380380-63-2

Basic information

• Product Name: 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE
• Synonyms: REF DUPL: 5-Bromo-2-(1-methyl-1H-tetrazol-5-yl)-pyridine;Pyridine, 5-broMo-2-(1-Methyl-1H-tetrazol-5-yl)-;2-(1-Methyl-5-tetrazolyl)-5-bromopyridine;Tedizolid Impurity B;Tedizolidted Impurity B
• CAS NO: 380380-63-2
• Molecular Formula: C₇H₆BrN₅
• Molecular Weight: 240.06
• EINECS: 1592732-453-0
• Product Categories: Tedizolid intermediates
• Mol File: 380380-63-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 375.19°C at 760 mmHg
• Flash Point: 180.709°C
• Appearance: /
• Density: 1.853g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.759
• Storage Temp.: 2-8°C
• PKA: 0.52±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE(380380-63-2)
• EPA Substance Registry System: 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE(380380-63-2)

Safety Data

• Hazardous Substances Data: 380380-63-2(Hazardous Substances Data)

Usage

General Description

5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is a chemical compound with a pyridine ring that is substituted with a bromine atom at the 5-position and a 1-methyl-1H-tetrazol-5-yl group at the 2-position. It is commonly used in pharmaceutical research and drug development as a building block for the synthesis of various biologically active compounds. The 1-methyl-1H-tetrazol-5-yl group is a common pharmacophore in many pharmaceuticals and is known for its biological activity. The bromine atom provides a unique reactivity for further chemical derivatization. 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is also used in the manufacturing of agrochemicals, dyes, and other fine chemicals. Overall, 5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is an important intermediate in the synthesis of various pharmaceutical and agrochemical compounds.

InChI:InChI=1/C7H6BrN5/c1-13-7(10-11-12-13)6-3-2-5(8)4-9-6/h2-4H,1H3

Upstream product

• 74-88-4 methyl iodide 
• 380380-60-9 2-(1,2,3,4-tetrazol-5-yl)-5-bromopyridine 
• 624-28-2 2,5-dibromopyridine 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 380380-60-9 5-bromo-2-(2H-tetrazol-5-yl)pyridine 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 717123-26-7 [(⁽⁵⁵⁾-3-{3-FLUORO-4-[6-(1-METHYL-1H-TETRAZOL-5-YL)PYRID-3-YL]PHENYL}-1.3-OXAZOLIDIN-2-ON-5-YL)METHYL]CARBAMIC acid methyl ester 
• 1056039-85-0 2-(1-methyl-1H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1056039-83-8 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 883231-14-9 (6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)boronic acid 

Relevant articles and documents

Copper Catalyzed Assembly of N-Aryloxazolidinones: Synthesis of Linezolid, Tedizolid, and Rivaroxaban

The total synthesis of oxazolidinone-based pharmaceuticals, linezolid, tedizolid and rivaroxaban is reported. They are synthesized using a recently reported copper-catalyzed one-pot cyclization and arylation as the key step to construct the N-aryloxazolidinone core. Active pharmaceutical ingredients (API) were synthesized from a common synthetic pool of a simple protected amino alcohol in 22 %, 61 % and 40 % total synthesis yields, respectively.

Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent

A series of novel substituted pyridyl phenyl oxazolidinone analogues were synthesized and their structure-activity relationship (SAR) was investigated based on in vitro and in vivo antibacterial activities. The minimum inhibitory concentrations (MICs) of the synthesized compounds against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) ranged from 0.12 to 2.0 μg/mL, and against Haemophilus influenzae (Hi) from 2.0 to 8.0 μg/mL. Compared to linezolid, only four compounds (11, 12, 21 and 29) showed higher in vitro antibacterial activities and better in vivo protective effects in mice. To improve the aqueous solubility, various prodrugs of compound 11 (DA-7157), which exerted a potency that was enhanced by 2-8-fold compared to that of linezolid, were synthesized. Among the prodrugs, the phosphate compound 42 exhibited excellent aqueous solubility (>50 mg/mL in DW) and good pharmacokinetic profiles, along with better in vivo efficacy than linezolid. This compound 42 is currently undergoing clinical trials with the brand name Torezolid.

OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS

The present invention relates to certain substituted phenyl oxazolidinones and to processes for the synthesis of the same. This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria, for example, multiple-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms, for example, Bacterioides spp. and Clostridia spp. species, and acid fast organisms, for example, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.