675126-26-8

Basic information

• Product Name: 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile
• Synonyms: 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile;4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile;2-Nitro-4-Methoxy-5-(3-Morpholinopropoxy)benzonitrile;4-Methoxy-2-nitro-5-(3-Morpholinopropoxy)benzonitrile;4-Methoxy-5-(3-Morpholinopropoxy)-2-Nitrobenzonitrile Gefitinib HCL InterMediates G4;Benzonitrile,4-Methoxy-5-[3-(4-Morpholinyl)propoxy]-2-nitro-;Gefitinib PI-1;-nitro-4-methoxy-5-(3-morpholinopropoxy)benzonitrile
• CAS NO: 675126-26-8
• Molecular Formula: C₁₅H₁₉N₃O₅
• Molecular Weight: 291.34554
• EINECS: 1806241-263-5
• Mol File: 675126-26-8.mol

Chemical Properties

• Melting Point: 127℃
• Boiling Point: 522.302 °C at 760 mmHg
• Flash Point: 269.679 °C
• Appearance: /
• Density: 1.29
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.96±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(675126-26-8)
• EPA Substance Registry System: 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile(675126-26-8)

Safety Data

• Hazardous Substances Data: 675126-26-8(Hazardous Substances Data)

Usage

Uses

Due to the limited data available on 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile, its specific applications are not well-defined. However, given its chemical structure and the properties of similar compounds, it can be hypothesized that it may have potential uses in various industries, such as pharmaceuticals, materials science, or chemical research. The following are potential applications based on the structure and properties of related compounds:
Used in Pharmaceutical Industry:
2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile could be used as a chemical intermediate or a building block for the synthesis of more complex molecules with potential therapeutic applications. Its unique structure may allow it to interact with biological targets in novel ways, leading to the development of new drugs.
Used in Materials Science:
In the field of materials science, 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile might be used as a component in the development of new materials with specific properties, such as improved conductivity, stability, or reactivity. Its structural features could contribute to the creation of materials with unique electronic, optical, or mechanical properties.
Used in Chemical Research:
As a novel organic compound, 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile could serve as a subject of study in chemical research, providing insights into the reactivity, stability, and potential applications of similar compounds. Researchers may use it to explore new synthetic pathways, reaction mechanisms, or to develop new analytical methods for the detection and characterization of related compounds.

Upstream product

• 929683-54-5 3-(3-chloropropoxy)-4-methoxybenzaldehyde 
• 110-91-8 morpholine 
• 1315512-61-8 C₁₁H₁₁ClN₂O₄ 
• 621-59-0 isovanillin 
• 7357-67-7 4-(3-chloropropyl)morpholine 
• 102714-71-6 4,5-dimethoxy-2-nitrobenzonitrile 
• 861453-13-6 4-methoxy-6-nitro-3-[3-(4-morpholinyl)propoxy]benzaldoxime 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 861453-11-4 4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldehyde 
• 934191-95-4 4-methoxy-3-[3-(4-morpholinyl)propoxy]benzaldoxime 
• 675126-28-0 4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile 

Downstream Products

• 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 
• 847949-49-9 O-Demethyl-Gefitinib 
• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 184475-35-2 gefitinib 
• 675126-27-9 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile 

Relevant articles and documents

4-heterocycle substituted quinazoline derivative and preparation method and application thereof

The invention discloses a 4-heterocycle substituted quinazoline derivative and a preparation method and application thereof. The compound has a structure expressed by a general formula (I): (please see the specification for the formula), in the formula, R1 and R2 are independently selected from hydrogen, a saturated or unsaturated five-membered heterocycle, or a saturated or unsaturated six-membered heterocycle, and n is an integer from 1 to 6; X is NH, O or S; and a heterocycle A is independently selected from pyridine or substituted pyridine, pyrimidine or substituted pyrimidine, pyrazol orsubstituted pyrazol, pyrazine or substituted pyrazine, thiazole or substituted thiazole, or benzothiazole or substituted benzothiazole. The compound or pharmaceutically formable salts thereof have aninhibitory effect on proliferation of tumor cells and can be used for preparing drugs for treatment of glioma, non-small cell lung cancer, breast cancer, colon cancer, stomach cancer, liver cancer andcervical cancer diseases.

Design, synthesis, and biological evaluation of quinazoline derivatives containing piperazine moieties as antitumor agents

A series of novel quinazoline derivatives containing piperazine analogs are synthesized via substitution reactions with 6,7-disubstituted 4-chloroquinazoline and benzyl piperazine (amido piperazine). Potent antiproliferative activities are observed against A549, HepG2, K562, and PC-3 with N-(3-chlorophenyl)-2-(4-(7-methoxy-6-(3-morpholino-propoxy)quinazoline-4-yl)piperazine-1-yl)acetamidename C9 showing excellent activity. This active derivative was screened for cell migration ability, proliferation effects, and apoptosis against A549 and PC-3 cells, with the result showing biological activity almost equal to that of the control gefitinib.

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.

A high-purity of gefitinib preparation method

The invention relates to a process for preparing high-purity of gefitinib method the method comprises the following 5 steps: 1st step exotic fragrance orchid [...], 2nd step etherification, 3rd step nitration, step reduction 4th, 5th step ring gathers passes through purification of the final product is obtained. The programme raw material sources are extensive, the cost is reduced, improving the quality of products, it is easy to further popularization and application.

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.

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%.

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.

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.

One-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones and synthesis of gefitinib and erlotinib hydrochloride

A simple and efficient one-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones involving reduction, formylation, hydrolysis and cyclization is reported. These quinazolinones have been used for making in economical way the anticancer drug molecules gefitinib (Iressa) and erlotinib HCl (Tarceva).

Synthesis of [11C]Iressa as a new potential PET cancer imaging agent for epidermal growth factor receptor tyrosine kinase

Iressa (Gefitinib) is an orally active inhibitor of epidermal growth factor receptor tyrosine kinase (EGFR-TK) involved in cell signal transduction processes critical to proliferation, apoptosis, repair, and angiogenesis of cancer cells. [11C]Iressa was first designed and synthesized as a new potential positron emission tomography (PET) cancer imaging agent for EGFR-TK in 30-40% radiochemical yield with 4.0-6.0 Ci/μmol specific activity at end of bombardment (EOB).