# US 12,180,195 B1 · 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile as an antimicrobial compound

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- Number: US 12,180,195 B1
- Document ID: US12180195B1
- Status: Granted
- Kind: B1
- Application number: 18/500,081
- Filed: 2023-11-01
- Granted: 2024-12-31
- Earliest claimed: 2023-11-01
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Lateef Ahmed; Mai Mostafa Khalaf Ali; Antar Ahmed Abdelhamid; Amer A. Amer
- Web page: https://patentgrep.com/patent/US12180195B1

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound useful as an antimicrobial agent. A method of making the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound includes adding a mixture of 3-acetyl-2H-1-benzopyran-2-one, 6-bromo-3-(3-(2,4-dichlorophenyl)prop-2-enoyl)-2H-1-benzopyran-2-one and malononitrile to a solution of a sodium alkoxide in an absolute alcohol with stirring to obtain a reaction mixture; irradiating the reaction mixture followed by cooling to room temperature to obtain a crude product; and purifying the crude product by filtering and recrystallization using the absolute alcohol.

## Claims

### Claim 1

A 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound having the formula I:
wherein R is methyl or ethyl.

### Claim 2 (depends on 1)

The 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 1, wherein R is methyl.

### Claim 3 (depends on 1)

The 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 1, wherein R is ethyl.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method of making the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 1, the method comprising:
adding a mixture of 3-acetyl-2H-1-benzopyran-2-one, 6-bromo-3-(3-(2,4-dichlorophenyl)prop-2-enoyl)-2H-1-benzopyran-2-one and malononitrile to a solution of a sodium alkoxide in an absolute alcohol with stirring to obtain a reaction mixture;
irradiating the reaction mixture followed by cooling to room temperature to obtain a crude product;
purifying the crude product by filtering and recrystallization using the absolute alcohol; and
obtaining the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound.

### Claim 6 (depends on 5)

The method of making the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 5, wherein the compound is 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-ethoxynicotinonitrile the sodium alkoxide is sodium ethoxide, and the absolute alcohol is absolute ethanol.

### Claim 7 (depends on 5)

The method of making the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 5, wherein the compound is 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-methoxynicotinonitrile, the sodium alkoxide is sodium methoxide, and the absolute alcohol is absolute methanol.

### Claim 8 (depends on 5)

The method of making the 6-(6-bromo-2-oxo-2H-chromen-3-yl)-4-(2,4-dichlorophenyl)-2-alkoxynicotinonitrile compound of claim 5, wherein the irradiating step is conducted in an MW oven and lasts for about 35 minutes to about 40 minutes.