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5-Morpholinopyridin-2-amine

  • CAS No. 571189-78-1

  • Cat. No. CS-0034814
  • Purity≥96%
  • MDL No.MFCD09388785

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

5-Morpholinopyridin-2-amine|CS-0034814

Structure of 571189-78-1

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General Information

  • CAS No. 571189-78-1
  • Cat. No. CS-0034814
  • Purity ≥96%
  • MDL No. MFCD09388785
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₃N₃O
  • Molecular Weight 179.22
  • Synonym(s) 5-morpholin-4-ylpyridin-2-ylamine
  • SMILES NC1=CC=C(N2CCOCC2)C=N1

Description

5-Morpholinopyridin-2-amine features a pyridine core functionalized with a morpholine ring at C5 and an amine group at C2, delivering enhanced solubility and hydrogen-bonding capacity. This scaffold integrates readily into kinase inhibitor designs, leveraging its electron-rich heterocycle for target engagement. The molecule exhibits bench-stable handling under standard conditions.

Application

5-Morpholinopyridin-2-amine serves as a versatile building block in medicinal chemistry, enabling efficient construction of kinase inhibitors and other bioactive heterocycles. Its pyridine core provides a robust scaffold for metal-catalyzed cross-coupling reactions, while the morpholine ring enhances solubility and modulates pharmacokinetic properties. The amine functionality facilitates straightforward derivatization via amidation or alkylation, supporting rapid analog generation. This compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for high-throughput synthesis workflows.

Synthesis

  • Route1

    References

    • Toogood, Peter L.; Harvey, Patricia J.; Repine, Joseph T.; Sheehan, Derek J.; VanderWel, Scott N.; Zhou, Hairong; Keller, Paul R.; McNamara, Dennis J.; Sherry, Debra; Zhu, Tong; Brodfuehrer, Joanne; Choi, Chung; Barvian, Mark R.; Fry, David W. Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2388 - 2406
  • Route2
    • null|null
      110-91-8
    • In-stock
      2-Amino-5-chloropyridine|CS-W018533
      1072-98-6
    • ~79%
    • In-stock
      5-Morpholinopyridin-2-amine|CS-0034814
      571189-78-1

    References

    • Anderson, Kevin W.; Tundel, Rachel E.; Ikawa, Takashi; Altman, Ryan A.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2006 , vol. 45, # 39 p. 6523 - 6527
  • Route3

    References

    • Toogood, Peter L.; Harvey, Patricia J.; Repine, Joseph T.; Sheehan, Derek J.; VanderWel, Scott N.; Zhou, Hairong; Keller, Paul R.; McNamara, Dennis J.; Sherry, Debra; Zhu, Tong; Brodfuehrer, Joanne; Choi, Chung; Barvian, Mark R.; Fry, David W. Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2388 - 2406

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   51.38
  • LogP   0.5004
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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