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

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

Uses

Used in Pharmaceutical Research and Drug Development:
5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is used as a key intermediate for the synthesis of various pharmaceutical compounds due to its unique structural features and the biological activity of its constituent groups.
Used in Agrochemical Manufacturing:
5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is also utilized in the production of agrochemicals, where its reactivity and structural properties contribute to the development of effective products for agricultural applications.
Used in Dye Production:
5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE is employed as a chemical intermediate in the manufacturing of dyes, leveraging its chemical properties to create a range of colorants for various industries.
Used in the Synthesis of Fine Chemicals:
5-BROMO-2-(1-METHYL-1H-TETRAZOL-5-YL)-PYRIDINE serves as an important intermediate in the synthesis of fine chemicals, where its specific reactivity and functional groups are harnessed to produce high-quality specialty chemicals for diverse applications.

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 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 380380-60-9 5-bromo-2-(2H-tetrazol-5-yl)pyridine 

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 
• 883231-14-9 (6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)boronic acid 
• 1056039-83-8 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 

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.

A oxazolidinone compounds of preparation method (by machine translation)

The invention provides a oxazolidinone compounds of the preparation method. Specifically provides the type 1 compound preparation method. The formula 1 compound preparation method comprises, formula 2 N - methyl - D - grape amine compound in the presence of a catalytic reduction, direct formula 1 compound. The present invention provides a preparation has simplified the reaction step, shorten the reaction route, can make the final yield of the product is higher, and, better purity. (by machine translation)

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.

ANTIMICROBIAL HETEROCYCLIC COMPOUNDS FOR TREATMENT OF BACTERIAL INFECTIONS

The present invention provides heterocyclic compounds of the following formula (I) : or pharmaceutically acceptable salts, prodrugs, solvates, or hydrates thereof useful as antibacterial agents, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.

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.

NOVEL OXAZOLIDINONE DERIVATIVES

The present invention relates to novel derivatives of oxazolidinone, a method thereof and pharmaceutical compositions comprising the derivatives for use in an antibiotic. The oxazolidinone derivatives of the present invention show inhibitory activity against a broad spectrum of bacteria and lower toxicity. The prodrugs, prepared by reacting the compound having hydroxyl group with amino acid or phosphate, have an excellent efficiency on solubility thereof against water. Further, the derivatives of the present invention may exert potent antibacterial activity versus various human and animal pathogens, including Gram-positive bacteria such as Staphylococi, Enterococci and Streptococi, anaerobic microorganisms such as Bacteroides and Clostridia, and acid-resistant microorganisms such as Mycobacterium tuberculosis and Mycobacterium avium. Accordingly, the compositions comprising the oxazolidinone are used in an antibiotic.

3- `4- {6-SUBSTITUTED ALKANOYL) PYRIDIN-3-YL} -3-PHENYL! -5- (1H-1, 2, 3-TRIAZOL-1-YLMETHYL) -1, 3-OXAZOLIDIN-2-ONES AS ANTIBACTERIAL AGENTS

Compounds of formula (I) as well as pharmaceutically-acceptable salts and pro-drugs thereof are disclosed wherein R1, R2, R3, and R4 are defined herein. Also disclosed are processes for making compounds of formula (I) as well as methods of using compounds of formula (I) for treating bacterial infections.

3- {4- (PYRIDIN-3-YL) PHENYL} -5- (1H-1, 2, 3-TRIAZOL-1-YLMETHYL) -1, 3-OXAZOLIDIN-2-ONES AS ANTIBACTERIAL AGENTS

Compounds of formula (I), as well as pharmaceutically-acceptable salts and pro-drugs thereof, are disclosed wherein R1, R2, R3, and R4 are defined herein. Also disclosed are processes for making compounds of formula (I) as well as methods of using compounds of formula (I) for treating bacterial infections.

Antibacterial compounds with improved pharmacokinetic profiles

Antibacterial compounds with improved pharmacokinetic profiles having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates used in the processes, compositions containing the compounds, and methods for prophylaxis and treatment of bacterial infections using the compounds are disclosed.

CHEMICAL COMPOUNDS

A compound of the formula (I), or a pharmaceutically-acceptable salt, or in-vivo hydrolysable ester thereof: Wherein C is selected from (D) and (E), R2a, R6a, and R3a ar e independently selected from for example H, CF3, Me and Et; R2b and R6b are independently selected from for example H,F, CF3, Me and Et; R1b is for example optionally substituted diazolyl, triazolyl or tetrazolyl; R4 is for example an optionally substituted 5- or 6-membered heterocyclic ring system. Methods for making compounds of the formula (I), compositions containing them and their use as antibacterial agents are also described.