675126-28-0

Basic information

• Product Name: 3-(3-morpholinylpropoxy)-4-methoxybenzonitrile
• Synonyms: 4-Methoxy-3-(3-(Morpholin-3-yl)propoxy)benzonitrile;4-Methoxy-3-[3-(4-morpholinyl)propoxy]benzonitrile;3-(3-morpholinylpropoxy)-4-methoxybenzonitrile
• CAS NO: 675126-28-0
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.3309
• Product Categories: Gefitinib
• Mol File: 675126-28-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 52.4 °C
• Boiling Point: 436.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 7.10±0.10(Predicted)
• CAS DataBase Reference: 3-(3-morpholinylpropoxy)-4-methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-morpholinylpropoxy)-4-methoxybenzonitrile(675126-28-0)
• EPA Substance Registry System: 3-(3-morpholinylpropoxy)-4-methoxybenzonitrile(675126-28-0)

Safety Data

• Hazardous Substances Data: 675126-28-0(Hazardous Substances Data)

Usage

General Description

3-(3-morpholinylpropoxy)-4-methoxybenzonitrile, also known as the chemical compound SB-649868, is a potent and selective antagonist for the orexin OX1 and OX2 receptors, which are involved in the regulation of wakefulness and sleep. 3-(3-morpholinylpropoxy)-4-methoxybenzonitrile has been studied for its potential use in the treatment of various sleep disorders and has shown promising results in preclinical trials. It is a member of the benzonitrile class of compounds and has a molecular formula of C17H20N2O3. Its specific mechanism of action involves blocking the binding of orexin to its receptors, ultimately leading to a promotion of sleep. Further research and clinical trials are being conducted to investigate the potential therapeutic applications of this compound.

Upstream product

• 934191-95-4 4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime 
• 4441-30-9 3-morpholin-4-ylpropan-1-ol 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 1018895-28-7 methanesulfonic acid 3-morpholin-4-yl-propyl ester 
• 861453-11-4 4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde 
• 621-59-0 isovanillin 
• 7357-67-7 4-(3-chloropropyl)morpholine 

Downstream Products

• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 184475-35-2 gefitinib 
• 861453-16-9 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 
• 246512-44-7 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide 
• 675126-27-9 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile 
• 847949-49-9 O-Demethyl-Gefitinib 
• 675126-26-8 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile 

Relevant articles and documents

Preparing method of gefitinib intermediate

The invention discloses a preparing method of a gefitinib intermediate. The method includes the following steps of firstly, making a compound 1 react in the presence of sodium formate, formic acid andhydroxylamine sulphate to obtain a compound 2; secondly, making the compound 2 and a compound 3 react in the presence of potassium carbonate in a first solvent to obtain a compound 4; thirdly, makingthe compound 4 react in the presence of sulfuric acid and nitric acid in a second solvent to obtain a compound 5; fourthly, making the compound 5 react in the presence of alkaline and hydrogen peroxide in a third solvent to obtain a compound 6; fifthly, making the compound 6 react in the presence of ammonium formate and palladium/carbon in a fourth solvent to obtain a compound 7; sixthly, makingthe compound 7 react in the presence of formic acid and formamide to obtain a compound 8.

New synthesis method of gefitinib

The invention relates to a new synthetic method of an anti-tumor drug 4-(3-chloro-4-fluorophenylamino)-7-methoxy-6-(3-morpholinylpropoxy)quinazoline (gefitinib, I). According to the synthesis method,synthesis is performed through a novel synthetic intermediate. Before a quinazoline mother ring is synthesized, hydroxy of 3-hydroxy-4-methoxybenzonitrile is reacted with 3-morpholinopropyl chloride firstly, so that the steps of adding protecting groups and removing the protecting groups are reduced, the synthesis route is shortened, the step number of synthesis is lowered, raw materials are cheapand easily obtained, the use of chlorinated reagents which heavily pollute the environment is avoided, the purification process is simplified, the pH (potential of hydrogen) value does not need to berepeatedly adjusted, the operation is safe and simple, and the reaction yield exceeds 60%.

Synthetic method of 4-(3-chlorine-4-fluorophenyl)-7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline

The invention discloses a synthetic method of 4-(3-chlorine-4-fluorophenyl)-7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline. The synthetic method comprises the following steps that 3-hydroxy-4-methoxy benzonitrile serves as the raw material and reacts with 3-chloropropyl morpholine, and 4-methoxyl-3-[3-(4-morpholinyl) propoxy] cyanobenzene is obtained; the 4-methoxyl-3-[3-(4-morpholinyl) propoxy] cyanobenzene is nitrified with mixed acid, and 2-nitryl-4-methoxyl-5-[3-(4-morpholinyl) propoxy] cyanobenzene is obtained; the 2-nitryl-4-methoxyl-5-[3-(4-morpholinyl) propoxy] cyanobenzene is subjected to reduction, and then 2-amino-4-methoxyl-5-[3-(4-morpholinyl) propoxy] cyanobenzene is obtained; 3-chlorine-4-fluoroaniline reacts with an imine complex, N'-(3-chlorine-4-phenyl)-N, N-dimethyl formamidine is obtained, and the imine complex is prepared from DMF and dimethyl sulfate through heating and a reaction; 2-amino-4-methoxyl-5-[3-(4-morpholinyl) propoxy] cyanobenzene reacts with the N'-(3-chlorine-4-fluorophenyl)-N, N-dimethyl formamidine, so that the 4-(3-chlorine-4-fluorophenyl)-7-methoxyl-6-[3-(4-morpholinyl) propoxy] quinazoline is obtained. The synthetic method has the advantages of being environmentally friendly and high in yield.