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Synthesis process of OAB-14

A technology of OAB-14, 1.OAB-14, applied in the preparation of organic compounds, carbamic acid derivatives, urea derivatives, etc.

Active Publication Date: 2021-12-07
SHANDONG XINHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the presence of 60 times the volume to mass ratio of solvent in the improved process, no solid insoluble matter is adsorbed by activated carbon after hot filtration, indicating that no insoluble matter is generated

Method used

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  • Synthesis process of OAB-14
  • Synthesis process of OAB-14
  • Synthesis process of OAB-14

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]Add OAB-14-7 (21.44g), 200ml dichloromethane, anhydrous potassium carbonate (17.33g, 2.5eq.) into a 500ml four-neck flask, stir well, add phenyl chloroformate (20.1g, 2.5eq.), after dripping, the temperature was raised to reflux, and the temperature was kept at reflux for 5.5h.

[0077] Add 200ml of purified water, and cool to room temperature in an ice bath. Suction filtration, 200ml of purified water to wash the filter cake, and then 200ml of dichloromethane to wash the filter cake. The filter cake was beaten again with 200ml of dichloromethane for 1h. Suction filtration and drying yielded 21.47 g of white solid.

[0078] The HPLC detection content was 97.197%, and OAB-14-7 remained 1.731%, and the yield was 81.17%.

[0079] Add triethylamine (7.6g, 3eq.), ethylenediamine (9g, 6eq.) and 100ml tetrahydrofuran to a 250ml four-necked flask, stir evenly, and then add the phenyl ester prepared in the previous step in batches at room temperature solid (10 g), after the a...

Embodiment 2

[0082] Add OAB-14-7 (21.44g), 200ml dichloromethane, anhydrous potassium carbonate (20.80g, 3.0eq.) into a 500ml four-necked flask, stir evenly, add phenyl chloroformate (24.2g, 3.0eq.), after dripping, the temperature was raised to reflux, and the temperature was kept at reflux for 5h.

[0083] Add 200ml of purified water, and cool to room temperature in an ice bath. Suction filtration, 200ml of purified water to wash the filter cake, and then 200ml of dichloromethane to wash the filter cake. The filter cake was beaten again with 200ml of dichloromethane for 1h. Suction filtration and drying yielded 18.97 g of white solid.

[0084] The HPLC detection content was 95.83%, and OAB-14-7 remained 1.519%, and the yield was 70.71%.

[0085] Add triethylamine (5.07g, 2eq.), ethylenediamine (12g, 8eq.) and 100ml tetrahydrofuran into a 250ml four-necked flask, stir well, and then add the phenyl ester prepared in the previous step in batches at room temperature solid (10 g), after t...

Embodiment 3

[0088] Add OAB-14-7 (21.44g), 200ml dichloromethane, anhydrous potassium carbonate (24.26g, 3.5eq.) into a 500ml four-necked flask, stir well, add phenyl chloroformate (28.2g, 3.5eq.), after dripping, the temperature was raised to reflux, and the temperature was kept at reflux for 4.5h.

[0089] Add 200ml of purified water, and cool to room temperature in an ice bath. Suction filtration, 200ml of purified water to wash the filter cake, and then 200ml of dichloromethane to wash the filter cake. The filter cake was beaten again with 200ml of dichloromethane for 1h. Suction filtration and drying yielded 21.63 g of white solid.

[0090] The HPLC detection content was 96.466%, and OAB-14-7 remained 2.273%, and the yield was 81.16%.

[0091] Add triethylamine (8.87g, 3.5eq.), ethylenediamine (15g, 10eq.) and 100ml tetrahydrofuran into a 250ml four-necked flask respectively, stir evenly, and then add the phenyl ester prepared in the previous step in batches at room temperature Th...

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Abstract

The invention provides a synthesis process of OAB-14. The synthesis process comprises the steps of (1) adding anhydrous potassium carbonate and dichloromethane into an intermediate 7 of OAB-14, uniformly stirring, dropwise adding phenyl chloroformate, heating to reflux, and keeping the temperature and refluxing until the reaction is finished; (2) stopping heating, adding purified water, cooling to room temperature in an ice bath, centrifuging, washing the solid with dichloromethane, pulping with dichloromethane, centrifuging, and drying to obtain a phenyl ester intermediate; and (3) mixing triethylamine, ethidene diamine and tetrahydrofuran, adding the phenyl ester intermediate prepared in the step (2) in batches at room temperature, heating to reflux, determining a reaction endpoint by TLC, cooling, cooling to the temperature of 5-10 DEG C in the ice bath, cooling and crystallizing for 1 hour, centrifuging, washing with dichloromethane, and drying to obtain the OAB-14.

Description

technical field [0001] The invention relates to the improvement of OAB-14 synthesis process and belongs to the technical field of medicine synthesis. Background technique [0002] OAB-14, the chemical name is 4-(3-(2-aminoethyl)ureido)-N-(1,1,4,4,5,5,8,8-octamethyl-1,2, 3,4,5,6,7,8-Octahydroanthracene-9-yl)benzamide is a class of new drug under research by our company, which is used for the treatment of Alzheimer's disease. The pathogenesis of Alzheimer's disease is very complicated. There are many theories at present, among which the cholinergic theory, Aβ amyloid plaque theory, Tau protein hyperphosphorylation theory, inflammation theory, oxidative stress theory, etc. are generally accepted. These theories have some corresponding drugs under development, currently mainly focusing on Aβ amyloid, Tau protein and other targets, but γ-secretase inhibitors that reduce the production of Aβ amyloid have failed in phase III clinical trials one after another. The failure of the A...

Claims

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Application Information

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IPC IPC(8): C07C273/18C07C275/42
CPCC07C273/1836C07C269/04C07C275/42C07C271/58Y02E60/10
Inventor 郑忠辉张富强吴辉常森曹丽丽易晓清
Owner SHANDONG XINHUA PHARMA CO LTD
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