tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate

Name: tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 633283-63-3
Cat. No. CS-0202151
Purity≥98%
MDL No.None

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tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate|CS-0202151

Structure of 633283-63-3

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General Information

CAS No. 633283-63-3
Cat. No. CS-0202151
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀ClN₃O₂
Molecular Weight 297.78
Synonym(s) 4-(2-Chloro-4-pyridinyl)-1-Piperazinecarboxylic acid 1,1-dimethylethyl ester
SMILES O=C(N1CCN(C2=CC(Cl)=NC=C2)CC1)OC(C)(C)C

Description

tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate features a chloropyridine moiety coupled to a piperazine scaffold, enabling direct incorporation into kinase inhibitors and bioactive heterocycles. The tert-butyl ester group provides stability and facilitates deprotection under mild acidic conditions. This compound serves as a key intermediate in the synthesis of pharmaceutical candidates targeting receptor tyrosine kinases.

Application

tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to pyridyl-piperazine scaffolds commonly found in kinase inhibitors and CNS-targeted therapeutics. The tert-butyl carbamate group offers excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. The 2-chloropyridine moiety provides a reactive handle for palladium-catalyzed cross-coupling reactions, including Suzuki and Buchwald-Hartwig amination, supporting diverse structural elaboration in lead optimization campaigns.

Synthesis

Route1
- In-stock
  
  73583-37-6
- 57260-71-6
- ~98%
- In-stock
  
  633283-63-3
References
- JANSSEN PHARMACEUTICA NV Patent: WO2009/152325 A1, 2009 ; Location in patent: Page/Page column 47-48 ; WO 2009/152325 A1
Route2
- In-stock
  
  26452-80-2
- 57260-71-6
- ~51%
- 936368-68-2
- In-stock
  
  633283-63-3
References
- Gobbi, Luca; Jaeschke, Georg; Rodriguez Sarmiento, Rosa Maria; Steward, Lucinda Patent: US2010/75979 A1, 2010 ; Location in patent: Page/Page column 9; 11 ; US 20100075979 A1
Route3
- In-stock
  
  153034-86-7
- 57260-71-6
- ~%
- In-stock
  
  633283-63-3
References
- ALMAC DISCOVERY LIMITED; HARRISON, Timothy; BURKAMP, Frank; JORDAN, Linda; BELL, Mark; JANSSEN, Dominic; MIEL, Hugues; MCFARLAND, Mary Patent: WO2012/69852 A1, 2012 ; Location in patent: Page/Page column 36 ;

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 45.67
LogP 2.7921
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Key Words

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tert-Butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate

CAS No. 633283-63-3

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