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A kind of synthetic method of allopurinol impurity c

A synthetic method and compound technology, applied in organic chemistry and other fields

Inactive Publication Date: 2016-03-02
HYBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, there is no report of directly synthesizing allopurinol impurity C in the existing technology, therefore, it is of great practical significance to provide a synthetic method of allopurinol impurity C for the preparation of impurity standards

Method used

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  • A kind of synthetic method of allopurinol impurity c
  • A kind of synthetic method of allopurinol impurity c
  • A kind of synthetic method of allopurinol impurity c

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1 Preparation of compound shown in formula I

[0042] Drop into 3-aminopyrazole-4-carboxamide 5.04g (40mmol) in reaction bottle, add solvent xylene 100mL (in g / mL, the mass volume ratio of 3-aminopyrazole-4-carboxamide and xylene is 1:19.8), stirred, heated to 80°C to dissolve, put in 3.52g (40mmol) of dicarboxylhydrazide, heated to 145°C and refluxed for 5 hours, cooled to room temperature, poured out xylene, added 300mL petroleum ether, at 60 Stir overnight under the condition of ℃~90℃. Suction filtration, the filter cake was washed 3 times with acetone, and lyophilized to obtain 5.45 g of solid, with a yield of 76.5%, and an HPLC purity of 98.18%. The HPLC spectrum is as follows: figure 1 As shown, the HPLC spectrum data are shown in Table 1. Mass spectrum such as figure 2 As shown, the mass spectrometry results showed MS: 179.07 (M+1). The H NMR spectrum is as image 3 As shown, the proton NMR spectrum data are: 1 HNMR(400MHz,DMSO)δ8.90(s,10H),8.41...

Embodiment 2

[0047] Embodiment 2 Preparation of compound shown in formula I

[0048] Add 126.12g (1mol) of 3-aminopyrazole-4-carboxamide in the reaction kettle, add solvent xylene 2.5L (in g / mL, the mass volume ratio of 3-aminopyrazole-4-carboxamide and xylene 1:19.8), stirred, heated to 80°C to dissolve, put in 88.1g (1mol) of diformylhydrazide, heated to 145°C and refluxed for 7 hours, cooled to room temperature, poured out xylene, added 7.5L petroleum ether, Stir overnight at 60°C to 90°C. After centrifugation, the solid was washed 3 times with acetone and freeze-dried to obtain 139.5 g of solid with a yield of 78.3%, an HPLC purity of 98.15%, and MS: 179.09 (M+1). The results showed that the solid obtained after lyophilization was allopurinol impurity C, and its structural formula was shown in Formula I.

[0049]

Embodiment 3

[0050] Embodiment 3 Preparation of compound shown in formula I

[0051] 126.12g (1mol) of 3-aminopyrazole-4-carboxamide was dropped into the reaction kettle, and 3.0L of solvent xylene was added (in g / mL, the mass volume ratio of 3-aminopyrazole-4-carboxamide to xylene 1:23.8), stirred, heated to 80°C to dissolve, put in 105.72g (1.2mol) of diformylhydrazide, heated to 145°C and refluxed for 6 hours, cooled to room temperature, poured out xylene, added 350mL petroleum ether, Stir overnight at 60°C to 90°C. After suction filtration, the filter cake was washed 3 times with acetone, prepared and freeze-dried to obtain 141.1 g of solid, with a yield of 79.2%, an HPLC purity of 98.10%, and MS: 179.07 (M+1). The results showed that the solid obtained after lyophilization was allopurinol impurity C, and its structural formula was shown in Formula I.

[0052]

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Abstract

The invention relates to the field of compound synthesis and particularly relates to a synthesis method of an allopurinol impurity C. The method comprises the following steps: performing a cyclization reaction on 3-aminopyrazole-4-formamide as shown in a formula II and dimethylformamide in the presence of an organic solvent, and refining to obtain the allopurinol impurity C. The synthesis method is simple, mild in reaction conditions and prone to purity, and the product is easy to obtain.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for synthesizing allopurinol impurity C. Background technique [0002] Gout is a disease in which urate crystals precipitate in joints, soft tissues, cartilage and kidneys due to purine metabolism disorders and / or uric acid excretion disorders, causing lesions in human organs and tissues. Gout can lead to serious complications, including gouty arthritis, gouty nephropathy, gouty kidney stones, gouty heart disease, gouty hypertension, etc. Patients have symptoms such as joint pain, renal colic, or hematuria. With the improvement of people's living standards and changes in eating habits, the incidence of gout in my country has been increasing year by year in recent years. [0003] Allopurinol is a commonly used drug for the treatment of gout. The chemical name of allopurinol is 1H-pyrazolo[3,4-d]pyrimidin-4ol, and the molecular formula is C 5 h 4 N 4 O, the molecular...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 袁慧星李国弢刘建马亚平袁建成
Owner HYBIO PHARMA