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Method for preparing benzamide compound and its intermediate

A technology of benzamide and compound, applied in the field of preparation of benzamide compound, can solve the problems of low safety, complicated operation, low yield and the like

Active Publication Date: 2016-10-05
CHEMVON BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The technical problem to be solved by the present invention is to provide a kind of preparation method of benzamide compound and its intermediate in order to overcome defects such as low yield, cumbersome operation, low safety and environmental pollution of the existing preparation method of benzamide compound. body, the method has high yield, simple operation, high safety, clean and environmental protection, and is suitable for industrial production

Method used

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  • Method for preparing benzamide compound and its intermediate
  • Method for preparing benzamide compound and its intermediate
  • Method for preparing benzamide compound and its intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0107] The preparation of embodiment 1 benzamide compound 3

[0108] In a 3L three-necked flask, add compound 1 (200g, 0.86mol), compound 2 (133g, 1.29mol), cuprous chloride (16.8g, 0.17mol), compound A (20.8g, 0.1mol) and potassium carbonate solid (303.6 g, 2.2 mol), then add 1 liter of DMF and 20 ml of distilled water, and replace nitrogen three times. Turn on the heating and raise the temperature to 115 degrees, TLC detection, after 10 hours, the raw materials completely disappeared. Stop responding. Let cool to room temperature.

[0109] Filter to remove solid insolubles, wash the filter residue with a little DMF, combine the filtrates, evaporate to dryness under reduced pressure, add 400ml of water to completely dissolve the system, and extract twice with 400ml of isopropyl acetate to remove organic impurities in the raffinate. The water phase was stirred, and a saturated citric acid solution was added dropwise therein to adjust the pH of the reaction system to 4-5, an...

Embodiment 2

[0110] The preparation of embodiment 2 benzamide compound 3

[0111] In a 3L three-necked flask, add compound 1 (200g, 0.86mol), compound 2 (133g, 1.29mol), cuprous chloride (16.8g, 0.17mol), compound A (20.8g, 0.1mol) and potassium carbonate Solid (303.6 g, 2.2 mol), then 1 liter of DMF was added, and nitrogen was replaced three times. Turn on the heating and raise the temperature to 115 degrees, TLC detection, after 15 hours, the raw materials completely disappeared. Stop responding. Let cool to room temperature.

[0112] Filter to remove solid insolubles, wash the filter residue with a little DMF, combine the filtrates, evaporate to dryness under reduced pressure, add 400ml of water to completely dissolve the system, and extract twice with 400ml of isopropyl acetate to remove organic impurities in the raffinate. The water phase was stirred, and a saturated citric acid solution was added dropwise therein to adjust the pH of the reaction system to 4-5, and then cooled to b...

Embodiment 3

[0113] The preparation of embodiment 3 benzamide compound 4

[0114] Add benzamide compound 3 (15g, 59mmol) and 75 grams of methanol in a 250ml three-necked flask, add thionyl chloride (45g, 378mmol) dropwise thereto under stirring, add, reflux, and at this temperature Stirring was continued for 6 hours, and the raw material disappeared completely as detected by TLC.

[0115] Concentrate under reduced pressure, distill off the solvent, and then slowly pour the reaction solution into saturated aqueous sodium bicarbonate solution to adjust the pH of the system to 7-8. At this time, a large amount of white solid is precipitated. After filtering, the filter cake was beaten with 80 ml of water for 30 minutes, and filtered again to obtain a white solid, which was vacuum-dried at 60 degrees to constant weight to obtain 15 g, with a yield of 90% and a purity of 98.5% by HPLC.

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Abstract

The invention discloses a method for preparing a benzamide compound and its intermediate. The method comprises the following steps: under protection by protective gas, in a polar aprotic solvent, under existence of a catalyst shown as a formula A, and cuprous halide and inorganic base, a compound 1 and a compound 2 are subjected to a coupling reaction to obtain the benzamide compound. The method has the advantages of high yield, simple operation, high security, cleaning, and environmental protection, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a benzamide compound and an intermediate thereof. Background technique [0002] At present, it has been approved by the US FDA for the treatment of metastatic castration-resistant prostate cancer after docetaxel treatment, and research data have shown that enzalutamide is also effective in patients who have not been treated with docetaxel. The researchers found that enzalutamide significantly delayed the start of chemotherapy and significantly optimized prostate-specific antigen (PSA) response rates, time to PSA progression, objective soft tissue response rates, and time to first bone-related events. At 26 months of follow-up, no median survival was found in the enzalutamide-treated group and 31 months in the placebo group. In addition, the quality of life response rate was nearly 40% in the enzalutamide-treated group, compared with 22.9% in the placebo group. Enzalutamide significantly improved patien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/30C07C231/12C07D233/86
Inventor 王东王方道蔡茂军王猛周杰
Owner CHEMVON BIOTECH CO LTD
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