335031-01-1

Basic information

• Product Name: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine
• Synonyms: (2-AMINO-5-BROMO-3-PYRIDINYL)METHANOL;(2-AMINO-5-BROMO-PYRIDIN-3-YL)-METHANOL;2-Amino-5-bromopyridine-3-methanol;2-Amino-5-bromo-3-(hydroxymethyl)pyridine;2-Amino-5-Bromo-3-(Hydroxymeth;2-Amino-5-bromo-3-pyridinemethanol;2-broMo-4-ethoxypyriMidine;2-AMino-3-hydroxyMethyl-5-broMopyridine
• CAS NO: 335031-01-1
• Molecular Formula: C₆H₇BrN₂O
• Molecular Weight: 203.04
• Product Categories: pharmacetical;Pyridine series;Hydroxymethyl's;Pyridines;Pyridine;Heterocyclic Compounds;Aromatics;Heterocycles;Heterocycle-Pyridine series
• Mol File: 335031-01-1.mol

Chemical Properties

• Melting Point: 137-140°C
• Boiling Point: 343.5 °C at 760mmHg
• Flash Point: 161.6 °C
• Appearance: Off-white to yellow/Solid
• Density: 1.766 g/cm³
• Vapor Pressure: 2.67E-05mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Acetone, Ethyl Acetate, Methanol
• PKA: 13.16±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(335031-01-1)
• EPA Substance Registry System: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(335031-01-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 335031-01-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Amino-5-bromo-3-(hydroxymethyl)pyridine is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, making it a valuable building block in the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-5-bromo-3-(hydroxymethyl)pyridine is utilized as a pharmaceutical intermediate. Its presence in the molecular structure of various drugs aids in the development of new therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Laboratory Research and Development:
2-Amino-5-bromo-3-(hydroxymethyl)pyridine is also employed in laboratory research and development processes. Its unique properties make it an essential compound for studying various chemical reactions and exploring new methodologies in organic chemistry and drug discovery.
Used in Chemical Production Process:
Furthermore, 2-Amino-5-bromo-3-(hydroxymethyl)pyridine is used in the chemical production process, where it serves as a key intermediate in the manufacturing of various specialty chemicals and materials with specific applications in different industries.

Synthesis

2-Amino-5-bromo-3-(hydroxymethyl)pyridineBromine (8.4 mL, 189.4 mmol) was added dropwise over 1 hour to a solution of 2- amino-3-(hydroxymethyl)pyridine (19.6 g, 157.8 mmol) in acetic acid (350 mL) at room temperature. The reaction mixture was then stirred overnight. After concentration to dryness, the residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 ml_). The aqueous layer was separated and extracted with ethyl acetate (2 x 200 ml_). The combined organic phases were washed with a saturated solution of sodium chloride (200 ml_), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in pentane, the title product was obtained as a yellow solid (27.0 g, 84%).

InChI:InChI=1/C6H7BrN2O/c7-5-1-4(3-10)6(8)9-2-5/h1-2,10H,3H2,(H2,8,9)

Upstream product

• 52833-94-0 2-amino-5-bromonicotinicacid 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 23612-57-9 (2-amino-3-pyridinyl)methanol 

Downstream Products

• 206997-15-1 2-amino-5-bromo-3-pyridinecarbaldehyde 
• 1382485-00-8 4-{4-[6-amino-5-(hydroxymethyl)pyridin-3-yl]phenyl}-N-[5-(2-methyl-1,3-thiazol-4-yl)pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide 
• 1382485-06-4 4-{4-[6-amino-5-(hydroxymethyl)pyridin-3-yl]phenyl}-N-(5-cyanopyridin-2-yl)tetrahydro-2H-pyran-4-carboxamide 
• 1360548-96-4 [2-amino-5-(4-{3-methyl-2-[5-(pyridin-3-yl)-1,2,4-oxadiazol-3-yl]butan-2-yl}phenyl)pyridin-3-yl]methanol 
• 1310530-30-3 {2-amino-5-[1-tert-butyl-2-(5-methoxy-2-pyrazol-1-ylphenyl)-1H-benzimidazol-5-yl]pyridin-3-yl}methanol 
• 1309205-48-8 6-[(1E)-3-oxo-3-(3-phenoxypyrrolidin-1-yl)prop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309205-47-7 6-[(1E)-3-{[3-(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309205-45-5 6-[(1E)-3-oxo-3-(2-phenylpyrrolidin-1-yl)prop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309205-42-2 (E)-6-(3-oxo-3-(3-phenoxyazetidin-1-yl)prop-1-en-1-yl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309205-40-0 6-[(1E)-3-{[4-(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309206-51-6 1'-methyl-6-((E)-3-oxo-3-(3-((E)-1-(benzyloxyimino)ethyl)azetidin-1-yl)prop-1-enyl)-1H-spiro[[1,8]naphthyridine-3,4'-piperidin]-2(4H)-one 
• 1309208-28-3 (E)-4-(4-methoxybenzyl)-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one 
• 1309208-23-8 methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate 
• 1309351-04-9 3-(hydroxymethyl)-6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 

Relevant articles and documents

Novel method for synthesizing 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone

The invention discloses a novel method for synthesizing 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone and relates to the field of chemical synthesis. The method comprises the following steps:by using a four-step synthesis method, performing hydrogen substitution on a benzene ring on 2-amino-3-hydroxymethylpyridine by using bromine so as to generate 2-amino-3-hydroxymethyl-5-bromopyridine;substituting hydroxyl in the 2-amino-3-hydroxymethyl-5-bromopyridine by using chlorine in thionyl chloride so as to generate 2-amino-3-methyl chloride-5-bromopyridine hydrochloride; carrying out an annulation reaction of the 2-amino-3-methyl chloride-5-bromopyridine hydrochloride by using diethyl malonate so as to generate 6-bromine-3-nonanoic acid-ethyl ester-1,2,3,5-tetrahydro-1,8-naphthyridine-2-ketone; finally, under an alkali condition, removing carboxylic acid carbethoxy from the 6-bromine-3-nonanoic acid-ethyl ester-1,2,3,5-tetrahydro-1,8-naphthyridine-2-ketone, thereby obtaining a final product, namely 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone. The method is low in raw material cost, simple in synthesis process, not harsh in reaction condition, safe and convenient to operate, high in final product yield, and applicable to large-scale industrial production.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

NOVEL HETEROCYCLIC ACRYLAMIDES AND THEIR USE AS PHARMACEUTICALS

The invention relates to novel heterocyclic acrylamide compounds (I), to the preparation of the compounds and intermediates used therein, to the use of the compounds as antibacterial medicaments and pharmaceutical compositions containing the compounds.

FAB I INHIBITORS

Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

Methods of agonizing and antagonizing FabK

The invention provides methods for using agonists and antagonists of FabK polypeptides, particularly to modulate the metabolism of bacteria or to treat bacterial infection.

Indole naphthyridinones as inhibitors of bacterial enoyl-ACP reductases FabI and FabK

Bacterial enoyl-ACP reductase (FabI) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis and is an attractive target for the development of novel antibacterial agents. Previously we reported the development of FabI inhibitor 4 with narrow spectrum antimicrobial activity and in vivo efficacy against Staphylococcus aureus via intraperitoneal (ip) administration. Through iterative medicinal chemistry aided by X-ray crystal structure analysis, a new series of inhibitors has been developed with greatly increased potency against FabI-containing organisms. Several of these new inhibitors have potent antibacterial activity against multidrug resistant strains of S. aureus, and compound 30 demonstrates exceptional oral (po) in vivo efficacy in a S. aureus infection model in rats. While optimizing FabI inhibitory activity, compounds 29 and 30 were identified as having low micromolar FabK inhibitory activity, thereby increasing the antimicrobial spectrum of these compounds to include the FabK-containing pathogens Streptococcus pneumoniae and Enterococcus faecalis. The results described herein support the hypothesis that bacterial enoyl-ACP reductases are valid targets for antibacterial agents.