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Synthetic method of procarbazine

A synthetic method, the technology of procarbazine, applied in the field of drug synthesis, can solve the problems of production equipment and unfriendly environment, and achieve the effect of high yield

Inactive Publication Date: 2019-08-23
广州药本君安医药科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Pcb synthesis method reported in the literature includes 4 steps, also using p-toluic acid as the starting material, the total yield is 46.7%, but in step iii) strong acid and strong oxidant are used, which is not friendly to production equipment and the environment

Method used

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  • Synthetic method of procarbazine

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Embodiment

[0033] The synthetic method of procarbazine comprises the following steps:

[0034] a), the preparation of p-toluamide

[0035] Weigh 240.2mg (2.0mmol) of p-tolualdehyde in a 25mL round-bottomed flask, add 5.0mL of dry methylene chloride, weigh 343.2mg (1.2mmol) of dibromoisocyanuric acid and add it to the system. React at room temperature for 4 hours, weigh 303.3mg (3mmol) of triethylamine and 178.2mg (3mmol) of isopropylamine and dissolve them in 2ml of dichloromethane, slowly add them to the reaction system, then react for 10min, TLC plate detection, wait until the reaction is complete , adding 50ml of water, extracted three times with 50ml of dichloromethane, combined the organic phases, washed twice with water, dried over anhydrous sodium sulfate, and spin-dried the organic solvent to obtain a colorless oily liquid. Silica gel column chromatography (ethyl acetate-petroleum ether, volume ratio 3:1) gave 303.1 mg of white solid compound N-isopropyl-p-toluamide with a yield...

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Abstract

The invention discloses a synthetic method of procarbazine (Pcb). The synthetic method comprises following steps: p-tolualdehyde is taken as an initial raw material, dibromocyanuric acid and isopropylamine are added, reaction is carried out at room temperature so as to obtain p-methyl benzoyl isopropylamine; p-methyl benzoyl isopropylamine is dissolved in an organic reagent, N-bromo-succinimide and an initiator are added, heating reflux is carried out, after reaction, the solvent is removed, acetonitrile and a hydrolysis promoter are added, heating reflux is carried out so as to obtain p-formyl benzoyl isopropylamine; p-formyl benzoyl isopropylamine and methylhydrazine sulfate are dissolved in an organic reagent, triethylamine is added for reaction, and the solvent is subjected to rotary drying, sodium cyanoborohydride is added, an obtained reaction system is heated to room temperature, reaction is carried out for more than one night so as to obtain Pcb. According to the synthetic method, bromination is carried out firstly, and then hydrolysis is carried out, p-methyl benzoyl isopropylamine is converted into p-formyl benzoyl isopropylamine, using of strong oxidizing agent and strong acid is avoided, the synthetic method is friendly to the environment, the yield is high, and the total yield of the three steps is 52.9%.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and in particular relates to a synthesis method of procarbazine (Pcb). Background technique [0002] Currently, cancer is one of the leading causes of death in both developed and developing countries. In the presence of changes in the ecological environment and lifestyle, population aging, and unhealthy living habits such as smoking and drinking, the number of cancers worldwide and the number of deaths due to cancer will continue to increase. [0003] Procarbazine is mainly used clinically to treat Hodgkin's disease, and it also has a certain effect on other malignant tumors such as malignant lymphoma, lung cancer, and multiple myeloma. [0004] Chinese invention patent ZL 201611118043.5 and literature (Chen, H., et al. Bioorg.Chem.2019, 83, 461-467) both involve the synthesis method of Pcb, among which, the invention patent ZL 201611118043.5 has 6 steps in the synthesis of Pcb, the starting ma...

Claims

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Application Information

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IPC IPC(8): C07C241/02C07C243/18C07C231/10C07C233/65C07C231/12C07C235/84
CPCC07C231/10C07C231/12C07C241/02C07C243/18C07C233/65C07C235/84
Inventor 陈河如张潮何业谱林晓洪
Owner 广州药本君安医药科技股份有限公司
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