps by using 2-(3-chlorphenyl)-2,2-difluoroacetic acid as a raw material to obtain the target product.

Description

technical field [0001] The present invention relates to the design and application of new antitumor drug 3-{(3-chlorophenyl)difluoromethyl-1-isopropyl-1hydro-pyrazolo(3,4-D)pyrimidine-4-amine compounds The synthesis belongs to the field of medicine and chemical technology. Background technique [0002] Nearly 50 years of research and development of anti-tumor drugs have made considerable progress in cancer chemotherapy, especially prolonging the survival time of patients with hematological malignancies, but the treatment of solid tumors, which seriously threaten human life and health and account for more than 90% of malignant tumors, has not yet been developed. Even if a satisfactory curative effect is achieved, half of the cancer patients still have no response or drug resistance to treatment, which eventually leads to treatment failure. Therefore, discovering and developing new antitumor drugs is still a very arduous and long-term mission and challenge that pharmacists mu...

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
Inventor 张福治张仁延丁炬平余强
Owner CGENETECH (SUZHOU CHINA) CO LTD
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