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Crystal form of 6, 7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride and preparation method thereof

A chloride, 2-a technology, applied in organic chemistry and other directions, can solve the problems of high equipment requirements, complicated operation, long production cycle, etc., and achieve the effects of high crystal purity, simple operation and low cost

Active Publication Date: 2010-06-16
石药集团中诺药业(石家庄)有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The above-mentioned patents and documents mainly adopt column purification for the preparation of 6,7-dihydro-6-mercapto-5H-pyrazol[1,2-a][1,2,4]triazole ylide chloride, and the operation It is cumbersome, the production cycle is long, and the equipment requirements are high, so it is not suitable for industrial production; and the recrystallization method used is still very immature, and further research is needed

Method used

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  • Crystal form of 6, 7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride and preparation method thereof
  • Crystal form of 6, 7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride and preparation method thereof
  • Crystal form of 6, 7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039]Dissolve 200 g of 6,7-dihydro-6-mercapto-5H-pyrazol[1,2-α][1,2,4]triazolium chloride in 150 mL of methanol, and add 1500 mL of acetone dropwise under stirring, Cool in an ice-water bath, continue to stir until a large amount of solids are precipitated, keep warm for 5 hours, filter with suction, and dry to obtain 165.1 g of white crystals, mp 124-126 °C, HPLC purity 97.6%, conduct powder X-ray diffraction analysis on the obtained crystals, and the results are shown in the table 1, the powder X-ray diffraction spectrum figure of gained crystal sees attached figure 1 .

[0040] Table 1

[0041] d value

Embodiment 2

[0043] Dissolve 200 g of crude 6,7-dihydro-6-mercapto-5H-pyrazol[1,2-α][1,2,4]triazolium chloride in 150 mL of methanol, and then add iso Propanol 900mL, continue to stir until a large amount of solids are precipitated, cool in an ice-water bath, keep warm for 5h, filter with suction, and dry to obtain 155.7g of white crystals. mp 126~128 ℃, HPLC purity 98.0%, carry out powder X-ray diffraction analysis to gained crystal, the result is shown in Table 2, gained crystal powder X-ray diffraction spectrum figure sees attached figure 2 .

[0044] Table 2

[0045] d value

[0046] d value

Embodiment 3

[0048] Dissolve 200g of 6,7-dihydro-6-mercapto-5H-pyrazol[1,2-α][1,2,4]triazolium chloride in 150mL of methanol, and add ethyl acetate dropwise under stirring 250mL, isopropyl ether 250mL, cooled in an ice-water bath, continued to stir until a large amount of solids precipitated, kept warm for 5h, filtered with suction, and dried to obtain 162.4g of white crystals, mp126~128°C, HPLC purity 98.2%, powder X-ray was carried out on the obtained crystals Diffraction analysis, the results are shown in Table 3, and the powder X-ray diffraction spectrum of the gained crystal is shown in the attached image 3 .

[0049] table 3

[0050] d value

[0051] d value

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Abstract

The invention relates to a crystal form of 6, 7-dihydro-6-mercapto-5H-pyrazolo [1,2-alpha][1,2,4] triazoliumchloride and a preparation method thereof. The 6, 7-dihydro-6-mercapto-5H-pyrazolo [1,2-alpha][1,2,4] triazoliumchloride is a key intermediate for synthesizing the carbapenem antibiotic biapenem. The crystal form of 6,7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride is characterized in that the X-ray diffraction spectrum of powder of the crystal form is represented by an angle of 2theta, and has peaks at 27.487+ / -0.2 and 26.707+ / -0.2, the intensity of the peak is 100% when 2theta is 27.487+ / -0.2, and the ratio of intensity of the peak I / I0 is no less than 60% when 2theta is 26.707+ / -0.2. The 6, 7-dihydro-6-mercapto-5H-pyrazolo[1,2-alpha][1,2,4] triazoliumchloride is prepared by the recrystallization method which abandons the column chromatography and has high efficiency and low cost and is more suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a crystal form of 6,7-dihydro-6-mercapto-5H-pyrazol[1,2-a][1,2,4]triazole ylide chloride and its preparation method. Background technique [0002] 6,7-Dihydro-6-mercapto-5H-pyrazol[1,2-a][1,2,4]triazolium chloride is a key intermediate in the synthesis of biapenem, and its structural formula is as follows picture: [0003] [0004] The chemical name of biapenem is 6-[[(4R,5S,6S)-2-carboxy-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-nitrogen Heterobicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-prarazolone[1,2-a][1,2,4]triaza- The 4-inner salt is a 1β-methyl carbapenem antibiotic, and its structural formula is as follows: [0005] [0006] Biapenem was developed by Lederle Corporation of Japan and Cyamide Corporation of the United States, and was jointly listed in Japan by Lederle Corporation of Japan and Meiji Corporation of Japan in March 2002. Biapenem i...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D477/20
Inventor 史颖谢振刚于秀芹李坤谢赞
Owner 石药集团中诺药业(石家庄)有限公司
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