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Fluorine-containing benzo [d]-1, 3-oxazepine compound and synthesis method thereof

An oxazepine and compound technology, applied in the field of organic synthesis, can solve problems such as low yield, and achieve the effects of convenient operation, inhibition of side reactions and good tolerance

Pending Publication Date: 2022-03-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction is affected by side reactions and the yield is low

Method used

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  • Fluorine-containing benzo [d]-1, 3-oxazepine compound and synthesis method thereof
  • Fluorine-containing benzo [d]-1, 3-oxazepine compound and synthesis method thereof
  • Fluorine-containing benzo [d]-1, 3-oxazepine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of Compound 4-fluoro-1,4,7-trimethyl-4,5-dihydrobenzo[d][1,3]oxazepin-2(1H)-one(2a)

[0024]

[0025] Add raw material tert-butyl me-thyl(4-methyl-2-(prop-1-en-2-yl)phenyl)carbamate (1a, 26.1 mg) to a glass test tube, then add tris(dibenzylidene)acetone Dipalladium (4.6mg, 0.05 equivalent) and anhydrous sodium sulfate (14.1mg, 1 equivalent), then add acetonitrile (1ml) and dichloromethane (1ml), finally add 1-chloromethyl-4-fluoro-1, 4-Diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt (71 mg, 2 equivalents) was reacted with stirring at 25°C. In the course of the reaction, the reaction was followed and monitored with a TLC plate, and the reaction was complete in about 4 hours. The reaction solution was then filtered using a short silica gel column, and the filter cake was washed with ethyl acetate. After the filtrate was collected, the solvent was distilled off under reduced pressure and the residue was separated by silica gel chromatography to obtain ...

Embodiment 2

[0027] Synthesis of Compound 4-fluoro-8-methoxy-1,4-dimethyl-4,5-dihydrobenzo[d][1,3]oxazepin-2(1H)-one(2f)

[0028]

[0029] Add the raw material tert-butyl me-thyl(5-methoxy-2-(prop-1-en-2-yl)phenyl)carbamate (1f, 27.7mg) to the glass test tube, then add tris(dibenzylidene)acetone Dipalladium (4.6mg, 0.05 equivalents) and anhydrous sodium sulfate (28.2mg, 2 equivalents), then add acetonitrile (1ml) and dichloromethane (1ml), and finally add (69 mg, 2 equivalents), and the stirring reaction was carried out at 5°C. During the reaction, the reaction was followed and monitored by TLC plate, and the reaction was complete in about 24 hours. The reaction solution was then filtered using a short silica gel column, and the filter cake was washed with ethyl acetate. After the filtrate was collected, the solvent was distilled off under reduced pressure and the residue was separated by silica gel chromatography to obtain 11 mg of product 2f with a yield of 44%. NMR data: 1H NMR ...

Embodiment 3

[0031] Synthesis of Compound 4-fluoro-1-methyl-4-(pyrrolidine-1-carbonyl)-4,5-dihydrobenzo[d][1,3]oxazepin-2(1H)-one(2o)

[0032]

[0033] Add raw materials tert-butyl me-thyl (2-(3-oxo-3-(pyrrolidin-1-yl) prop-1-en-2-yl) phenyl) carbamate (1o, 33.0mg), acetic acid to the glass test tube Palladium (2.3mg, 0.1 equivalent), and anhydrous sodium sulfate (14.1mg, 1 equivalent), then add acetonitrile (2ml), and finally add 1-chloromethyl-4-fluoro-1,4-diazabicyclo[ 2.2.2] Octane bis(tetrafluoroborate) salt (40mg, 1.1 equivalents), stirred and reacted at 40°C. During the reaction, the reaction was followed and monitored by TLC plate, and the reaction was complete in about 3 hours. The reaction solution was then filtered using a short silica gel column, and the filter cake was washed with ethyl acetate. After the filtrate was collected, the solvent was distilled off under reduced pressure, and the residue was separated by silica gel chromatography to obtain 23 mg of product 2o wi...

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Abstract

The invention relates to a fluorine-containing benzo [d]-1, 3-oxazepine compound and a synthesis method thereof. According to the synthesis method, o-aminobenzene propene molecules protected by N-t-butyloxycarboryl (Boc) are used as a substrate, and react with a fluorine reagent under the catalysis of palladium to prepare the compound. The preparation method of the fluorine-containing benzo [d]-1, 3-oxazepine structure compound comprises the following steps: dissolving N-Boc protected o-aminobenzene propylene molecules in a solvent, and reacting with a fluorine reagent under the catalysis of palladium at a certain temperature to obtain the fluorine-containing benzo [d]-1, 3-oxazepine structure compound. The synthesis method is mild in condition and relatively good in yield, has tolerance of various functional groups, can be used for constructing various fluorinated heteroAndroid structures, and has potential application in the fields of biology, medicines, pesticides and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a fluorine-containing benzo[d]-1,3-oxazepine compound and a synthesis method thereof, which have broad application prospects in the fields of biology, medical treatment, pesticides and the like. Background technique [0002] Heterocyclic compounds widely exist in natural products, and they have been deeply researched and applied in the fields of biology, medicine and materials. Among them, the oxazepine structure is widely used in the field of pesticides in the field of biomedical science. For example, in the patent WO2006 / 116764A1 "Polycyclic carbamoylpyridone derivative having HIV integraseinhibitory activity and their preparation", a class of molecules containing the oxazepine structure has been invented. Good anti-HIV efficacy; patent WO1997JP00754 "5,11-dihydrodibenzo[b,e][1,4]oxazepine derivatives and pharmaceutical compositions containing the same" invented a dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/06
CPCC07D267/06
Inventor 吴宏描吴益栋邢卫红
Owner NANJING UNIV OF TECH
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