O-Desmethyl Gefitinib

Base Information

• Chemical Name: O-Desmethyl Gefitinib
• CAS No.: 847949-49-9
• Molecular Formula: C21H22 Cl F N4 O3
• Molecular Weight: 432.882
• Hs Code.: 29349990
• Mol file: 847949-49-9.mol

Synonyms:M523595;4-[(3-Chloro-4-fluorophenyl)amino]-6-[3-(4-morpholinyl)propoxy]-7-quinazolinol;O-Desmethyl Gefitinib

Chemical Property of O-Desmethyl Gefitinib

Chemical Property:

• Vapor Pressure: 2.68E-15mmHg at 25°C
• Melting Point: 117-120?C
• Refractive Index: 1.65
• Boiling Point: 606.4°C at 760 mmHg
• Flash Point: 320.5°C
• PSA: 79.74000
• Density: 1.386g/cm³
• LogP: 3.98350
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

O-Desmethyl Gefitinib ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: O-Desmethyl Gefitinib-d8 is the isotope labelled analog of O-Desmethyl Gefitinib (D291680); a major metabolite of Gefitinib (G304000) which is an antineoplastic. A major metabolite of Gefitinib

Technology Process of O-Desmethyl Gefitinib

There total 16 articles about O-Desmethyl Gefitinib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

gefitinib (184475-35-2) → O-Demethyl-Gefitinib (847949-49-9)

Guidance literature:

With pyridine hydrochloride; at 170 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.08.123

Reference yield: 63.6%

C28H28ClFN4O3 → O-Demethyl-Gefitinib (847949-49-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; for 6h;

DOI:10.1016/j.bmcl.2016.10.084

Reference yield:

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile (675126-28-0) → O-Demethyl-Gefitinib (847949-49-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / aq. H₂SO₄; HNO₃; AcOH / 50 h / 20 °C

2.1: 75 percent / sodium dithionite / H₂O / 20 - 50 °C

3.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C

4.1: formamide / 20 - 100 °C

4.2: 78 percent / 7 h / 100 °C

5.1: 90 percent / POCl₃; triethylamine / toluene / 24 h / 58 °C

6.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating

7.1: 54 percent / LiCl / dimethylformamide / 15 h / Heating

With potassium hydroxide; sodium dithionite; sulfuric acid; nitric acid; formamide; acetic acid; triethylamine; lithium chloride; trichlorophosphate; In tert-Amyl alcohol; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1016/j.bmcl.2006.04.080

upstream raw materials:

gefitinib

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

4-(3-chloropropyl)morpholine

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile

Refernces

• 1、 Yamahana, Hirari,Kunieda, Yukari,Tominaga, Masahide,Yamada, Hisatsugu,Uto, Yoshihiro. "Development of a novel acetyl glucose-modified gefitinib derivative to enhance the radiosensitizing effect". . . Retrieved 2021.
• 2、 -. "Fluorescent probe based on small molecule inhibitor as well as preparation method and application thereof". Paragraph 0053-0055. . Retrieved 2020/09/20.