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

Name: Benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate
Brand: ChemScene
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CAS No. 1420478-88-1
Cat. No. CS-0049898
Purity≥97%
MDL No.MFCD30184899

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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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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.

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

Computational Chemistry Data

TPSA 85.75
LogP 3.5477
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 3

Safety Information

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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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Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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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

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