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Methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate

  • CAS No. 91476-81-2

  • Cat. No. CS-W022856
  • Purity≥95%
  • MDL No.MFCD09909673

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

Methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate|CS-W022856

Structure of 91476-81-2

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General Information

  • CAS No. 91476-81-2
  • Cat. No. CS-W022856
  • Purity ≥95%
  • MDL No. MFCD09909673
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁N₃O₂
  • Molecular Weight 181.19
  • Synonym(s) Imidazo[1,2-a]pyrazine-2-carboxylic acid, 5,6,7,8-tetrahydro-, methyl ester (9CI)
  • SMILES O=C(C1=CN2C(CNCC2)=N1)OC

Description

Methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate is a heterocyclic ester featuring a saturated imidazopyrazine core. This bench-stable compound integrates a methyl ester group at the C2 position, enabling direct incorporation into synthetic sequences without pre-activation. The fused ring system provides rigidity and enhanced metabolic stability, making it valuable for medicinal chemistry applications requiring structural diversity and improved pharmacokinetic profiles.

Application

Methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and process development. The tetrahydroimidazopyrazine core exhibits favorable stability and functional group tolerance, enabling straightforward derivatization via standard coupling and reduction protocols. Its methyl ester functionality facilitates selective transformations and purification by chromatography, making it well-suited for iterative synthesis of bioactive scaffolds in drug discovery workflows.

Synthesis

  • Route1
    • Methyl imidazo[1,2-a]pyrazine-2-carboxylate|CS-0456651
      87597-22-6
    • ~%
    • In-stock
      Methyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylate|CS-W022856
      91476-81-2

    References

    • Journal of Chemical Research, Miniprint, , # 2 p. 468 - 480

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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   56.15
  • LogP   -0.2271
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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