7-Amino-furo[2,3-b]pyrazine-6-carboxylic Acid Ethyl Ester: Overview
7-Amino-furo[2,3-b]pyrazine-6-carboxylic Acid Ethyl Ester: Overview
7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester is a bicyclic heteroaromatic building block featuring a fused furan–pyrazine core with a free amino group and an ethyl ester functionality, making it a versatile intermediate for medicinal chemistry and drug-discovery research.
- Product Name
- 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester
- SKU
- A182346
- Core Scaffold
- Furo[2,3-b]pyrazine bicyclic system
- Key Functional Groups
- Primary amino group (–NH₂) and ethyl ester (–CO₂Et)
- Primary Application
- Medicinal chemistry intermediate and heterocyclic building block
- Supplier
- Aladdin Scientific
Chemical Structure and Key Features
7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester belongs to the furo[2,3-b]pyrazine family of bicyclic heteroaromatic compounds. Its scaffold consists of a furan ring fused to a pyrazine ring in a [2,3-b] connectivity pattern, creating a planar, electron-deficient aromatic system. Two strategically positioned functional groups—a primary amino group at the 7-position and an ethyl ester at the 6-position—render this molecule highly amenable to further chemical elaboration.
The electron-withdrawing pyrazine nitrogen atoms lower the overall electron density of the ring system, enhancing the electrophilicity of certain ring positions and facilitating nucleophilic aromatic substitution reactions under appropriate conditions. Simultaneously, the free –NH₂ group acts as a handle for acylation, sulfonylation, reductive amination, and cyclization reactions, while the ethyl ester can be hydrolyzed, reduced, or used in condensation reactions to introduce additional diversity.
Applications in Medicinal Chemistry and Drug Discovery
Fused heteroaromatic scaffolds incorporating pyrazine motifs are widely represented in bioactive molecules and approved pharmaceuticals. The furo[2,3-b]pyrazine core found in 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester is of interest as a bioisosteric replacement for other bicyclic heteroaromatics such as furopyridines or thienopyrazines, enabling medicinal chemists to modulate physicochemical properties including lipophilicity, solubility, and metabolic stability.
The dual functionality of this building block—a nucleophilic amine and an electrophilic ester—supports rapid construction of analogue libraries through parallel synthesis. The compound may serve as a precursor to fused tricyclic systems via intramolecular cyclization, as well as to amide and urea derivatives relevant to kinase inhibitor programs, antiviral agent development, and other therapeutic areas where electron-deficient heteroaromatics demonstrate favorable target engagement.
Researchers in fragment-based drug discovery (FBDD) also value compact, functionalized bicyclic heterocycles such as this compound because they present multiple vectors for elaboration within a low-molecular-weight framework, supporting efficient exploration of chemical space.
Handling, Storage, and Safety Considerations
As with most fine chemical research reagents, 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester should be handled under standard laboratory safety protocols. Researchers are advised to wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat when weighing or transferring the compound. Operations that may generate dust or aerosols should be performed in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container, protected from light, heat, and moisture to prevent decomposition or hydrolysis of the ethyl ester functionality. Storage at low temperature (typically 2–8 °C or as specified on the product label) in a dry environment is recommended. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard classifications, first-aid measures, and disposal guidance before use.
As a general best practice, stock solutions should be prepared in dry, high-purity solvents such as DMSO or DMF when aqueous instability is anticipated, and aliquots should be stored to minimize freeze-thaw cycles.
Ordering and Quality Assurance
7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester is available from Aladdin Scientific under SKU A182346. Aladdin Scientific is committed to supplying research-grade reagents that meet stringent purity specifications, supporting reproducible experimental outcomes. Analytical data such as NMR spectra, HPLC purity traces, and mass spectrometry confirmation are typically provided or available upon request to help researchers verify compound identity and purity prior to use.
For bulk quantities, custom packaging, or questions regarding technical specifications, customers are encouraged to contact Aladdin Scientific's technical support team. Volume discounts and institutional pricing may be available; please refer to the current product listing or contact your regional Aladdin Scientific representative for up-to-date pricing and availability information.
Frequently asked questions
What is 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester used for?
This compound is primarily used as a heterocyclic building block in medicinal chemistry and drug-discovery research. Its free amino and ethyl ester groups provide multiple sites for chemical elaboration, enabling the synthesis of diverse analogue libraries, fused tricyclic scaffolds, and biologically relevant derivatives such as amides, ureas, and cyclized products.
How should I store 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester to maintain its stability?
The compound should be stored in a tightly sealed container at low temperature (typically 2–8 °C), protected from light, heat, and moisture. For solution-phase storage, dry aprotic solvents such as DMSO are recommended, and repeated freeze-thaw cycles should be avoided by storing aliquots separately.
What is the SKU for this product at Aladdin Scientific?
7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester is listed under SKU A182346 at Aladdin Scientific. Researchers can use this SKU to place orders directly or request a quotation from the Aladdin Scientific sales team.
What solvents are suitable for dissolving this compound?
Dry polar aprotic solvents such as DMSO and DMF are generally suitable for dissolving heteroaromatic building blocks of this type. Solubility in aqueous systems may be limited due to the lipophilic bicyclic core; researchers should test solubility empirically and consult the SDS for guidance.
Can this compound be used in aqueous reaction conditions?
Aqueous compatibility depends on the specific reaction conditions, pH, and temperature. The ethyl ester group is susceptible to hydrolysis under strongly acidic or basic aqueous conditions, which should be considered when designing reaction protocols. Pre-dissolution in a water-miscible organic solvent prior to aqueous dilution may improve handling.
References
- Comprehensive Heterocyclic Chemistry series (Elsevier) — general reference for furopyrazine ring systems and their reactivity.
- Kappe, C. O.; Stadler, A.; Dallinger, D. Microwaves in Organic and Medicinal Chemistry, 2nd ed.; Wiley-VCH, 2012 — general reference for heterocyclic building block elaboration strategies.
- Aladdin Scientific product page for SKU A182346 — 7-Amino-furo[2,3-b]pyrazine-6-carboxylic acid ethyl ester.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证(带存储)