1094070-77-5

Basic information

• Product Name: tert-butyl 2-bromothiazol-5-ylcarbamate
• Synonyms: tert-butyl 2-bromothiazol-5-ylcarbamate;(2-Bromo-thiazol-5-yl)-carbamicacidtert-butylester;Carbamic acid, N-(2-bromo-5-thiazolyl)-, 1,1-dimethylethyl ester;N-(2-Bromo-5-thiazolyl)carbamic acid tert-butyl ester;5-(Boc-aMino)-2-broMothiazole;tert-Butyl N-(2-broMo-5-thiazolyl)carbaMate;tert-butyl N-(2-bromo-1,3-thiazol-5-yl)carbamate;tert-Butyl (2-bromothiazol-5-yl)
• CAS NO: 1094070-77-5
• Molecular Formula: C₈H₁₁BrN₂O₂S
• Molecular Weight: 279.15414
• EINECS: 1592732-453-0
• Mol File: 1094070-77-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 294℃
• Flash Point: 131℃
• Appearance: White to off-white powder
• Density: 1.574
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.83±0.70(Predicted)
• CAS DataBase Reference: tert-butyl 2-bromothiazol-5-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-bromothiazol-5-ylcarbamate(1094070-77-5)
• EPA Substance Registry System: tert-butyl 2-bromothiazol-5-ylcarbamate(1094070-77-5)

Safety Data

• Hazardous Substances Data: 1094070-77-5(Hazardous Substances Data)

Usage

Uses

tert-Butyl (2-bromothiazol-5-yl)carbamate is a useful reactant for the synthesis of imidazo[1,2-a]pyrazine deratives, which could act as Aurora kinase inhibitors.

Upstream product

• 54045-76-0 2-bromo-thiazole-5-carboxylic acid 
• 75-65-0 tert-butyl alcohol 
• 3034-53-5 2-bromo-1,3-thiazole 
• 73210-14-7 N-chloro-N-sodio-tert-butylcarbamate 
• 4248-19-5 tert-butyl carbazate 
• 769069-45-6 tert-butyl N-chlorocarbamate 

Downstream Products

• 1105710-21-1 1,1-dimethylethyl (2-bromo-1,3-thiazol-5-yl)((2S)-2-((((1,1-dimethylethyl)oxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propyl)-carbamate 

Relevant articles and documents

SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS

Disclosed are compounds of Formula (I) N-oxides, or salts thereof, wherein X, Y, A, G, R1, and R5 are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies

Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.

Azole-based inhibitors of AKT/PKB for the treatment of cancer

Through a combination of screening and structure-based rational design, we have discovered a series of N1-(5-(heterocyclyl)-thiazol-2-yl)-3-(4-trifluoromethylphenyl)-1,2-propanediamines that were developed into potent ATP competitive inhibitors of AKT. Studies of linker strand-binding adenine isosteres identified SAR trends in potency and selectivity that were consistent with binding interactions observed in structures of the inhibitors bound to AKT1 and to the counter-screening target PKA. One compound was shown to have acceptable pharmacokinetic properties and to be a potent inhibitor of AKT signaling and of in vivo xenograft tumor growth in a preclinical model of glioblastoma.