tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Name: tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 1151665-15-4
Cat. No. CS-W022989
Purity≥97%
MDL No.MFCD10565958

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate|CS-W022989

Structure of 1151665-15-4

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General Information

CAS No. 1151665-15-4
Cat. No. CS-W022989
Purity ≥97%
MDL No. MFCD10565958
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇ClN₂O₂
Molecular Weight 268.74
Synonym(s) TERT-BUTYL 2-CHLORO-7,8-DIHYDRO-1,6-NAPHTHYRIDINE-6(6H)-CARBOXYLATE
SMILES O=C(N1CC2=C(N=C(Cl)C=C2)CC1)OC(C)(C)C

Description

tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate features a chlorinated dihydronaphthyridine core with a tert-butyl ester handle, enabling direct incorporation into heterocyclic scaffolds. This bench-stable intermediate supports efficient derivatization in medicinal chemistry campaigns targeting kinase inhibitors and DNA-interactive agents.

Application

tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate serves as a versatile building block for the synthesis of naphthyridine-based scaffolds. The chloride functionality enables palladium-catalyzed cross-coupling reactions, while the protected pyridone moiety offers stability and compatibility with diverse reaction conditions. Its bench-stable nature and ease of purification facilitate efficient integration into medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  766545-20-4
- In-stock
  
  24424-99-5
- ~99%
- In-stock
  
  1151665-15-4
References
- Li, Zhihong; Wang, Xianghong; Eksterowicz, John; Gribble, Michael W.; Alba, Grace Q.; Ayres, Merrill; Carlson, Timothy J.; Chen, Ada; Chen, Xiaoqi; Cho, Robert; Connors, Richard V.; Degraffenreid, Michael; Deignan, Jeffrey T.; Duquette, Jason; Fan, Pingchen; Fisher, Benjamin; Fu, Jiasheng; Huard, Justin N.; Kaizerman, Jacob; Keegan, Kathleen S.; Li, Cong; Li, Kexue; Li, Yunxiao; Liang, Lingming; Liu, Wen; Lively, Sarah E.; Lo, Mei-Chu; Ma, Ji; McMinn, Dustin L.; Mihalic, Jeffrey T.; Modi, Kriti; Ngo, Rachel; Pattabiraman, Kanaka; Piper, Derek E.; Queva, Christophe; Ragains, Mark L.; Suchomel, Julia; Thibault, Steve; Walker, Nigel; Wang, Xiaodong; Wang, Zhulun; Wanska, Malgorzata; Wehn, Paul M.; Weidner, Margaret F.; Zhang, Alex J.; Zhao, Xiaoning; Kamb, Alexander; Wickramasinghe, Dineli; Dai, Kang; McGee, Lawrence R.; Medina, Julio C. Journal of Medicinal Chemistry, 2014 , vol. 57, # 8 p. 3430 - 3449
Route2
- In-stock
  
  210539-04-1
- In-stock
  
  24424-99-5
- ~73%
- In-stock
  
  1151665-15-4
References
- Takeda Pharmaceutical Company Limited Patent: EP2216023 A1, 2010 ; Location in patent: Page/Page column 103 ; EP 2216023 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

Quality Control

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Computational Chemistry Data

TPSA 42.43
LogP 3.0282
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

CAS No. 1151665-15-4

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