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Pyrazole compound and preparation method thereof

A technology for pyrazoles and compounds, applied in the field of pyrazoles and their preparation, capable of solving problems such as application limitations

Active Publication Date: 2021-08-13
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the process of realizing the present invention, the inventors found that the pyrazole compounds synthesized by the existing synthetic methods are basically substituted pyrazoles, which cannot be used as a good class of synthons, so that their application in drug synthesis is limited

Method used

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  • Pyrazole compound and preparation method thereof
  • Pyrazole compound and preparation method thereof
  • Pyrazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole

[0056]

[0057] Dissolve N-phenylbenzohydrazine chloride (1.0mmol, 1.0eq), prop-2-ynylsulfur salt (2.0mmol, 2.0eq) and potassium carbonate (2.0mmol, 2.0eq) in 10mL of chloroform, nitrogen protection , stirred at 0°C for 24 hours. After the reaction was complete, the reaction system was filtered, and the filtrate was evaporated and concentrated to obtain a residue, which was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 100:1) to obtain a white powder with a yield of 60%.

[0058] White solid, yield 65%. Melting point: 93.8~96.2℃. 1 H-NMR (400MHz, CDCl 3 ):δ7.86(dd, J=7.2,1.6Hz, 2H),7.67-7.63(m,2H),7,54(t,J=7.6Hz,2H)7.47(t,J=7.2Hz, 1H ), 7.42 (t, J = 7.2Hz, 2H), 7.34 (t, J = 7.2Hz, 1H), 6.85 (s, 1H), 4.51 (s, 2H). 13 C NMR (100MHz, CDCl3): δ152.2, 140.3, 139.3, 132.8, 129.6, 128.9, 128.8, 128.4, 126.0, 125.4, 106.2, 21.3; HRMScalcd for C 16 h 13 BrN 2 +H + :313...

Embodiment 2

[0102] Example 2 5-(bromomethyl)-1-phenyl-3-(p-tolyl)-1H-pyrazole

[0103]

[0104] The synthesis procedure is the same as in Example 1, except that N-phenylbenzohydrazine chloride is replaced with (Z)-4-methoxy-N'-phenylbenzohydrazine chloride to obtain a white solid with a yield of 64%.

[0105] White solid, yield 64%. Melting point: 96.5–100.1°C. 1 H-NMR (400MHz, CDCl 3 ): δ7.76 (d, J = 8.0Hz, 2H), 7, 65 (t, J = 6.8Hz, 2H), 7.54 (t, J = 7.6Hz, 2H), 7.46 (t, J = 7.2 Hz ,1H),7.23(d,J=8.0Hz,2H),6.82(s,1H),4.50(s,2H); 13 C NMR (100MHz, CDCl 3 ): δ152.3, 140.2, 139.3, 138.2, 130.0, 129.6, 129.5, 128.7, 125.9, 125.4, 106.0, 21.5, 21.4; HRMS calcdfor C 17h 15 BrN 2 +H + :327.0491,found:327.0488.

Embodiment 3

[0106] Example 3 5-(bromomethyl)-3-(4-methoxyphenyl)-1-phenyl-1H-pyrazole

[0107]

[0108] The synthesis steps are the same as in Example 1, except that N-phenylbenzohydrazine chloride is replaced with (Z)-4-methoxy-N'-phenylbenzohydrazine chloride to obtain a white solid with a yield of 62%.

[0109] White solid, yield 62%. Melting point: 107.8-109.3°C. 1 H-NMR (400MHz, CDCl 3 ):δ 7.81-7.78(m,2H),7.66-7.62(m,2H),7,55-7.51(m,2H),7.47-7.43(m,1H),6.95(d, J=8.8Hz, 2H), 6.77(s,1H), 4.50(s,2H), 3.84(s,3H); 13 C NMR (100MHz, CDCl 3 ): δ159.9, 152.0, 140.20, 139.4, 129.6, 128.7, 127.3, 125.7, 125.4, 114.3, 105.7, 55.5, 21.4; HRMS calcd for C 17 h 15 BrN 2 O+H + :343.0441,found:343.0443.

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Abstract

The invention discloses a pyrazole compound and a preparation method thereof. The structural formula of the pyrazole compound is shown in the specification, wherein R1 is various substituted phenyl groups, naphthyl groups, alkane groups or heterocyclic aryl groups, and R2 is various substituted phenyl groups. The preparation method comprises the following step: performing [3+2] aromatic cyclization reaction under the action of corresponding alkali at a certain temperature to synthesize the pyrazole compound containing the modifiable functional group. The preparation method provided by the invention has the advantages that the operation is simple, the raw materials are easy to obtain, the tolerance of reacted functional groups is good, a plurality of substituent groups can be introduced simultaneously, and the product is easy to separate.

Description

technical field [0001] The invention belongs to a compound synthesis method, in particular to a pyrazole compound and a preparation method thereof. Background technique [0002] Pyrazoles and their derivatives are an important class of parent nucleus structures in many agrochemicals, materials and pharmaceutical chemistries, for example, the most successful non-steroidal antidepressants celecoxib and tepoxalin are selective cycloaddition Oxygenase 2 (COX-2) inhibitors contain a pyrazole core in their structure. Rimonabant, a selective CB1 cannabinoid receptor inverse agonist for the treatment of obesity, and Fipronil, an insecticide, also contain pyrazole nuclei. The structural formula is as follows: [0003] [0004] At present, the synthesis methods of pyrazole compounds mainly include: 1) synthesis by reacting 1,3 unsaturated carbonyl compounds or analogs with hydrazine or substituted hydrazines; chemical reaction synthesis. [0005] In the process of realizing the...

Claims

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Application Information

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IPC IPC(8): C07D231/12C07D401/04C07D405/04
CPCC07D231/12C07D401/04C07D405/04
Inventor 祝华建邵加安张建康吴兆晓施涛贾婷婷
Owner ZHEJIANG UNIV CITY COLLEGE