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CS-W001157 4
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3-Amino-6-chloropyridine-2-carboxamide

  • CAS No. 175358-01-7

  • Cat. No. CS-0053878
  • Purity≥96%
  • MDL No.None

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

3-Amino-6-chloropyridine-2-carboxamide|CS-0053878

Structure of 175358-01-7

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General Information

  • CAS No. 175358-01-7
  • Cat. No. CS-0053878
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆ClN₃O
  • Molecular Weight 171.58
  • Synonym(s) 6-Chloro-3-aminopyridine-2-carboxamide
  • SMILES O=C(N)C1=NC(Cl)=CC=C1N

Description

3-Amino-6-chloropyridine-2-carboxamide features a pyridine core bearing amino, chloro, and carboxamide functionalities, enabling versatile integration into bioactive scaffolds. The electron-deficient ring facilitates nucleophilic substitution, while the amide group enhances solubility and hydrogen bonding capacity. This compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and antimicrobial agents.

Application

3-Amino-6-chloropyridine-2-carboxamide serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through nucleophilic substitution and coupling reactions. Its ortho-amino and carboxamide functionalities offer complementary reactivity for derivatization, while the chloro group facilitates transition-metal-catalyzed transformations. The compound exhibits bench stability and is compatible with standard purification protocols, making it well-suited for iterative synthesis campaigns in API development.

Synthesis

  • Route1

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH Patent: US2012/94976 A1, 2012 ; Location in patent: Page/Page column 48-49 ;
  • Route2

    References

    • ELI LILLY AND COMPANY Patent: WO2005/97805 A1, 2005 ; Location in patent: Page/Page column 49 ;
  • Route3

    References

    • US2012/238587 A1, ; US 20120238587 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   82
  • LogP   0.4161
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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