Product Introduction of N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester (CAS 1869118-24-0)

N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester, with the CAS number 1869118-24-0, is a chemical compound that has attracted significant attention in the field of organic chemistry and pharmaceutical research. This product is known for its unique chemical structure and potential biological activities.

Chemical Properties

The molecular formula of N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester is \(C_{16}H_{16}N_{4}O_{4}S\). It has a specific molecular weight that can be calculated based on the atomic masses of its constituent elements. The compound contains a pyrrolopyrazine core structure, which is often associated with interesting electronic and steric properties. The presence of the sulfonyl group and the carbamic acid ethyl ester moiety further contributes to its chemical reactivity and potential biological interactions.

The solubility of N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester in different solvents is an important property. It may have limited solubility in water but could be more soluble in organic solvents such as dimethyl sulfoxide (DMSO), ethanol, or acetonitrile. This solubility behavior is crucial for its use in various experimental and industrial applications.

The stability of the compound under different conditions, such as temperature, pH, and light exposure, also needs to be considered. It is important to store N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester in a cool, dry place away from direct sunlight to maintain its chemical integrity.

Synthesis and Preparation

The synthesis of N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester typically involves a multi – step process. One possible synthetic route starts with the preparation of the pyrrolopyrazine intermediate. This can be achieved through a series of condensation and cyclization reactions.

First, appropriate starting materials, such as pyrrole and pyrazine derivatives, are selected. These starting materials are reacted under specific reaction conditions, which may include the use of catalysts, solvents, and specific temperatures. For example, a base – catalyzed condensation reaction can be used to form the initial carbon – carbon and carbon – nitrogen bonds in the pyrrolopyrazine ring system.

After the formation of the pyrrolopyrazine core, the sulfonyl group is introduced. This is usually done by reacting the pyrrolopyrazine intermediate with a suitable sulfonylating agent, such as p – toluenesulfonyl chloride, in the presence of a base. The base helps to deprotonate the pyrrolopyrazine and facilitate the reaction with the sulfonylating agent.

Finally, the carbamic acid ethyl ester group is added. This can be accomplished by reacting the sulfonylated pyrrolopyrazine with an appropriate carbamoylating agent, such as ethyl chloroformate, in the presence of a base. The reaction conditions need to be carefully controlled to ensure high yield and purity of the final product.

It is important to note that the synthesis process may require purification steps, such as column chromatography or recrystallization, to obtain the pure N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester.

Biological Activities and Potential Applications

Pharmaceutical Research

In pharmaceutical research, N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester has shown potential as a lead compound for the development of new drugs. Its unique chemical structure may allow it to interact with specific biological targets, such as enzymes or receptors.

For example, it may act as an inhibitor of certain kinases, which are enzymes involved in cell signaling pathways. By inhibiting kinases, the compound could potentially disrupt abnormal cell growth and proliferation, making it a candidate for the treatment of cancer and other diseases related to abnormal cell signaling.

It may also have antibacterial or antifungal activities. The compound’s ability to penetrate the cell membranes of bacteria or fungi and interact with their intracellular targets could lead to the development of new antibiotics or antifungal agents.

Material Science

In material science, N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester could be used as a building block for the synthesis of new polymers or materials with specific properties. Its unique chemical structure may contribute to the formation of polymers with interesting electronic or optical properties.

For example, the compound could be incorporated into a polymer backbone to enhance its conductivity or fluorescence properties. This could have applications in the development of organic electronic devices, such as organic light – emitting diodes (OLEDs) or organic solar cells.

Agrochemicals

In the field of agrochemicals, N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester may have potential as a pesticide or herbicide. Its ability to interact with specific biological targets in pests or weeds could lead to the development of more effective and environmentally friendly agrochemicals.

For example, it could act as an inhibitor of key enzymes in pests, disrupting their metabolic processes and leading to their death. Or it could interfere with the growth and development of weeds, providing a new approach for weed control.

Safety and Handling

When handling N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester, appropriate safety precautions should be taken. The compound may be toxic if ingested, inhaled, or absorbed through the skin. Therefore, it is important to wear appropriate personal protective equipment, such as gloves, goggles, and a lab coat.

It should be handled in a well – ventilated area to avoid inhalation of dust or vapors. In case of contact with the skin or eyes, immediately rinse with plenty of water and seek medical attention if necessary. Spills should be cleaned up carefully using appropriate absorbent materials, and the waste should be disposed of in accordance with local regulations.

Quality Control

To ensure the quality and purity of N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester, various analytical techniques are used. High – performance liquid chromatography (HPLC) is commonly used to determine the purity of the compound. Nuclear magnetic resonance (NMR) spectroscopy can be used to confirm the chemical structure of the product.

Elemental analysis can also be performed to determine the elemental composition of the compound and ensure that it matches the expected values. Additionally, melting point determination can be used as a simple method to assess the purity and identity of the product.

References

• Author, A. (Year). Title of the research. Journal Name, Volume(Issue), Page numbers.
• Author, B., & Author, C. (Year). Another research title. Book Name, Publisher, Page numbers.

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