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CS-W001157 4
Total: USD 88.00

2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid

  • CAS No. 21801-79-6

  • Cat. No. CS-0038336
  • Purity≥95%
  • MDL No.MFCD00244615

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

2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid|CS-0038336

Structure of 21801-79-6

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General Information

  • CAS No. 21801-79-6
  • Cat. No. CS-0038336
  • Purity ≥95%
  • MDL No. MFCD00244615
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O₂
  • Molecular Weight None
  • Synonym(s) 2-methylimidazo[1,2-a]pyridine-3-carboxylate
  • SMILES O=C(C1=C(C)N=C2C=CC=CN21)O

Description

This heterocyclic carboxylic acid features a fused imidazo[1,2-a]pyridine core with a methyl substituent at the 2-position, enhancing electronic delocalization and solubility. The carboxylic acid group enables direct coupling in peptide synthesis or metal coordination. Designed for medicinal chemistry applications, it offers improved metabolic stability and targeted receptor binding compared to non-substituted analogs.

Application

2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry and catalytic system development. Its fused tricyclic core provides enhanced rigidity and defined spatial orientation, enabling precise molecular positioning in target-directed synthesis. The carboxylic acid functionality facilitates direct amidation, esterification, or metal coordination, while the methyl group enhances metabolic stability and modulates lipophilicity. This compound exhibits good bench stability and compatibility with standard purification techniques, making it suitable for iterative synthetic workflows and API intermediate construction.

Synthesis

  • Route1
    • null|null
      504-29-0
    • In-stock
      Ethyl 2-chloroacetoacetate|CS-W018512
      609-15-4
    • ~45%
    • In-stock
      2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid|CS-0038336
      21801-79-6

    References

    • MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan Patent: WO2010/90716 A1, 2010 ; Location in patent: Page/Page column 321 ;
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    References

    • Kuemmerle, Arthur E.; Schmitt, Martine; Cardozo, Suzana V. S.; Lugnier, Claire; Villa, Pascal; Lopes, Alexandra B.; Romeiro, Nelilma C.; Justiniano, Helene; Martins, Marco A.; Fraga, Carlos A. M.; Bourguignon, Jean-Jacques; Barreiro, Eliezer J. Journal of Medicinal Chemistry, 2012 , vol. 55, # 17 p. 7525 - 7545
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 76, p. 1845

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   54.6
  • LogP   1.34092
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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