246512-44-7

Basic information

• Product Name: 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide
• Synonyms: 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide;Gefitinib Impurity 6;Gefintinib Impurity 1;2-Amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)-benzamide
• CAS NO: 246512-44-7
• Molecular Formula: C₁₅H₂₃N₃O₄
• Molecular Weight: 309.36082
• Mol File: 246512-44-7.mol

Chemical Properties

• Melting Point: 153.5 °C
• Boiling Point: 460.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.208±0.06 g/cm3(Predicted)
• PKA: 15.86±0.50(Predicted)
• CAS DataBase Reference: 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide(246512-44-7)
• EPA Substance Registry System: 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide(246512-44-7)

Safety Data

• Hazardous Substances Data: 246512-44-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide is used as a potential candidate for drug development due to its unique structural features and the presence of functional groups that may impart specific pharmacological properties. Its potential applications in medicinal chemistry could include the development of new therapeutic agents targeting various diseases and conditions.
Used in Medicinal Chemistry Research:
2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide is used as a subject of research in medicinal chemistry to explore its potential biological activities and evaluate its efficacy as a therapeutic agent. 2-aMino-4-Methoxy-5-(3-Morpholinopropoxy)benzaMide's structural features and functional groups make it an interesting molecule for studying its interactions with biological targets and its potential as a lead compound in drug discovery processes.

Upstream product

• 675126-27-9 2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile 
• 7357-67-7 4-(3-chloropropyl)morpholine 
• 675126-28-0 4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 675126-26-8 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 621-59-0 isovanillin 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 861453-16-9 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide 

Downstream Products

• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 847949-49-9 O-Demethyl-Gefitinib 
• 184475-35-2 gefitinib 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 

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.

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).

AN IMPROVED PROCESS FOR THE PREPARATION OF GEFITINIB

Present invention discloses an improved process for the preparation of gefitinib (4-(3'-chloro-4'-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline), of formula-I, which comprises: (i) etherification of iso-vanillin with 3-morpholinopropyl halide, (ii) nitration using nitric acid, (iii) oximation, (iv) dehydration, (v) reduction-cum-hydrolysis, (vi) quinazolinone formation, (vii) introduction of a leaving group at C-4 position in quinozolinone, and (viii) condensation with 3-chloro4-fluoroaniline to get the crude gefitinib. Purification of crude gefitinib is achieved via acid/base treatment or by crystallization from solvents such as ethyl acetate, isopropanol, acetonitrile, and methyl ethyl ketone. Formula I, IX, XI, XIII, XV and XVI.

PROCESS FOR THE PREPARATION OF 4-(3'-CHLORO-4'-FLUOROANILINO)-7-METHOXY-6-(3-MORPHOLINOPROPOXY) QUINAZOLINE

The invention relates to chemical processes and intermediates useful in the manufacture of the quinazoline derivative 4 (3'' chloro 4'' fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline. In particular, the invention relates to processes for the manufacture of 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one of Formula (II) and 4-methoxy-5-(3-morpholinopropoxy)-2-nitrobenzonitrile of Formula (III) and their use in the manufacture of said quinazoline derivative