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Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate

  • CAS No. 158980-21-3

  • Cat. No. CS-0006083
  • Purity≥95%
  • MDL No.MFCD05864804

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

Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate|CS-0006083

Structure of 158980-21-3

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General Information

  • CAS No. 158980-21-3
  • Cat. No. CS-0006083
  • Purity ≥95%
  • MDL No. MFCD05864804
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₁N₃O₂
  • Molecular Weight 205.21
  • Synonym(s) Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-amino-, ethyl ester (9CI)
  • SMILES O=C(C1=CN2C=C(N)C=CC2=N1)OCC

Description

Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate features a fused heterocyclic core with a pendant amino group and ester functionality. This electron-rich scaffold integrates readily into medicinal chemistry campaigns, serving as a key intermediate for imidazopyridine-based bioactive molecules. The compound exhibits bench-stable handling characteristics and compatibility with diverse synthetic transformations.

Application

Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate serves as a versatile building block for the synthesis of biologically relevant heterocyclic scaffolds. The amino group enables direct functionalization via acylation, alkylation, or coupling reactions, while the ester moiety supports further derivatization or hydrolysis to the carboxylic acid. Its stability under standard bench conditions and compatibility with common coupling protocols make it well-suited for medicinal chemistry campaigns targeting kinase inhibitors and other nitrogen-rich pharmacophores.

Synthesis

  • Route1

    References

    • Blache, Yves; Gueiffier, Alain; Chavignon, Olivier; Viols, Henry; Teulade, Jean Claude; Chapat, Jean Pierre Heterocycles, 1994 , vol. 38, # 7 p. 1527 - 1532

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

Quality Control

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Computational Chemistry Data

  • TPSA   69.62
  • LogP   1.0932
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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