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Industrial production method of 4-amino-5-imidazolecarboxamide

A technology of imidazole carboxamide and production method is applied in the field of industrialized production of 4-amino-5-imidazole carboxamide, and can solve the problem that 4-amino-5-imidazole carboxamide cannot meet industrialized production, cannot generate economic benefits, and has no large-scale production. Scale supply and other issues, to achieve the effect of low price, stable quality and environmental friendliness

Inactive Publication Date: 2020-07-03
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Except above-mentioned two kinds of main synthetic methods reported in literature, also have the report of some other synthetic methods {Tetrahedron Letters, 25 (49), 5701-5704, 1984; Canadian Journal of Chemistry, 59 (9), 1347-1356, 1981; Agricultural and Biological Chemistry, 41(12), 2331-2334, 1977; Journal of the American Chemical Society, 82, 3144-3146, 1960; Journal of Organic Chemistry, 24, 256-257, 1959; Journal of Biological Chemistry, 181, 89-93,1949}, but these methods all need to be synthesized from very complex intermediate raw materials, and most of the above-mentioned complex intermediate raw materials are hardly supplied on a large scale, and these complex intermediate raw materials are expensive. Generally very high, resulting in the synthesis of 4-amino-5-imidazole carboxamide, which cannot produce economic benefits
[0008] In summary, the synthetic methods of existing 4-amino-5-imidazole carboxamides cannot meet the needs of suitability for industrialized production

Method used

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  • Industrial production method of 4-amino-5-imidazolecarboxamide

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Embodiment 1

[0041] A kind of industrialized production method of 4-amino-5-imidazole carboxamide, specifically comprises the following steps:

[0042] Step 1, synthesis of intermediate 1:

[0043] Under the protection of argon, add THF 1620mL, diaminomaleonitrile 324g, formamide 162g (1.2eq.) to a 5L three-necked flask equipped with a thermometer, dropping funnel and mechanical stirring, and cool down to 5°C in a cryogenic bath , began to add 550.8g (1.2eq.) of phosphorus oxychloride dropwise, and kept warm at 5°C for 2 hours after dropping, and began to take samples every 1 hour. When diaminomaleonitrile LC<0.3%, stop the reaction.

[0044] Post-treatment: Control the temperature at 20°C, add methanol 345.6g dropwise to the reaction solution, after the dropwise addition, control the temperature at 20°C for 2 hours, then slowly pour the system into 4.2L of water to quench, after quenching, keep warm at 20°C and stir for 20min , add 795g of sodium carbonate powder in batches until the pH of...

Embodiment 2

[0050] A kind of industrialized production method of 4-amino-5-imidazole carboxamide, comprises the following steps:

[0051] Step 1, synthesis of intermediate 1:

[0052] Under the protection of argon, add THF 1458mL, diaminomaleonitrile 162g, formamide 101.3g (1.5eq.) successively to a 5L three-neck flask equipped with a thermometer, a dropping funnel and a mechanical stirrer, and the low temperature bath is cooled to 0 ℃, start dropwise adding 344.7g (1.5eq.) of phosphorus oxychloride, keep warm at 35℃ for 2h after dropping, start sampling every 1h, stop the reaction when LC<0.3% of diaminomaleonitrile.

[0053] Post-treatment: Control the temperature at 30°C, add methanol 216g dropwise to the reaction liquid, after the dropwise addition is completed, control the temperature at 30°C for 2 hours, then slowly pour the system into 2.6L of water to quench, after quenching, keep warm at 30°C and stir for 20min, Add 487g of sodium carbonate powder in batches until the system pH=...

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Abstract

The invention discloses an industrial production method of 4-amino-5-imidazolecarboxamide, belonging to the technical field of organic synthesis. The industrial production method comprises the following steps: S1, reacting diaminomaleonitrile with formamide under the action of phosphorus oxychloride to generate an intermediate 1; and S2, subjecting the intermediate 1 to a ring closing reaction under an alkaline condition so as to generate 4-amino-5-imidazolecarboxamide. The method has the advantages of simple raw materials, low price, short reaction steps, short production period, simple operation and easy realization of industrial production, avoids the generation of cyano-containing wastewater, nitrogen-containing wastewater and the like in traditional synthesis methods, causes very small environmental protection pressure, and realizes preparation of the high-quality 4-amino-5-imidazolecarboxamide only through two reactions.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an industrial production method of 4-amino-5-imidazole carboxamide. Background technique [0002] As we all know, Temozolomide (TMZ) is a drug for the treatment of glioma. Compared with other types of anti-tumor drugs, this drug has many unique advantages: such as a broad anti-tumor spectrum, can be taken orally and It has a good absorption effect, is easy to pass through the brain-blood barrier, has good tolerance, has little bone marrow suppression, and does not produce superimposed toxicity when taken together with other drugs, and has good safety. What is even more miraculous is that temozolomide not only has a good curative effect on glioma, but also has a good therapeutic effect on lymphoma, solid tumor, leukemia and melanoma {new oral anti-tumor drug-temozolomide[J]. Oncology: Foreign Volumes, 1999,26(1):292-293.}. Temozolomide drug was firstly deve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 何汉江曹恒明王磊王小伟何京
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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