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Synthesis method of 4,6-dichloro-1H-imidazo [4,5-C] pyridine-2(3H)-ketone

A synthetic method, imidazolo technology, applied in the field of synthesis of 4,6-dichloro-1H-imidazo[4,5-C]pyridin-2-one, which can solve the problem of waste acid and waste residue and unenvironmental reagents , high cost and other issues, to achieve the effect of reducing production cost, low value and low cost

Inactive Publication Date: 2018-08-24
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore existing synthetic method all has various defectives, or reagent is not environmentally friendly, or yield is lower, or too much waste acid and waste residue cause cost comparatively expensive
The existing technical routes need to be improved in terms of environmental friendliness and cost

Method used

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  • Synthesis method of 4,6-dichloro-1H-imidazo [4,5-C] pyridine-2(3H)-ketone
  • Synthesis method of 4,6-dichloro-1H-imidazo [4,5-C] pyridine-2(3H)-ketone
  • Synthesis method of 4,6-dichloro-1H-imidazo [4,5-C] pyridine-2(3H)-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) In a four-neck flask equipped with mechanical stirring, reflux condenser, and thermometer, put 20 grams of compound 1 into 30 grams of ethanol, stir until it is completely dissolved, pass through ammonia gas to raise the temperature to 25°C, and keep it warm at 25-30°C After 24 hours, after monitoring the completion of ammonolysis, the organic solvent was recovered, the residue was cooled, filtered, washed, and dried to obtain a total of 17.71 g of compound 2, with a yield of 95% based on compound 1.

[0030] 2) In a four-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer, put 20 grams of compound 2 into tetrahydrofuran, stir, add an equivalent amount of LDA, stir for 30 minutes at 0° C., and then add dropwise fresh sodium hypochlorite (11 %) 25 grams, after the dropwise addition was completed, insulated and stirred for 2 hours. After the reaction, the temperature was raised to 70°C, and the temperature was kept at 70-75°C for 3 ho...

Embodiment 2

[0032] 1) In a four-neck flask equipped with mechanical stirring, reflux condenser and thermometer, put 20 grams of compound 1 into 30 grams of toluene, stir until completely dissolved, feed ammonia gas to raise the temperature to 10°C, and keep it warm at 0-15°C After 24 hours, the ammonolysis was monitored completely, the organic solvent was recovered, the residue was cooled, filtered, washed, and dried to obtain 16.78 g of compound 2, with a yield of 90% based on compound 1.

[0033] 2) In a four-necked flask equipped with mechanical stirring, a reflux condenser, and a thermometer, put 20 grams of compound 2 into tetrahydrofuran, add an equivalent amount of lithium hexamethyldisilazide under stirring, and stir at 20°C for 30 minutes. 25 grams of fresh sodium hypochlorite (11%) was added dropwise, and after the dropwise addition was completed, the mixture was incubated and stirred for 2 hours. After the reaction, the temperature was raised to 70°C, and the temperature was ke...

Embodiment 3

[0035] 1) In a four-necked flask equipped with mechanical stirring, reflux condenser, and thermometer, put 20 grams of compound 1 into 30 grams of methanol, stir until it is completely dissolved, pass through ammonia gas to raise the temperature to 10°C, and keep it warm at 10-25°C After 24 hours, after monitoring the completion of ammonolysis, the organic solvent was recovered, the residue was cooled, filtered, washed, and dried to obtain a total of 17.12 g of compound 2, with a yield of 91.8% based on compound 1.

[0036]2) In a four-neck flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer, put 20 grams of compound 2 into tetrahydrofuran, stir, add an equivalent amount of butyllithium, stir at -10°C for 30 minutes, and then add fresh Sodium hypobromite (11%) 30 grams, after dropwise addition is completed, keep stirring for 2 hours. After the reaction, the temperature was raised to 50°C, and the temperature was kept at 50-55°C for 3 hours. After th...

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Abstract

The invention discloses a synthesis method of 4,6-dichloro-1H-imidazo [4,5-C] pyridine-2(3H)-ketone. The synthesis method comprises the following steps: with 2,6-dichloro-3-amino-4-pyridine methyl formate as a main starting material, feeding ammonia gas into a solvent for ammonolysis reaction, simply treating the product to obtain a compound 2, and directly performing Hofmann rearrangement and cyclization, thereby obtaining a target compound 3 under a proper condition. Compared with an existing line, the line has relatively short steps, and the whole line basically comprises unit reaction; theoperation is simple, and conditions are mild; the target compound can be obtained by simple treatment; the whole line is relatively high in yield; and by application of the line for production, greateconomical and social benefits are achieved. In short, the synthesis method disclosed by the invention has the following characteristics of mild reaction conditions, simple technological operation, environmental friendliness, low cost and high yield.

Description

technical field [0001] The invention relates to a synthesis method of 4,6-dichloro-1H-imidazo[4,5-C]pyridin-2(3H)-one. Background technique [0002] 4,6-Dichloro-1H-imidazo[4,5-C]pyridin-2(3H)-one, is a drug for the treatment or prevention of headaches involving changes in CGRP (calcitonin gene-related peptide) receptor antagonists , an important intermediate of new drugs for migraine and cluster headache, the CAS number is [668268-68-6], and the molecular formula is as follows: [0003] [0004] The compound is a class of drugs for the treatment of headaches, migraines and cluster headaches caused by changes in the content of CGRP (calcitonin gene-related peptide) receptor antagonists. This compound is a single (or multiple) cyclic anilide spiro Lactam CGRP receptor antagonist. [0005] 4,6-Dichloro-1H-imidazo[4,5-C]pyridin-2(3H)-one is an important intermediate of this new drug. Literature reports 4,6-dichloro-1H-imidazo[4,5-C]pyridin-2(3H)-one synthetic method mainl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 李健新赵大同张治国徐相雨黄剑程红伟
Owner JIANGSU YUXIANG CHEM
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