6-aminouracil cassic acid ester with antibacterial activity and a method of preparing the same

Patent metadata

Field	Value
Publication number	US-10941120-B1
Application number	US-202016909862-A
Country	US
Kind code	B1
Filing date	Jun 23, 2020
Priority date	Jun 23, 2020
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

A compound having the formula (I):

is disclosed. A method of preparing the compound of formula (I) is also disclosed.

First claim

What is claimed is:

1. A compound of the following formula (I):

2. A method of preparing the compound of formula (I) of claim 1 , comprising: reacting a compound of formula (II) with a compound of formula (III) to obtain the compound of formula (I):

3. The method of claim 2 , wherein the reaction of the compound of formula (II) with the compound of formula (III) comprises the following steps:
placing the compound of formula (II) and the compound of formula (III), in a molar ratio of 1:1 to 1:1.3, in a reactor;
adding an organic solvent and a catalytic amount of EDC under nitrogen atmosphere to obtain a reaction mixture; and
heating the reaction mixture at 50-80° C. for 4-8 hours;
concentrating the reaction mixture and extracting the reaction mixture with ethyl acetate to obtain a crude product; and
purifying the crude product on a silica gel fresh chromatography column with petroleum ether and ethyl acetate as an eluent to obtain the compound of formula (I).

4. The method of claim 3 , wherein the organic solvent is toluene, tetrahydrofuran or acetonitrile.

5. The method of claim 4 , wherein the organic solvent is acetonitrile.

6. The method of claim 3 , wherein the molar ratio of the compound of formula (II) and the compound of formula (III) is 1:1.1.

7. The method of claim 3 , wherein the reaction mixture is heated at 70° C.

8. The method of claim 3 , wherein the reaction mixture is heated for 6 hours.

9. The method of claim 3 , wherein the eluent is petroleum ether:ethyl acetate=3:10.

10. The method of claim 2 , wherein the reaction of the compound of formula (II) with the compound of formula (III) comprises the following steps:
placing the compound of formula (II), a catalyst, and an ionic liquid in a reactor under nitrogen atmosphere, the catalyst being 12-molybdosilicic acid hydrate (H 6 Mo 12 O 41 Si);
adding the compound of formula (III) to the reactor to form a reaction mixture;
heating the reaction mixture at 25-50° C. for 5-10 hours;
placing the reaction mixture in a separating funnel to separate a crude product;
purifying the crude product by recrystallization in methanol to obtain the compound of formula (I); and
recycling the ionic liquid.

11. The method of claim 10 , wherein the ionic liquid is 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF 4 ]).

12. The method of claim 10 , wherein the compound of formula (II) and the compound (III) have a molar ratio of 1:1 to 1:1.3.

13. The method of claim 12 , wherein the molar ratio of the compound of formula (II) and the compound of formula (III) is 1:1.1.

14. The method of claim 10 , wherein the reaction mixture is heated at 30° C.

15. The method of claim 10 , wherein the reaction mixture is heated for 8 hours.

Assignees

• Li Han
• Hui nan
• Liang Chengyuan
• Ju Xingke
• Qiao Guaiping
• Li Juan
• He Yuanyuan
• Tian Bin
• Wang Yongbo
• Xu Jingwen
• Qi Liang
• Yang Dan
• Zhao Qianqian
• Li Yanjun
• Zeng Qiao
• Mao Gennian
• Wang Limei
• Univ Shaanxi Science & Tech

Inventors

• Li Han
• Hui nan
• Liang Chengyuan
• Ju Xingke
• Qiao Guaiping
• Li Juan
• He Yuanyuan
• Tian Bin
• Wang Yongbo
• Xu Jingwen
• Qi Liang
• Yang Dan
• Zhao Qianqian
• Li Yanjun
• Zeng Qiao
• Mao Gennian
• Wang Limei

Classifications

• C07D239/545 Primary

  with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms · CPC title