675126-27-9

Basic information

• Product Name: 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile
• Synonyms: Gefitinib InterMediate;3-Methoxy-4-(3-(piperidin-1-yl)propoxy)benzonitrile;5-Methoxy-2-nitro-4-(3-(piperidin-1-yl)propoxy)benzonitrile;Benzonitrile,2-aMino-4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-;Gefitinib PI-2;2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzonitrile
• CAS NO: 675126-27-9
• Molecular Formula: C₁₅H₂₁N₃O₃
• Molecular Weight: 291
• EINECS: 1806241-263-5
• Mol File: 675126-27-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 88℃
• Boiling Point: 497.986 °C at 760 mmHg
• Flash Point: 254.973 °C
• Appearance: /
• Density: 1.21
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.08±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile(675126-27-9)
• EPA Substance Registry System: 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile(675126-27-9)

Safety Data

• Hazardous Substances Data: 675126-27-9(Hazardous Substances Data)

Usage

General Description

2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile is a chemical compound with the molecular formula C15H19N3O3. It is a nitrile derivative that contains an amine, methoxy, and morpholine functional group. 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile is used in the pharmaceutical industry for the synthesis of various pharmaceutical drugs. It has been studied for its potential antiproliferative and anticancer properties, and it has shown to inhibit the growth of certain cancer cells. Additionally, it has also been investigated for its anti-inflammatory and analgesic effects. Overall, 2-Amino-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile is a versatile chemical compound with potential applications in the development of new pharmaceutical drugs.

Upstream product

• 102714-71-6 4,5-dimethoxy-2-nitrobenzonitrile 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 621-59-0 isovanillin 
• 675126-28-0 4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 7357-67-7 4-(3-chloropropyl)morpholine 
• 675126-26-8 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile 

Downstream Products

• 184475-35-2 gefitinib 
• 1603814-04-5 N-(4-chloro-3-fluorophenyl )-7-methoxy-6-(3-morpholinopropoxy)quinazolin-4-amine 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 
• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 246512-44-7 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide 

Relevant articles and documents

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Efficient preparation method of gefitinib

The invention provides an efficient preparation method of gefitinib. 2-nitro-4,5-dimethoxybenzonitrile is used as a starting material and subjected to a demethylation reaction, a substitution reaction, a nitro reduction reaction, a ring forming reaction, an amino substitution reaction and the like to obtain a finished gefitinib product. By means of the preparation method, gefitinib with the purityhigher than 99.9% can be obtained, the total yield of the preparation method is 61-75%, raw materials used in the method are low in price, there are only five steps in the process route, the operation is simple and easy to control, the yield of the target product is high, and the repeatability is good.

Design, synthesis, and antitumor activity of novel quinazoline derivatives

In an attempt to explore a new class of epidermal growth factor receptor (EGFR) inhibitors, novel 4-stilbenylamino quinazoline derivatives were synthesized through a Dimorth rearrangement reaction and characterized via IR, 1H-NMR, 13C-NMR, and HRMS. Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. These synthesized compounds were evaluated for antitumor activity in vitro against eight human tumor cell lines with an MTS assay. Most synthesized compounds exhibited more potent activity (IC50 = ~2.0 μM) than gefitinib (IC50 > 10.0 μM) against the A431, A549, and BGC-823 cell lines. Docking methodology of compound 6c and 6i binding into the ATP site of EGFR was carried out. The results showed that fluorine and trifluoromethyl played an important role in efficient cell activity.