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Simple synthesis method of 2-aminothiophene derivative

A technology of aminothiophene and synthesis method, which is applied in the field of pharmaceutical biochemical industry, can solve the problems of restricting the industrial application of synthesis technology, serious environmental pollution, and high cost of raw materials, and achieve the effects of easy industrial application, simple synthesis steps, and less stringent temperature control

Active Publication Date: 2015-07-01
XINFA PHARMA
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Problems solved by technology

[0007] This route also does not avoid the application of raw materials such as hydrazine hydrate. The steps are cumbersome, the cost of raw materials is high, and the environmental pollution is serious. The above reasons severely limit the use of 2-amino-3-(4-chloro)benzoyl-4-(N-alkyl) / Arylpiperazine-N′-)Methylthiophene Synthetic Process Industrial Application

Method used

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  • Simple synthesis method of 2-aminothiophene derivative
  • Simple synthesis method of 2-aminothiophene derivative
  • Simple synthesis method of 2-aminothiophene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, N-methyl-N'-acetylmethylpiperazine

[0041] Add 100g (1mol) of methylpiperazine to 600ml of DMF, add 1.2mol of anhydrous potassium carbonate, control the temperature between 30-40°C, and slowly add 1.1mol of monochloroacetone dropwise under strong stirring. After completion, keep warm at 30-40°C for 3 hours, and take samples for GC detection. After the reaction is qualified, the solvent is recovered under reduced pressure at 50°C until some material is precipitated, which is N-methyl-N'-acetylmethylpiperazine. Cool down to room temperature, add 200ml of pure water and 200ml of ethyl acetate for extraction, washing and desalination. The aqueous phase was washed 3 times with 50 ml of ethyl acetate. Combine the ethyl acetate layers, wash the ethyl acetate layer with water, wash with brine, dry over anhydrous magnesium sulfate, and concentrate to dryness to obtain 127.3 g of the product N-methyl-N-acetylmethylpiperazine with a gas phase purity of 98.9% (area ...

Embodiment 2

[0042] Embodiment 2, N-ethyl-N-acetylmethylpiperazine

[0043] As described in Example 1, the difference is that ethylpiperazine is used to replace piperazine, and the remaining conditions are the same as in Example 1. The results obtained are shown in Table 1.

Embodiment 3

[0044] Embodiment 3, N-n-propyl-N-acetylmethylpiperazine

[0045] As described in Example 1, the difference is that methylpiperazine in Example 1 is replaced by n-propylpiperazine, and the rest of the conditions are the same, and the results are shown in Table 1.

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Abstract

The invention relates to a simple synthesis method of a 2-aminothiophene derivative. The method comprises the steps of condensating monochloroacetone, alkyl / aryl-piperzine under the effect of inorganic base to prepare a piperzine derivative II, mixing the piperzine derivative II with 4-chlorobenzoyl acetonitrile and sulphur, dropping organic amine, performing heat preservation reaction, and reacting in two steps to obtain 2-amino-3,(4- chlorine)-benzoyl-4-(N- alkyl / aryl-piperzine-N '-) methylthiophene. The simple synthesis method of the 2-aminothiophene derivative is available in raw materials, simple to operate, simple in synthesis steps and environmental-friendly; meanwhile, products are high in selectivity, yield and purity and applicable to industrial application.

Description

technical field [0001] The invention relates to a convenient synthesis method of 2-aminothiophene derivatives, which belongs to the technical field of medicine, biochemical industry. Background technique [0002] Extracellular purines and pyrimidines are important signaling molecules. They can exert biological effects through receptors on the cell membrane. These receptors are mainly divided into two families, P1 and P2. The P1 receptor family (also known as adenosine receptor) There are four subtypes, A1, A2a, A2b, and A3. The A1 adenosine receptor allosteric enhancer, 2-amino-3-(4-chloro)benzoyl-4-(N-alkyl / arylpiperazine-N′-)methylthiophene, can be used in the treatment of A1 adenosine receptor mediated disorders. It is mentioned in CN200980116511.7 that the A1 adenosine receptor allosteric enhancer is a class of compounds that show enhanced adenosine A1 receptor function by stabilizing the high-affinity state of the adenosine A1 receptor-G-protein complex , this proper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/36
CPCC07D333/36
Inventor 戚聿新李新发鞠立柱张明峰
Owner XINFA PHARMA
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