2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid
[CAS# 1363380-86-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid
• Synonyms: 2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-6-carboxylic acid
• Molecular Formula: C₁₃H₁₈N₂O₄
• Molecular Weight: 266.29
• CAS Registry Number: 1363380-86-2
• EC Number: 876-586-4
• SMILES: CC(C)(C)OC(=O)N1CCN2C(=CC=C2C(=O)O)C1

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H320
• Safety Statements: P202-P261-P280

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid is a synthetic compound characterized by its unique bicyclic structure, which combines features of both pyrrole and pyrazine. This compound is part of a broader class of heterocyclic compounds that are of significant interest in medicinal chemistry due to their diverse biological activities. The molecular formula of 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid is C12H14N2O3, and it contains a tert-butyloxycarbonyl (Boc) protecting group that plays a crucial role in synthetic applications.

The discovery of 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid stems from ongoing research aimed at developing new compounds for various therapeutic applications. This compound was identified as part of efforts to explore the potential of bicyclic scaffolds in drug design. The presence of both the pyrrole and pyrazine rings in the structure contributes to its chemical stability and reactivity, making it a suitable candidate for further modification and exploration.

One of the primary applications of 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid is its role as an intermediate in the synthesis of bioactive molecules. The Boc protecting group allows for the selective functionalization of the carboxylic acid moiety, facilitating the introduction of various substituents that can enhance the compound's pharmacological properties. This versatility has made it a valuable building block in the synthesis of novel pharmaceuticals targeting a range of conditions, including cancer, inflammation, and neurological disorders.

Moreover, the compound has been investigated for its potential as a ligand in drug development. Studies have indicated that derivatives of 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid may interact with specific biological targets, including receptors and enzymes, which are pivotal in regulating various physiological processes. This aspect has prompted research into its structure-activity relationship (SAR), aiming to optimize the compound's efficacy and selectivity for therapeutic use.

In addition to its medicinal applications, 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid has potential uses in material science and organic synthesis. The unique bicyclic structure allows for the development of novel polymers and materials with tailored properties. Its ability to undergo various chemical transformations can be leveraged in the synthesis of complex organic molecules, expanding its applicability in synthetic chemistry.

In summary, 2-Boc-3,4-dihydro-1H-pyrrolo[1,2-A]pyrazine-6-carboxylic acid is a significant compound in the realm of medicinal chemistry and organic synthesis. Its structural features, combined with the versatility afforded by the Boc protecting group, enable its use in the development of novel therapeutics and materials. Ongoing research continues to explore the potential applications of this compound, highlighting its importance in drug discovery and synthetic methodology.

References

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