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2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

  • CAS No. 1035219-96-5

  • Cat. No. CS-W006953
  • Purity≥95%
  • MDL No.MFCD14706758

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

2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one|CS-W006953

Structure of 1035219-96-5

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General Information

  • CAS No. 1035219-96-5
  • Cat. No. CS-W006953
  • Purity ≥95%
  • MDL No. MFCD14706758
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂OS
  • Molecular Weight 233.09
  • Synonym(s) 2-Bromo-6,7-dihydrothiazolo-[5,4-c]pyridin-4(5H)-one
  • SMILES O=C1C(SC(Br)=N2)=C2CCN1

Description

2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one features a fused thiazolopyridinone core with a bromine substituent at the 2-position, enabling direct functionalization in late-stage diversification. The saturated five-membered ring enhances solubility and stability under standard conditions, while the carbonyl group supports hydrogen bonding in target engagement. This scaffold serves as a privileged motif in medicinal chemistry for kinase inhibition and protein-protein interaction modulation.

Application

2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one serves as a versatile heterocyclic building block for medicinal chemistry and synthetic methodology development. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the thiazolopyridinone core provides a rigid, electron-deficient scaffold suitable for targeted functionalization. The compound exhibits good bench stability and facilitates efficient derivatization under standard reaction conditions.

Synthesis

  • Route1
    • In-stock
      2-Amino-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one hydrochloride|CS-0115628
      1312412-89-7
    • ~54%
    • In-stock
      2-Bromo-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one|CS-W006953
      1035219-96-5

    References

    • Bartolome-Nebreda, Jose Manuel; Conde-Ceide, Susana; Delgado, Francisca; Iturrino, Laura; Pastor, Joaquin; Pena, Miguel Angel; Trabanco, Andres A.; Tresadern, Gary; Wassvik, Carola M.; Stauffer, Shaun R.; Jadhav, Satyawan; Gogi, Kiran; Vinson, Paige N.; Noetzel, Meredith J.; Days, Emily; Weaver, C. David; Lindsley, Craig W.; Niswender, Colleen M.; Jones, Carrie K.; Conn, P. Jeffrey; Rombouts, Frederik; Lavreysen, Hilde; Macdonald, Gregor J.; Mackie, Claire; Steckler, Thomas Journal of Medicinal Chemistry, 2013 , vol. 56, # 18 p. 7243 - 7259
  • Route2

    References

    • JANSSEN PHARMACEUTICA NV; MACDONALD, Gregor, James; TRABANCO-SUAREZ, Andres, Avelino; CONDE-CEIDE, Susana; TRESADERN, Gary, John; BARTOLOME-NEBREDA, Jose, Manuel; PASTOR-FERNANDEZ, Joaquin Patent: WO2011/73339 A1, 2011 ; Location in patent: Page/Page column 43 ; WO 2011/073339 A1
  • Route3

    References

    • WO2011/73339 A1, ; WO 2011/073339 A1

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   41.99
  • LogP   1.1915
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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