302963-94-6

Basic information

• Product Name: N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID
• Synonyms: N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID;2-TERT-BUTOXYCARBONYLAMINO-4-METHYL-THIAZOLE-5-CARBOXYLIC ACID;5-Thiazolecarboxylicacid,2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-(9CI);N-Boc-2-amino-4-methylthiazole-5-carboxylic acid;5-Thiazolecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-
• CAS NO: 302963-94-6
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29
• Product Categories: N-BOC
• Mol File: 302963-94-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.359g/cm³
• Refractive Index: 1.592
• Storage Temp.: 2-8°C
• PKA: 1.39±0.37(Predicted)
• CAS DataBase Reference: N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID(302963-94-6)
• EPA Substance Registry System: N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID(302963-94-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 302963-94-6(Hazardous Substances Data)

Usage

General Description

N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID is a chemical compound that belongs to the class of thiazole carboxylic acids. It is a derivative of 4-methylthiazole and contains an N-tert-butoxycarbonyl (N-BOC) protecting group on the amino group. N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID has potential applications in organic synthesis and pharmaceutical research due to its unique structure and properties. It can be used as a building block for the synthesis of various bioactive molecules, drugs, and agrochemicals. Overall, N-BOC-AMINO-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID is a valuable chemical compound with versatile and promising applications in the field of chemistry and drug discovery.

InChI:InChI=1/C10H14N2O4S/c1-5-6(7(13)14)17-8(11-5)12-9(15)16-10(2,3)4/h1-4H3,(H,13,14)(H,11,12,15)

Upstream product

• 244236-52-0 ethyl 2-[[(tert-butyloxy)carbonyl]amino]-4-methyl-1,3-thiazole-5-carboxylate 
• 7210-76-6 ethyl-2-amino-4-methylthiazole-5-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1246830-32-9 (S)-3-(4'-cyano-biphenyl-4-yl)-2-({(S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-propionic acid methyl ester 
• 302957-95-5 [5-[[(2,4-dichlorophenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid, 1.1-dimethylethyl ester 
• 302958-02-7 [5-[[(4-bromo-2,6-dimethylphenyl)amino]-carbonyl]-4-methyl-2-thiazolyl]carbamic acid 1,1-dimethylethyl ester 
• 302958-03-8 [4-methyl-5-[[[2-methyl-6-(1-methylethyl)phenyl]-amino]carbonyl]-2-thiazolyl]carbamic acid 1,1-dimethylethyl ester 
• 302958-40-3 [5-[[(2,6-dimethylphenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid 1,1-dimethylethyl ester 
• 302958-05-0 [4-methyl-5-[[(2-methylphenyl)amino]carbonyl]-2-thiazolyl]carbamic acid 1,1-dimethylethyl ester 
• 302957-93-3 [5-[[phenylamino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid, 1,1-dimethylethyl ester 
• 302957-83-1 [5-[[(2,4,6-Trimethylphenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid, 1,1-dimethylethyl ester 
• 302958-04-9 [5-[[(2,4-dimethylphenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid 1,1-dimethylethyl ester 

Relevant articles and documents

Synthesis of GluN2A-selective NMDA receptor antagonists with an electron-rich aromatic B-ring

Glutamatergic N-Methyl-D-aspartate (NMDA) receptors are heterotetrameric ion channels that can be comprised of different subunits. GluN2A subunit-containing NMDA receptors are associated with diseases like anxiety, depression, and schizophrenia. However,

2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6- [4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-1, 3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor

2-Aminothiazole (1) was discovered as a novel Src family kinase inhibitor template through screening of our internal compound collection. Optimization through successive structure-activity relationship iterations identified analogs 2 (Dasatinib, BMS-354825) and 12m as pan-Src inhibitors with nanomolar to subnanomolar potencies in biochemical and cellular assays. Molecular modeling was used to construct a putative binding model for Lck inhibition by this class of compounds. The framework of key hydrogen-bond interactions proposed by this model was in agreement with the subsequent, published crystal structure of 2 bound to structurally similar Abl kinase. The oral efficacy of this class of inhibitors was demonstrated with 12m in inhibiting the proinflammatory cytokine IL-2 ex vivo in mice (ED50 ～ 5 mg/kg) and in reducing TNF levels in an acute murine model of inflammation (90% inhibition in LPS-induced TNFα production when dosed orally at 60 mg/kg, 2 h prior to LPS administration). The oral efficacy of 12m was further demonstrated in a chronic model of adjuvant arthritis in rats with established disease when administered orally at 0.3 and 3 mg/kg twice daily. Dasatinib (2) is currently in clinical trials for the treatment of chronic myelogenous leukemia.

Discovery and initial SAR of 2-amino-5-carboxamidothiazoles as inhibitors of the Src-family kinase p56Lck

A novel series of 2-amino-5-carboxamidothiazoles were identified as inhibitors of Lck. Structure-activity studies demonstrate the structural requirements for potent Lck activity. Cyclopropylamide 11d is a potent Lck inhibitor having sub-micromolar activity in a PBL proliferation assay.