169335-50-6

Basic information

• Product Name: tert-butyl 5-chloropyrazine-2-carboxylate
• Synonyms: 2-pyrazinecarboxylic acid, 5-chloro-, 1,1-dimethylethyl ester
• CAS NO: 169335-50-6
• Molecular Formula: C₉H₁₁ClN₂O₂
• Molecular Weight: 214.6488
• Mol File: 169335-50-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 277.8°C at 760 mmHg
• Flash Point: 121.8°C
• Density: 1.224g/cm³
• Vapor Pressure: 0.00444mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: tert-butyl 5-chloropyrazine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 5-chloropyrazine-2-carboxylate(169335-50-6)
• EPA Substance Registry System: tert-butyl 5-chloropyrazine-2-carboxylate(169335-50-6)

Safety Data

• Hazardous Substances Data: 169335-50-6(Hazardous Substances Data)

Upstream product

• 36070-80-1 5-chloropyrazinoic acid 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 88625-23-4 5-chloropyrazine-2-carbonyl chloride 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 1174323-36-4 5-(2,2,2-trifluoroethoxy)-pyrazine-2-carboxylic acid 
• 710321-51-0 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid hydroxyamide 
• 710322-37-5 5-[2(R)-(3-chloro-4-methanesulfonylphenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid tert-butoxy-amide 
• 710322-36-4 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid 
• 710322-35-3 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid tertbutyl ester 
• 1310809-49-4 C₁₇H₁₇BrN₂O₅ 
• 1310808-01-5 5-[3-bromo-5-(methoxycarbonyl)phenoxy]pyrazine-2-carboxylic acid 
• 710322-34-2 5-amino-pyrazine-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 4. Discovery of Potent 6-(2-(Alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles

A series of 6-hetaryloxy benzoxaborole compounds was designed and synthesized for a structure-activity relationship (SAR) investigation to assess the changes in antimalarial activity which result from 6-aryloxy structural variation, substituent modification on the pyrazine ring, and optimization of the side chain ester group. This SAR study discovered highly potent 6-(2-(alkoxycarbonyl)pyrazinyl-5-oxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 27-34) with IC50s = 0.2-22 nM against cultured Plasmodium falciparum W2 and 3D7 strains. Compound 9 also demonstrated excellent in vivo efficacy against P. berghei in infected mice (ED90 = 7.0 mg/kg).

Identification of RO4597014, a glucokinase activator studied in the clinic for the treatment of type 2 diabetes

To resolve the metabolite redox cycling associated with our earlier clinical compound 2, we carried out lead optimization of lead molecule 1. Compound 4 showed improved lipophilic ligand efficiency and demonstrated robust glucose lowering in diet-induced obese mice without a liability in predictive preclinical drug safety studies. Thus, it was selected as a clinical candidate and further studied in type 2 diabetic patients. Clinical data suggests no evidence of metabolite cycling, which is consistent with the preclinical profiling of metabolism.

Pyrazinoic Acid Esters with Broad Spectrum in Vitro Antimycobacterial Activity

A series of substituted pyrazinoic acid esters has been prepared and examined for their in vitro activity against Mycobacterium avium and Mycobacterium kansasii as well as mycobacterium tuberculosis.Modification of both the pyrazine nucleus and the ester functionality have been very successfull in expanding the activity of pyrazinamide to include M. avium and M. kansasii, organisms normally not susceptible to pyrazinamide.Several of these compounds have activities 100-1000-fold greater than that of pyrazinamide against M. tuberculosis.