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Synthesis method of 1, 5-benzodiazepine derivative

A technology of benzodiazepine and synthesis method, applied in 1 field, can solve problems such as limitation and low atom economy, and achieve the effects of stable storage and access, easy storage and access, and high yield

Active Publication Date: 2012-09-26
PINGHU QIANFENG MASCH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these strategies can provide effective methods for the synthesis of 1,5-benzodiazepine derivatives, these strategies inevitably produce side effects during the synthesis of 1,5-benzodiazepine derivatives. products (such as water, hydrogen halide, etc.), which in turn lead to lower atom economy, limiting the application of such strategies

Method used

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  • Synthesis method of 1, 5-benzodiazepine derivative
  • Synthesis method of 1, 5-benzodiazepine derivative
  • Synthesis method of 1, 5-benzodiazepine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039]In a 15ml reactor, sequentially add 21.6mg (0.2mmol) of o-phenylenediamine, 51.1mg (0.5mmol) of phenylacetylene, [bis(trifluoromethanesulfonimide)][2-(dicyclohexylphosphino )] Gold (I) 8.3 mg (0.01 mmol) and chloroform (2 mL). Then, the mixture was stirred and reacted at 60° C. for 6 hours. TLC (developing agent ratio: petroleum ether to ethyl acetate volume ratio 10:1) detection After the reaction is completed, 100-200 mesh silica gel (0.5g) is added to the reaction mother liquor, the solvent is removed under reduced pressure, and the obtained residue is directly added to the silica gel column. , separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 10:1), collected the eluate and evaporated the solvent to obtain a yellow solid 2-methyl-2,4-diphenyl Dihydro-2,3-dihydro-1H-1,5-benzodiazepine 58.1 mg (93% yield). Product characterization: Yellow solid; mp 150-152°C (lit.mp 150-152°C); IR (KBr): v=3336, 3057, 2971, 16...

Embodiment 2

[0041]

[0042] In a 15ml reactor, sequentially add 21.6mg (0.2mmol) of o-phenylenediamine, 58.1mg (0.5mmol) of p-methylphenylacetylene, [bis(trifluoromethanesulfonimide)][2-(bicyclic Hexylphosphino)] gold (I) 8.3 mg (0.01 mmol) and chloroform (2 mL). Then, the mixture was stirred and reacted at 60° C. for 6 hours. TLC (developing agent ratio: petroleum ether to ethyl acetate volume ratio 10:1) detection After the reaction is completed, 100-200 mesh silica gel (1.0 g) is added to the reaction mother liquor, the solvent is removed under reduced pressure, and the obtained residue is directly added to the silica gel column. , separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 10:1), collected the eluate and evaporated the solvent to obtain a yellow solid 2-methyl-2,4-xylene Dihydro-2,3-dihydro-1H-1,5-benzodiazepine 62.6 mg (92% yield). Product characterization: Yellow solid; mp 99-100°C (lit.mp98-99°C); IR (KBr): v=3336, 2969, 292...

Embodiment 3

[0044]

[0045] In a 15ml reactor, 21.6mg (0.2mmol) of o-phenylenediamine, 66.1mg (0.5mmol) of p-methoxyphenylacetylene, [bis(trifluoromethanesulfonimide)][2-(di Cyclohexylphosphino)] gold (I) 8.3 mg (0.01 mmol) and chloroform (2 mL). Then, the mixture was stirred and reacted at 60° C. for 6 hours. TLC (developing agent ratio: petroleum ether to ethyl acetate volume ratio 10:1) detection After the reaction is completed, 100-200 mesh silica gel (1.0 g) is added to the reaction mother liquor, the solvent is removed under reduced pressure, and the obtained residue is directly added to the silica gel column. , separated by column chromatography (eluent ratio: petroleum ether to ethyl acetate volume ratio 10:1), collected the eluate and evaporated the solvent to obtain a yellow solid 2-methyl-2,4-dimethyl Oxyphenyl-2,3-dihydro-1H-1,5-benzodiazepine 60.3 mg (81% yield). Product characterization: Yellow solid; mp 118-120°C (lit.mp 114-116°C); IR (KBr): v=3338, 3052, 2963, 1604, ...

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Abstract

The invention discloses a synthesis method of a 1, 5-benzodiazepine derivative, which is obtained by an intermolecular amination / cyclization tandem reaction process of an o-phenylene diamine compound and an alkyne compound in the presence of a catalyst. The method of the invention is characterized in that the alkyne is used as a starting material for the first time and utilization ratio of reacted atoms is 100%. The method further has good general adaptability for various substituent groups.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 1,5-benzodiazepine derivatives (2) Background technology [0002] As an important heterocyclic compound with pharmacological activity, benzodiazepine derivatives are widely used in the preparation of anti-inflammatory drugs, anticonvulsants, anxiolytics, sedatives, hypnotics, etc. In addition, 1,5-benzodiazepine derivatives are also used as raw materials for the synthesis of fused ring compounds, such as triazoles, oxadiazoles, oxazinones and furan benzodiazepines. [0003] At present, the typical synthesis strategy of 1,5-benzodiazepine derivatives is mainly through condensation / cyclization between o-phenylenediamine and α,β-unsaturated carbonyl compounds or β-haloketones or ketones to achieve. Although these strategies can provide effective methods for the synthesis of 1,5-benzodiazepine derivatives, these strategies inevitably produce side effects during the synthesis of 1,5-benzodiazepine der...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D243/12C07D409/14
Inventor 刘运奎钱建强徐振元
Owner PINGHU QIANFENG MASCH CO LTD
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