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Preparation method of 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile

A 2-a, imidazolo technology, applied in the field of preparation of 2-(imidazo[1,2-a]pyridin-3-yl)acetonitrile, can solve the problems of less raw material sources, difficult industrial production, high price, etc. Achieve the effect of reducing energy consumption, reducing pollution and low cost

Inactive Publication Date: 2013-01-23
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] This process uses 3-imidazo[1,2-a]pyridinecarbaldehyde as the starting raw material. The source of raw materials in this synthesis method is less, and the price of the reaction reagent p-toluenesulfonylmethyl isonitrile is relatively high, so it is difficult to industrialize production

Method used

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  • Preparation method of 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile
  • Preparation method of 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile
  • Preparation method of 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile

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Embodiment 1

[0036] Add 300g of 60% 2,2-dimethoxyacetaldehyde aqueous solution, 3800mL of cyclohexane and 600g of diethyl cyanomethyl phosphate into a 5L round bottom flask, and add in batches at an ice bath to control the internal temperature at 0-5°C 280g of 50% sodium methoxide methanol was added and reacted at room temperature for 2 hours. After the reaction was completed, 7600 mL of water was added, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was concentrated under reduced pressure to obtain a colorless oily liquid, which was distilled under reduced pressure to obtain 4,4 -Dimethoxy-2-butenenitrile 201.25g, yield 91.56%.

Embodiment 2

[0038] Add 300g of 60% 2,2-dimethoxyacetaldehyde aqueous solution, 3800mL of cyclohexane and 600g of diethyl cyanomethyl phosphate into a 5L round bottom flask, add 500g of 28% diethyl phosphate dropwise in an ice bath to control the internal temperature at 10-25°C Sodium methoxide methanol solution was added and reacted at room temperature for 3h. After the reaction was completed, 7600 mL of water was added, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was concentrated under reduced pressure to obtain a colorless oily liquid, which was distilled under reduced pressure to obtain 4,4 -Dimethoxy-2-butenenitrile 215.58g, yield 98.08%.

Embodiment 3

[0040] Add 300g of 60% 2,2-dimethoxyacetaldehyde aqueous solution, 3800mL of cyclohexane and 600g of diethyl cyanomethyl phosphate into a 5L round bottom flask, and add 700g of concentration dropwise in an ice bath to control the internal temperature at 10-25°C It is 20% sodium methoxide methanol solution, and the reaction is completed at room temperature for 3 hours. After the reaction was completed, 7600 mL of water was added, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was concentrated under reduced pressure to obtain a colorless oily liquid, which was distilled under reduced pressure to obtain 4,4 -Dimethoxy-2-butenenitrile 203.65g, yield 92.65%.

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Abstract

The invention relates to a preparation method of 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile, which comprises the following steps: (1) performing condensation reaction on 2,2-dimethoxy acetaldehyde and ethyl cyanomethylphosphonate to prepare 4,4-dimethoxy-2-crotononitrile, wherein the reaction solvent is cyclohexane, the catalyst is a sodium methoxide-methanol solution, the reaction temperature is 0-25 DEG C, and the reaction time is 2-4 hours; and (2) performing ring-closure reaction on the 4,4-dimethoxy-2-crotononitrile and 2-aminopyridine or hydrochloride thereof to prepare the 2-(imidazo-[1,2-a]pyridyl-3-yl)acetonitrile, wherein in the step (1), the cyanomethylphosphoric acid diester is dimethyl cyanomethylphosphonate or diethyl cyanomethylphosphonate. The invention has the advantages of easily available raw materials, safety in use, mild reaction conditions, high controllability, low cost, favorable product quality and high yield, and is suitable for forming large-scale production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of 2-(imidazo[1,2-a]pyridin-3-yl)acetonitrile, 2-(imidazo[1,2-a]pyridin-3-yl) Acetonitrile can be used as an important intermediate in the preparation of Glycogen Synthase Kinase-3 (GSK3) inhibitor (CAS: 603288-22-8) and anti-osteoporosis drug minodronic acid. Background technique [0002] Glycogen Synthase Kinase 3 Inhibitor (CAS: 603288-22-8) is a potential drug for the treatment of type 2 diabetes. Glycogen Synthase Kinase 3 (Glycogen Synthase Kinase-3, GSK3) is a silk (Su) Amino acid protein kinase is encoded by two relatively independent genes, but the sequence of the catalytic region is 98% identical. GSK3 can phosphorylate glycogen synthase (Glycogen Synthase, GS) to block glycogen synthesis, while GSK3 inhibitors can promote glycogen synthesis and reduce plasma glucose concentration. GSK3 is also now recognized as a key part of multiple signaling p...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 戈文兰苗燕飞高盼陈国广
Owner NANJING UNIV OF TECH
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