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Method for preparing medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative

A technology of diarylpyridine and 10-, which is applied in the field of biomedicine preparation, can solve the problems of long reaction time, low yield, complex product purification process, etc., and achieve short reaction time, reduction of side reactions, catalytic activity and selectivity high effect

Active Publication Date: 2020-07-10
马鞍山市泰博化工科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Finally, the reaction time is longer in the whole preparation process, the yield is lower and the purification process of the product is more complicated

Method used

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  • Method for preparing medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative
  • Method for preparing medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative
  • Method for preparing medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 1.0mmol p-bromobenzaldehyde, 1.2mmol Aniline, 2.0 mmol of 2,4-dione piperidine and 0.07 mmol of acidic ionic liquid catalyst were stirred at room temperature until uniform. Evenly heated to reflux (solvent vapor does not exceed the second ball of the spherical condenser), kept reflux for 81 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, the reaction solution was cooled to room temperature, and a large amount of solids were precipitated. After filtration, the filter residue was washed with water (5ml×3) and dried under vacuum at 80°C for 48h to obtain 0.43g of 10-(4-bromophenyl)-5-phenyl-3,4,6,7,8,10-hexahydro The purity of pyrido[4,3-b][1,6]naphthyridine-1,9(2H,5H)-dione determined by high performance liquid chromatography was 98.5%, and the calculated yield was 93%. Add p-bromobenzaldehyde, aniline and 2,4-piperidinedione directly to the filtrate for repeated use.

[0025] The product obtained in this example 10-(4-bromoph...

Embodiment 2

[0027]Add 1.0mmol p-bromobenzaldehyde, 1.2mmol p-Bromoaniline, 2.0mmol 2,4-piperidinedione and 0.07mmol acidic ionic liquid catalyst were stirred evenly at room temperature. Heating evenly to reflux (the solvent vapor does not exceed the second ball of the spherical condenser tube), keep reflux for 88min, TLC (thin plate chromatography) detection, the raw material point disappears, the reaction solution is cooled to room temperature, and a large amount of solid is precipitated. After filtering, the filter residue was washed with water (5ml×3) and dried under vacuum at 80°C for 48h to obtain 0.47g of 5,10-bis(4-bromophenyl)-3,4,6,7,8,10-hexahydropyridine And[4,3-b][1,6]naphthyridine-1,9(2H,5H)-dione has a purity of 98.3% as determined by high performance liquid chromatography and a calculated yield of 88%. Add p-bromobenzaldehyde, p-bromoaniline and 2,4-piperidinedione directly to the filtrate for repeated use.

[0028] The product obtained in this example, 5,10-bis(4-bromoph...

Embodiment 3

[0030] Add 1.0mmol p-chlorobenzaldehyde, 1.1mmol p-Chloroaniline, 2.0mmol 2,4-piperidinedione and 0.06mmol acidic ionic liquid catalyst were stirred evenly at room temperature. Heating evenly to reflux (the solvent vapor does not exceed the second ball of the spherical condenser tube), keep reflux for 84min, TLC (thin plate chromatography) detection, the raw material point disappears, the reaction solution is cooled to room temperature, and a large amount of solid is precipitated. After filtering, the filter residue was washed with water (5ml×3) and dried under vacuum at 80°C for 48h to obtain 0.38g of 5,10-bis(4-chlorophenyl)-3,4,6,7,8,10-hexahydropyridine And[4,3-b][1,6]naphthyridine-1,9(2H,5H)-dione has a purity of 98.8% as determined by high performance liquid chromatography and a calculated yield of 86%. Add p-chlorobenzaldehyde, p-chloroaniline and 2,4-piperidinedione directly to the filtrate for repeated use.

[0031] The product obtained in this example, 5,10-bis(4-c...

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Abstract

The invention discloses a method for preparing a medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative, and belongs to the technical field of biological medicine preparation. The method for preparing the medical intermediate 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative by acidic ionic liquid catalysis includes: taking aromatic aldehyde, amine and 2, 4-piperidinedione as the reaction raw materials, adopting an ethanol-dimethylformamide-water mixed solution as a reaction solvent, and performing catalysis by an acidic ionic liquid catalyst to obtain the 5, 10-diarylpyrido[4, 3-b][1, 6]naphthyridine derivative. The preparation process provided by the invention has the advantages of high product yield, recyclable catalytic system, short reaction time, simpleand convenient product purification process and the like.

Description

technical field [0001] The invention belongs to the technical field of biomedicine preparation, and in particular relates to a method for preparing pharmaceutical intermediate 5,10-diarylpyrido[4,3-b][1,6]naphthyridine derivatives by catalyzing an acidic ionic liquid. Background technique [0002] Nalidixic compounds are bicyclic heterocyclic compounds that are fused and have two nitrogen atoms, and have good biological activity and pharmacological activity. Genus, Shigella, Enterobacter, Escherichia coli, Salmonella, and Haemophilus influenzae have antibacterial activity. As one of the naphthyridine compounds, [1,6]naphthyridine derivatives have attracted extensive attention in the fields of drug synthesis and medicine in recent years due to their structural diversity and various biological and pharmacological activities. [0003] Ionic liquids are composed of organic cations and inorganic or organic anions, and are liquid at room temperature with certain fluidity. The ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14
CPCC07D471/14
Inventor 卢华
Owner 马鞍山市泰博化工科技有限公司
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