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Preparation method of 3-(2-pyridineamino)ethyl propionate

A kind of technology of ethyl propionate and pyridyl amino, applied in the field of preparation of ethyl 3-propionate, can solve the problems of long synthesis steps, long reaction time and high production cost, and achieves low production cost, short reaction time and convenient operation Effect

Inactive Publication Date: 2013-04-24
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention solves the synthesis step in the preparation and production of intermediate product 3-(2-pyridylamino) ethyl propionate used in the synthesis process of dabigatran etexilate long time, complex operation, long reaction time, high production cost and other problems, it provides a preparation method with low cost of raw materials, short synthesis steps, simple operation, recyclable catalyst, short operation time and high yield

Method used

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  • Preparation method of 3-(2-pyridineamino)ethyl propionate

Examples

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Embodiment 1

[0028] A kind of preparation method of 3-(2-pyridylamino) ethyl propionate, the steps are as follows:

[0029] Add 2-aminopyridine (0.47g, 5mmol) and ethyl acrylate (1.0g, 10mmol) to four 25mL round bottom flasks or 15mL sealed tubes, respectively, and then add perchloric acid (0.5 g, 0.5mmol), 200-300 mesh silica gel loaded perchloric acid (0.5g, 0.5mmol), 300-400 mesh silica gel loaded perchloric acid (0.5g, 0.5mmol), silica gel H loaded perchloric acid ( 0.5g, 0.5mmol) as the catalyst, under the condition of ethanol (2mL) as the organic solvent, the reaction temperature was controlled at 100°C for 24h, the reaction mother liquor obtained after the reaction was separated by a centrifuge, the supernatant was taken, and the supernatant The supernatant liquid is concentrated at a temperature of 40-45°C and a pressure of 0.09-0.1 MPa under reduced pressure. The concentrated liquid is passed through a silica gel column or an aluminum oxide column with a ratio of petroleum ether:e...

Embodiment 2

[0032] A kind of preparation method of 3-(2-pyridylamino) ethyl propionate, the steps are as follows:

[0033] Add 2-aminopyridine (0.47g, 5mmol) and ethyl acrylate (1.0g, 10mmol) into a 25mL round bottom flask or a 15mL sealed tube, add perchloric acid (0.5g 0.5mmol) loaded on 200-300 mesh silica gel Catalyst, ethanol (2mL) as solvent, control the temperature at 100°C for 24 hours, separate the reaction mother liquor obtained after the reaction with a centrifuge, take the supernatant, control the temperature of the supernatant at 40-45°C, and the pressure at 0.09- Concentrate under reduced pressure at 0.1MPa, and the concentrated solution is subjected to column chromatography with a silica gel column or an aluminum oxide column and an eluent with a ratio of petroleum ether:ethyl acetate of 8:1 to 5:1, and the collected 5:1 When the eluent, the white solid product obtained by spinning is 3-(2-pyridylamino) ethyl propionate, and the productive rate is 65%;

[0034] The white s...

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Abstract

The invention discloses a preparation method of a 3-(2-pyridineamino)ethyl propionate. The method comprises the following steps: performing catalytic reaction by using 2-aminopyridine and ethyl acrylate as a raw material, and using a Bronsted acid loaded by silicagel as a catalyst in an inorganic solvent or an organic solvent and controlling temperature at 80-120 DEG C through oil bath heating, wherein the temperature of the obtained reaction mothersolution is 40-45 DEG.C, concentrating at the pressure of 0.09-0.1MPa at reduced pressure, performing the chromatography on the concentrated solution through a silicagel column or an aluminum oxide column to obtain 3-(2-pyridineamino)ethyl propionate. The preparation method of the 3-(2-pyridineamino)ethyl propionate has the characteristics of simple preparation method, convenience in operation, low production cost, and short reaction time; the used silicagel-loaded Bronsted acid catalyst can be recycled, and the product yield of the finally obtained 3-(2-pyridineamino)ethyl propionate achieves 50-76%.

Description

technical field [0001] The invention relates to a preparation method of ethyl 3-(2-pyridylamino)propionate. Background technique [0002] 3-(2-pyridylamino) ethyl propionate is one of the important intermediates in the synthesis of the direct thrombin inhibitor dabigatran etexilate (trade name: Pradaxa). Dabigatran etexilate is the first new class of oral anticoagulant drugs marketed 50 years after warfarin. Compared with warfarin, dabigatran etexilate has the characteristics of oral administration, rapid onset of action, no need for special drug monitoring, and less drug interaction. In vivo, in vitro tests and clinical studies have shown that it has good curative effect and pharmacokinetics. It has good clinical application prospect. Schematic diagram of the structure such as figure 1 The listing of dabigatran etexilate as shown is a major progress in the field of anticoagulant therapy and the prevention of potentially fatal thrombosis, which is of milestone significanc...

Claims

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Application Information

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IPC IPC(8): C07D213/74
CPCY02P20/584
Inventor 任玉杰王庆伟徐文倩
Owner SHANGHAI INST OF TECH
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