137433-23-9

Basic information

• Product Name: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol
• CAS NO: 137433-23-9
• Molecular Formula: C₁₈H₂₆ClN₃O
• Molecular Weight: 335.8715
• Mol File: 137433-23-9.mol

Chemical Properties

• Boiling Point: 516.7°C at 760 mmHg
• Flash Point: 266.3°C
• Density: 1.176g/cm³
• Vapor Pressure: 1.68E-11mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(137433-23-9)
• EPA Substance Registry System: 2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol(137433-23-9)

Safety Data

• Hazardous Substances Data: 137433-23-9(Hazardous Substances Data)

Usage

General Description

2-[{(4R)-4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol, also known as Tafenoquine, is a medication used for the prevention of malaria. It belongs to the class of 8-Aminoquinoline antimalarial drugs and works by effectively killing the malaria parasites in the liver and preventing the development of the disease. Tafenoquine is thought to interfere with the parasite's ability to break down hemoglobin, leading to the build-up of toxic heme molecules that ultimately kill the parasites. It has a long half-life and can provide protection against malaria for up to several months after a single dose, making it particularly useful for travelers to malaria-endemic areas. However, it comes with potential side effects such as nausea, vomiting, and headache.

Upstream product

• 86-98-6 4,7-dichloroquinoline 
• 747-36-4 Plaquenil 
• 69559-11-1 rac-5--2-pentanamine 
• 74509-79-8 5-(N-ethyl-N-2-hydroxyethylamine)-2-pentanone 
• 3695-29-2 5-iodo-2-pentanone 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 103526-68-7 7-chloro-4-fluoroquinoline 
• 613-18-3 2,3-dichloroquinoline 
• 747-36-4 (±)-hydroxychloroquine sulfate 
• 159346-86-8 R(-)-5--2-pentanamine 
• 118-42-3 hydroxychloroquine 
• 1198-40-9 4-amino-7-chloroquinoline 
• 155204-10-7 S(+)-5--2-pentanamine 

Downstream Products

• 137433-23-9 (R)-Hydroxychloroquine 
• 137433-23-9 (S)-Hydroxychloroquine 
• 158749-75-8 C₁₈H₂₆ClN₃O*(x)H₃O₄P 
• 158749-75-8 C₁₈H₂₆ClN₃O*(x)H₃O₄P 
• 747-36-4 Plaquenil 
• 747-36-4 (S)-hydroxychloroquine sulfate 
• 747-36-4 C₁₈H₂₆ClN₃O*(x)H₂O₄S 
• 747-36-4 R-(-)-hydroxychloroquine sulfate 

Relevant articles and documents

A Practical Synthesis of the Enantiomers of Hydroxychloroquine

An efficient synthesis of the enantiomeric forms of hydroxychloroquine is described.The method is suitable for the production of multigram quantities of the dihydrogenphosphate salts (R)-1b and (S)-1b.

Enantioselective analyses of chloroquine and hydroxychloroquine in rat liver microsomes through chiral liquid chromatography–tandem mass spectrometry

An efficient, sensitive and selective liquid chromatography–tandem mass spectrometry (LC–MS/MS) chiral analysis method was established for determination of chloroquine and hydroxychloroquine enantiomers in rat liver microsomes. Effects of polysaccharide c

Synthesis and evaluation of enantiomers of hydroxychloroquine against SARS-CoV-2 in vitro

Since the end of 2019, the outbreak of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) has evolved into a global pandemic. There is an urgent need for effective and low-toxic antiviral drugs to remedy Remdesivir's limitation. Hydroxychloroqui

An asymmetric synthesis method of optically pure (R)/(S)-hydroxychloroquine side chains

The present invention provides an optically pure (R)/ (S) - hydroxychloroquine synthesis method, using a splitting reagent to (±) -2- [(4-aminopentyl)ethylamine] ethanol is split, and recrystallization purification, purified to give optically pure (R) / (S)-2- [(4-aminopentyl) ethylamine] ethanol, the resulting single configuration of hydroxychloroquine side chain and 4,7-dichloroquinoline reaction directly to obtain a single configuration of hydroxychloroquine sulfate. The method has a simple route, easy to obtain raw materials, high yield, good three-dimensional selectivity (ee% >99%), simple operation and green environmental protection, suitable for large-scale scale production.

Preparation method of hydroxychloroquine

The invention relates to a preparation method of hydroxychloroquine, which comprises the following steps: protecting hydroxyl of 5-(N-ethyl-N-ethoxyl)-2-aminopentane through a silanization reagent, removing amino protons from tetrahydrofuran or toluene by using a bis(trimethylsilyl lithium amide) solution to form amino anions, and carrying out a substitution reaction with 4.7 dichloroquinoline to generate hydroxychloroquine. The hydroxychloroquine and sulfuric acid are salified in an alcoholic solution to generate hydroxychloroquine sulfate, and the hydroxychloroquine sulfate preparation method provided by the invention has the characteristics of low toxicity, low pollution, high purity, low reaction temperature, short reaction time, high yield and the like, and is suitable for industrialization.

Optically active chloroquine and hydroxychloroquine and analogues thereof, and preparation method, composition and application of optically active chloroquine and hydroxychloroquine

The invention provides a rapid and simple method for preparing optically active chloroquine, hydroxychloroquine and analogues thereof, which comprises the following steps: reacting racemates of chloroquine, hydroxychloroquine and analogues thereof with an acidic chiral resolution reagent to generate corresponding salts, and separating and purifying to obtain optically pure salts of chloroquine, hydroxychloroquine and analogues thereof, and reacting with alkali to obtain (R)- or (S)- chloroquine with high optical purity and (R)- or (S)- hydroxychloroquine and analogues thereof. The method is simple and convenient to operate and low in cost, the enantiomer purity can reach 99.9% ee, and industrial production of chloroquine, hydroxychloroquine and analogues thereof with single chiral configuration is easy to realize. The invention also provides (R)- or (S)- chloroquine and (R)- or (S)- hydroxychloroquine and analogues thereof, pharmaceutical compositions and uses thereof, optically activechloroquine and hydroxychloroquine and analogues thereof reduce toxic and side effects, and have better treatment effects on coronavirus, influenza virus and autoimmune diseases.

TREATMENT OR PREVENTION OF CORONAVIRIDAE INFECTION

A method of treating or preventing a Coronaviridae infection in a subject comprising administrating a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt, ester or prodrug thereof to the subject in need thereof, wherein R1 is OH or H, and the Coronaviridae comprises at least one selected from 2019-nCov virus, HCov 229E virus, SARS virus, MERS virus.

Refining method of hydroxychloroquine crude product

The present invention provides a refining method of a hydroxychloroquine crude product. The refining method comprises two refining processes. In the first refining process, by controlling the use amount of a derivatization reagent and the derivatization reaction temperature, an impurity III is converted into a new impurity easy to remove, the new impurity is removed through a recrystallization mode, the active ingredient hydroxychloroquine hardly participates in the derivatization reaction, the primary refining of the crude hydroxychloroquine product is realized, almost no impurity III exists in the primary refined product, the loss of hydroxychloroquine is low, the yield reaches 90% or above, and the purity reaches 99.5% or above. In the second refining process, a simple recrystallization mode is adopted, the yield of the hydroxychloroquine is high, the yield reaches about 95%, and the purity reaches 99.9%.

Hydroxychloroquine sulfate and preparation method thereof

The invention discloses hydroxychloroquine sulfate and a preparation method thereof, and relates to the technical field of medicinal chemistry. The preparation method comprises the steps of mixing 4, 7-dichloroquinoline with a hydroxychloroquine side chain, carrying out heating condensation in the presence of an organic base catalyst, adding water and liquid, and carrying out cooling crystallization to obtain hydroxychloroquine; and dissolving hydroxychloroquine in an ethyl acetate and ethanol aqueous solution, heating, dissolving and clarifying, dropwise adding concentrated sulfuric acid, cooling, crystallizing, filtering and drying to obtain hydroxychloroquine sulfate. The method has the beneficial effects that a solvent-free reaction is used, and a catalyst is added, so that high pollution is avoided, the reaction process is accelerated, and the operation is simple; and meanwhile, the HPLC purity of the obtained hydroxychloroquine refined product is not less than 96.50%, the maximum single impurity content is less than 0.10%, the yield can reach 85%, the HPLC purity of hydroxychloroquine sulfate is not less than 98.00%, the maximum single impurity content is less than 0.10%, and the yield can reach 90%.

Preparation method of hydroxychloroquine

The invention relates to the field of medicinal chemistry, in particular to a preparation method of hydroxychloroquine. According to the method, the nucleophilic reaction is promoted by adding the organic amine, the reaction time is shortened, the reaction conversion rate is increased, the impurity content is reduced, the product quality is improved, other organic solvents and catalysts are not used, the high-pressure reaction condition is avoided, and the method is mild in reaction condition, simple in post-treatment, high in process controllability and suitable for industrial production. The preparation method of hydroxychloroquine comprises the following step: reacting 4, 7-dichloroquinoline and 2-[(4-amino amyl) (ethyl) amino] ethanol in triethanolamine to prepare hydroxychloroquine.