What Is 6-Boc-1,4,5,7-Tetrahydropyrazolo[3,4-c]pyridine-3-carboxylic Acid?

6-Boc-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridine-3-carboxylic acid (Aladdin SKU: B195180) is a bicyclic heterocyclic compound that fuses a pyrazole ring with a partially saturated piperidine ring. The nitrogen at position 6 of the piperidine portion is protected with a tert-butoxycarbonyl (Boc) group, while position 3 of the pyrazole carries a free carboxylic acid.

This dual-functionality—an acid handle for amide coupling and a Boc-protected amine for selective deprotection—makes the compound an attractive intermediate in the synthesis of pharmacologically relevant molecules. The fused ring system provides a rigid, three-dimensional scaffold that can improve binding selectivity in drug candidates compared to purely linear or monocyclic analogs.

Chemical Properties and Structural Features

The compound contains three key structural elements:

• Pyrazole ring (positions 1–3): A five-membered aromatic ring containing two adjacent nitrogen atoms. The C-3 carboxylic acid is available for further functionalization, including standard carbodiimide (EDC/DCC) or HATU-mediated amide bond formation.
• Partially saturated piperidine ring: The six-membered ring (positions 4–7) is saturated at positions 4, 5, and 7, conferring sp³ character and improved aqueous solubility compared to fully aromatic analogs.
• Boc protecting group: The N-Boc group on the piperidine nitrogen is stable under basic and neutral aqueous conditions but is readily cleaved under mildly acidic conditions (e.g., 20–50% trifluoroacetic acid in dichloromethane, or 4 M HCl in dioxane), releasing the free amine for further elaboration.

The presence of multiple nitrogen atoms in the scaffold makes this compound suitable for coordination chemistry and metal-chelating applications in addition to organic synthesis.

Handling, Storage, and Safety Considerations

Storage: Store the compound in a tightly sealed container in a cool, dry location away from direct light and moisture. Confirm the recommended temperature range (e.g., room temperature or 2–8 °C) on the specific lot's certificate of analysis (CoA) or product datasheet provided with the shipment.

Handling: Use standard personal protective equipment (PPE): laboratory coat, chemical-resistant gloves, and safety glasses. Work in a well-ventilated fume hood when weighing or dissolving the material. Although specific hazard classifications for this compound should be verified against the Safety Data Sheet (SDS), general precautions for fine organic powders apply, including avoiding inhalation of dust.

Solubility: The compound is expected to dissolve in polar aprotic solvents such as DMSO, DMF, and acetonitrile. Limited solubility may be observed in non-polar solvents. Verify exact solubility data on the product datasheet before use.

Stability: The Boc group is stable under neutral and basic conditions but will hydrolyze under acidic conditions. Avoid prolonged exposure to protic acids, strong Lewis acids, or humid environments that may trigger premature deprotection.

Applications in Medicinal Chemistry and Synthesis

The pyrazolopyridine scaffold found in this compound is a privileged structure in medicinal chemistry. Fused bicyclic systems incorporating pyrazole are found in numerous bioactive compounds and approved drugs, making this type of building block valuable for lead generation and library synthesis.

Typical synthetic applications include:

• Amide coupling: The C-3 carboxylic acid can be activated and coupled to primary or secondary amines using standard coupling reagents (e.g., EDC·HCl, HATU, DCC) to generate amide analogs for structure–activity relationship (SAR) studies.
• Boc deprotection and further functionalization: Removal of the Boc group under acidic conditions liberates the secondary amine, which can then be alkylated, acylated, sulfonylated, or reductively aminated to introduce structural diversity.
• Fragment-based drug discovery (FBDD): The compact, rigid bicyclic core is well-suited as a fragment hit or fragment-to-lead starting point.
• Peptidomimetic synthesis: The scaffold can serve as a non-natural amino acid surrogate to constrain peptide conformation.

Ordering, Quality, and Technical Support

SKU: B195180 — 6-Boc-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridine-3-carboxylic acid is available exclusively under this SKU at Aladdin Scientific.

Purity and Quality: Each lot is supplied with a certificate of analysis (CoA) that specifies purity (typically assessed by HPLC or NMR), appearance, and other quality parameters. Customers are encouraged to request the CoA before or upon receipt of the product.

Custom Quantities: If the standard pack size does not meet your project needs, contact Aladdin's customer service team to discuss custom quantities, bulk pricing, or custom synthesis options.

Technical Questions: For questions regarding specific reaction conditions, compatibility with downstream assays, or analytical characterization, please reach out to Aladdin's technical support team via the website or email. Our scientific team is available to assist with application-specific guidance.

Shipping: Products are shipped in accordance with applicable regulations for research chemicals. Confirm shipping conditions (ambient, cold chain) with customer service at the time of ordering to ensure compound integrity upon delivery.