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

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Pyrroles
• Name: N-[5-[(4-Methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamic acid ethyl ester
• Synonyms: ethyl N-[5-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyrazin-2-yl]carbamate
• Molecular Formula: C₁₆H₁₆N₄O₄S
• Molecular Weight: 360.39
• CAS Registry Number: 1869118-24-0
• EC Number: 943-940-5
• SMILES: CCOC(=O)NC1=CN=C2C(=N1)C=CN2S(=O)(=O)C3=CC=C(C=C3)C

Properties

• Solubility: Insoluble (6.5E^-3 g/L) (25 °C), Calc.^*
• Density: 1.43±0.1 g/cm³ (20 °C 760 torr), Calc.^*
• Index of Refraction: 1.664, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

N-[5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamate is an innovative compound with great significance in both organic and medicinal chemistry. The compound has a pyrrolo[2,3-b]pyrazine core with a sulfonyl group attached to the 4-methylphenyl moiety and a carbamate bonded to it. The combination of these functional groups contributes to the unique reactivity and biological activity of the molecule. The sulfonyl group is particularly noteworthy for its role in modulating chemical reactivity and interaction with biological targets.

In medicinal chemistry, N-[5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamate is being studied for its potential as a therapeutic agent. The structure of the compound suggests that it can interact with specific enzymes or receptors, making it a candidate for the development of treatments for various diseases. Its sulfonyl and carbamate groups can enhance binding affinity and selectivity to biological targets, which is critical for drug development.

In addition to its medicinal uses, this compound has several other applications, as it can serve as a key intermediate in the synthesis of complex molecules due to its reactive functional groups. Its unique chemical structure could potentially be used to create advanced materials, including polymers or coatings with specific properties. The molecule's functional groups could be used in bioconjugation techniques to facilitate the attachment of tags or therapeutic agents to biomolecules.

Ethyl N-[5-[(4-methylphenyl)sulfonyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamate represents a significant advancement in chemical research. From potential drug development to materials science, its wide range of applications highlights its versatility and promise. As research continues, this compound could play an important role in advancing pharmaceutical and synthetic chemistry.

References

2022. Synthesis of Upadacitinib. Synfacts.
DOI: 10.1055/s-0041-1738394

2020. Upadacitinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-21-0010