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Method for preparing benvitimod from (E)-3,5-dimethoxy-4-isopropyl stilbene

A technology of isopropyl stilbene and dimethoxy, which is applied in the field of drug synthesis, can solve the problem of high reaction temperature, achieve the effects of lowering reaction temperature, easy operation, and improving reaction yield and purity

Inactive Publication Date: 2013-08-28
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the protecting group is methyl, the microwave power is 20W, the temperature is controlled at 200-220°C, the reaction time is 30min, and the yield is 93%, but the above reaction method has a higher reaction temperature

Method used

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  • Method for preparing benvitimod from (E)-3,5-dimethoxy-4-isopropyl stilbene
  • Method for preparing benvitimod from (E)-3,5-dimethoxy-4-isopropyl stilbene
  • Method for preparing benvitimod from (E)-3,5-dimethoxy-4-isopropyl stilbene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment １-5

[0062] Example 1-5 Method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene (using aluminum trichloride as demethylation reagent, using single power microwave )

[0063] Examples 1-5 are respectively a method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene. They all use a combination of demethylation reagent and microwave Method, the demethylation reagent is aluminum trichloride, the microwave method is 80-90°C, 400-500W microwave reaction for 10-20min.

[0064] Refer to Table 1, the specific preparation method is as follows:

[0065] Dissolve 0.3g (E)-3,5-dimethoxy-4-isopropyl stilbene in 15mL of toluene, place it in a low temperature tank and stir; cool down to the temperature ① that is -2~2℃ (see table 1), slowly add 0.81mL N,N-dimethylaniline, of which (E)-3,5-dimethoxy-4-isopropyl stilbene and N,N-dimethylaniline The reaction molar ratio is 1:6; then 0.85g aluminum trichloride is added in batches, among which (E)-3,5-dimethoxy-4-isopropy...

Embodiment 6-10

[0067] Example 6-10 Method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene (using aluminum trichloride as demethylation reagent, using microwaves of different powers) Multiple cycles)

[0068] Examples 6-10 are respectively a method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene, and they all use demethylation reagent combined with microwave The method, the demethylation reagent is aluminum trichloride, and the microwave method is a method of multiple cycles of irradiation with different powers, and the first microwave power is P 1 =500~600W, microwave irradiation time is t 1 =1~2min; the second microwave power is P 2 =400~500W, microwave irradiation time is t 2 =2~3min; the third microwave power is P 3 =200~400W, microwave irradiation time is t 3 =2~3min, one cycle, 2-4 cycles.

[0069] Refer to Table 2, the specific preparation method is as follows:

[0070] Dissolve 0.3g (E)-3,5-dimethoxy-4-isopropyl stilbene in 15mL of toluene, place it ...

Embodiment 11-15

[0072] Example 11-15 Method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene (using pyridine hydrochloride as demethylation reagent, using single power microwave )

[0073] Examples 11-15 are respectively a method for preparing phenenmod from (E)-3,5-dimethoxy-4-isopropyl stilbene, all of which use a combination of demethylation reagent and microwave Method, the demethylation reagent is pyridine hydrochloride, wherein the reaction mass ratio of (E)-3,5-dimethoxy-4-isopropyl stilbene to pyridine hydrochloride is 1:5, microwave The method is 140~150℃, 400~500W microwave reaction for 10~20min.

[0074] Refer to Table 3, the specific preparation method is as follows:

[0075] Mix 0.3g (E)-3,5-dimethoxy-4-isopropyl stilbene with 1.5g pyridine hydrochloride, place it in a microwave reactor, and heat to temperature ① that is 140~150℃, Reaction under 400~500W microwave for 10~20min. After the reaction is complete, add 20mL dilute hydrochloric acid, adjust to pH 3~5, ex...

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Abstract

The invention discloses a method for preparing benvitimod from (E)-3,5-dimethoxy-4-isopropyl stilbene. According to the method, a demethylation reagent is combined with the microwave technique, and a method of the combined action of the demethylation reagent with single-power microwaves or multiple-cycle microwaves with different powers is adopted, so as to achieve the effects of reducing the reaction temperature, shortening the reaction time, reducing by-products and improving the reaction yield and purity. The method is suitable for preparing benvitimod which can be further applied to treating diseases such as inflammation, dermatosis, psoriasis, tumors and the like.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a preparation method of styrene moder, specifically a method for preparing styrene moder from (E)-3,5-dimethoxy-4-isopropylstilbene. moral method. technical field [0002] The invention belongs to the field of drug synthesis, and relates to a preparation method of styrene moder, specifically a method for preparing styrene moder from (E)-3,5-dimethoxy-4-isopropylstilbene. moral method. Background technique [0003] Benzene modad, chemical name ( E )-3,5-dihydroxy-4-isopropyl stilbene, a stilbene compound, is a derivative of symbiotic bacterial extracts with large intestine parasitic nematodes. Studies have shown that ( E )-3,5-dihydroxy-4-isopropyl stilbene has physiological activity on neutrophil-related diseases or physiological disorders related to protein-activating enzymes, including inflammation, skin diseases, psoriasis, tumors, etc. ( E )-3,5-dihydroxy-4-isopropyl st...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055
Inventor 张越杜曼
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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