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CS-W001157 4
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4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid

  • CAS No. 307313-03-7

  • Cat. No. CS-W022044
  • Purity≥97%
  • MDL No.MFCD09056814

*For research and further manufacturing use only, not for direct human use.

4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid|CS-W022044

Structure of 307313-03-7

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General Information

  • CAS No. 307313-03-7
  • Cat. No. CS-W022044
  • Purity ≥97%
  • MDL No. MFCD09056814
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O₂
  • Molecular Weight 166.18
  • Synonym(s) Pyrazolo[1,5-a]pyridine-2-carboxylicacid, 4,5,6,7-tetrahydro-
  • SMILES OC(=O)C1=NN2CCCCC2=C1

Description

This tetrahydropyrazolo[1,5-a]pyridine scaffold integrates a carboxylic acid functionality at the 2-position, enabling direct conjugation or derivatization in medicinal chemistry campaigns. The fused heterocyclic core exhibits enhanced metabolic stability and favorable solubility profiles under standard conditions, supporting its use in targeted drug discovery programs.

Application

4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid serves as a versatile heterocyclic building block in medicinal chemistry, offering a rigid, polar scaffold with defined hydrogen-bonding capacity. The carboxylic acid functionality enables direct coupling reactions, while the saturated pyrazole core provides metabolic stability and favorable pharmacokinetic properties. Its well-defined stereochemistry and bench stability facilitate reproducible synthesis and purification, making it suitable for parallel library generation and structure–activity relationship studies.

Synthesis

  • Route1

    References

    • SCHWARZ PHARMA AG Patent: WO2006/15737 A1, 2006 ; Location in patent: Page/Page column 49 ;
  • Route2

    References

    • EP1241170 A2, ; Page 59 ; EP 1241170 A2
  • Route3
    • Methyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate|CS-0136964
      307307-82-0
    • ~80%
    • In-stock
      4,5,6,7-Tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid|CS-W022044
      307313-03-7

    References

    • Duvey, Guillaume; Perry, Benjamin; Le Poul, Emmanuel; Poli, Sonia; Bonnet, Beatrice; Lambeng, Nathalie; Charvin, Delphine; Donovan-Rodrigues, Tansy; Haddouk, Hasnaa; Gagliardi, Stefania; Rocher, Jean-Philippe Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 16 p. 4523 - 4527

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   55.12
  • LogP   0.9176
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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