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Benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate

  • CAS No. 1420478-88-1

  • Cat. No. CS-0049898
  • Purity≥97%
  • MDL No.MFCD30184899

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

Benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate|CS-0049898

Structure of 1420478-88-1

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General Information

  • CAS No. 1420478-88-1
  • Cat. No. CS-0049898
  • Purity ≥97%
  • MDL No. MFCD30184899
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₈BrN₅O₂
  • Molecular Weight 416.27
  • Synonym(s) 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-
  • SMILES NC1=NC=CN2C(=NC(Br)=C12)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1

Description

Benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate is a chiral imidazopyrazine derivative featuring a brominated heterocyclic core and a protected pyrrolidine moiety. This scaffold integrates a reactive bromine atom with an amine-functionalized ring system, enabling downstream coupling reactions in medicinal chemistry. The benzyl ester group provides stability and facilitates selective deprotection under standard conditions. The stereochemistry at the pyrrolidine center ensures defined spatial orientation critical for target engagement in drug discovery applications.

Application

Benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate serves as a versatile building block for the synthesis of imidazopyrazine-containing pharmaceuticals. The molecule combines a bromo-imidazopyrazine core with a chiral pyrrolidine moiety, enabling efficient late-stage functionalization via Pd-catalyzed cross-coupling reactions. Its benzyl carbamate group provides excellent stability and ease of purification, while the 8-amino functionality allows for further derivatization. This compound is particularly valuable in medicinal chemistry campaigns targeting kinase inhibitors and antiviral agents.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   85.75
  • LogP   3.5477
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   3

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