N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine

Base Information

• Chemical Name: N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine
• CAS No.: 1393112-45-2
• Molecular Formula: C₂₉H₂₆ClFN₄O₄S
• Molecular Weight: 581.067
• Mol file: 1393112-45-2.mol

Synonyms:N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine

Chemical Property of N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-Desfluoro2-FluoroLapatinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Desfluoro 2-Fluoro Lapatinib is a compound related to drug Lapatinib (L175808), which is a selective inhibitor of epidermal growth factor receptor (EGFR) and HER-2 tyrosine kinases. Lapatinib is used to treat breast cancer, especially metastatic breast cancer that has progressed after trastuzumab treatment and other chemotherapy.

Technology Process of N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine

There total 7 articles about N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine 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:

5-[4-({3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}amino)quinazoline-6-yl]furan-2-carbaldehyde (1393112-44-1) + 2-(methylsulfonyl)ethylamine hydrochloride (104458-24-4) → N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine (1393112-45-2)

Guidance literature:

5-[4-({3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}amino)quinazoline-6-yl]furan-2-carbaldehyde; 2-(methylsulfonyl)ethylamine hydrochloride; With sodium tris(acetoxy)borohydride; acetic acid; diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 - 35 ℃; for 3h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

5-formylfurane-2-boronic acid (27329-70-0) → N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine (1393112-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / palladium diacetate / ethanol; tetrahydrofuran / 1 h / 75 °C / Inert atmosphere

2: diisopropylamine; acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 - 35 °C / Inert atmosphere

With sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; diisopropylamine; palladium diacetate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

Reference yield:

2-chloro-4-nitrophenol (619-08-9) → N-{3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazoline-4-amine (1393112-45-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetonitrile / 2 h / 60 °C / Inert atmosphere

2.1: iron; ammonium chloride; water / ethanol; methanol / 2 h / 68 °C / Inert atmosphere

3.1: isopropyl alcohol / 2 h / 70 °C / Inert atmosphere

4.1: potassium carbonate; palladium diacetate / ethanol; tetrahydrofuran / 1 h / 75 °C / Inert atmosphere

5.1: acetic acid; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 35 °C / Inert atmosphere

5.2: 2 h / 25 °C / Inert atmosphere

With water; palladium diacetate; iron; potassium carbonate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

upstream raw materials:

5-formylfurane-2-boronic acid

5-[4-({3-chloro-4-[(2-fluorobenzyl)oxy]phenyl}amino)quinazoline-6-yl]furan-2-carbaldehyde

2-(methylsulfonyl)ethylamine hydrochloride

2-chloro-1-[(2-fluorobenzyl)oxy]-4-nitrobenzene

Refernces

• 1、 -. "Impurity of lapatinib and salts thereof". . . Retrieved 2012/09/10.