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Synthesis method of medicine intermediate carbamate compounds

A carbamate and synthesis method technology, applied in the field of pharmaceutical compound synthesis, can solve problems affecting the large-scale production and utilization of compounds, low product yield, environmental pollution, etc., and achieve good application prospects

Active Publication Date: 2017-03-29
聊城高新区量子生物医药产业发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, these existing methods still have some defects, such as low product yield, environmental pollution, complicated operation, high cost, etc., which seriously affect the large-scale production and utilization of this type of compound.
[0005] In order to overcome the shortcomings of the above-mentioned low yield, environmental pollution, complicated operation, high cost, etc. that exist in the synthesis method of carbamate compounds in the prior art, the inventors have carried out in-depth research on the preparation method of this type of compound, thus obtaining A new synthetic method of carbamate compound

Method used

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  • Synthesis method of medicine intermediate carbamate compounds
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  • Synthesis method of medicine intermediate carbamate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 100 ml of a mixed organic solvent of N,N-dimethylformamide and acetonitrile with a volume ratio of 2:1 to the reactor, and add 10 mmol of the compound of the above formula (I) and 12 mmol of the compound of the above formula (II) to it in turn , 1.2 mmol catalyst bis(triphenylphosphine) nickel chloride (NiCl 2 (PPh 3 ) 2 ), 2.0 mmol of ligand L1, heated to 50°C while stirring, and stirred and reacted at this temperature for 1 hour. After the reaction was complete, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the organic phase was desolvated, and the resulting residue was separated by 300-400 mesh silica gel column chromatography, and the elution solvent was ethyl acetate with a volume ratio of 2:8. The mixture of hexane can obtain the above-mentioned compound of formula (III), and the productive rate is 94.7%.

[0026] 1 H NMR (CDCl 3 , 400 MHz): δ 10.19 (s, 1H), 7.90 (d, J = 7.6 Hz, 1H),7.62 (t, J = 7.6 Hz, 1H)...

Embodiment 2

[0028]

[0029] Add 100 ml of a mixed organic solvent of N,N-dimethylformamide and acetonitrile with a volume ratio of 2:1 to the reactor, and add 10 mmol of the compound of the above formula (I) and 12 mmol of the compound of the above formula (II) to it in turn , 1.6 mmol catalyst bis(triphenylphosphine) nickel chloride (NiCl 2 (PPh 3 ) 2 ), 2.0 mmol of ligand L1, heated to 50°C while stirring, and stirred and reacted at this temperature for 1 hour. After the reaction was completed, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the solvent was removed from the organic phase, and the resulting residue was separated by 300-400 mesh silica gel column chromatography to obtain the compound of formula (III) with a yield of 90.7%. . 1 H NMR ( d 6 -DMSO, 400 MHz): δ 10.14 (s, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.69 (d, J =8.0 Hz, 1H), 7.30 (t, J = 8.0 Hz, 1H) , 3.41-3.58 (m, 4H), 1.19-1.38 (m, 6H)ppm.

Embodiment 3

[0031]

[0032] Add 100 ml of a mixed organic solvent of N,N-dimethylformamide and acetonitrile with a volume ratio of 2:1 to the reactor, and add 10 mmol of the compound of the above formula (I) and 12 mmol of the compound of the above formula (II) to it in turn , 1.2 mmol catalyst bis(triphenylphosphine) nickel chloride (NiCl 2 (PPh 3 ) 2 ), 2.0 mmol of ligand L1, heated to 50°C while stirring, and stirred and reacted at this temperature for 1 hour. After the reaction was completed, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the solvent was removed from the organic phase, and the resulting residue was separated by 300-400 mesh silica gel column chromatography to obtain the compound of formula (III) with a yield of 95.7%. . 1 H NMR (CDCl 3 , 400 MHz): δ10.04 (s, 1H), 7.84 (d, J = 8.8 Hz, 1H), 7.73-7.88 (m,2H), 3.88(s, 3H), 3.68 (br m, 2H), 3.53 (br m, 2H), 1.66 (br 6H) ppm.

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Abstract

The invention provides a synthesis method of medicine intermediate carbamate compounds. Compounds disclosed as Formula (I) and compounds disclosed as Formula (II) react in an organic solvent in the presence of a catalyst and a ligand to obtain carbamate compounds. The method implements high-yield synthesis of carbamate compounds, and has favorable application prospects.

Description

technical field [0001] The invention relates to a synthesis method of a pharmaceutical intermediate compound, more particularly to a synthesis method of a carbamate compound, and belongs to the field of synthesis of pharmaceutical compounds. Background technique [0002] The carbamate structure is a very important class of active groups in organic chemical synthesis. It exists in various biologically active molecules and is one of the important skeleton structures of many pharmaceutically active compounds. Carbamate compounds, as intermediates in drug synthesis, can be expanded and modified through a variety of reactions to obtain biologically active compounds, which play an important role in organic chemical synthesis. [0003] In recent years, more and more attention has been paid to the development of synthetic methods of carbamate compounds, a lot of research has been done on it, and some new synthetic routes and methods have been obtained. So far, various synthesis met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/44C07C269/00C07D295/205
CPCC07C269/00C07D295/205C07C271/44
Inventor 孙伟之徐超
Owner 聊城高新区量子生物医药产业发展有限公司
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