Mutant EGFR inhibitor

Base Information

• Chemical Name: Mutant EGFR inhibitor
• CAS No.: 1421373-62-7
• Molecular Formula: C₂₇H₃₀ClN₇O₂
• Molecular Weight: 520.034
• Mol file: 1421373-62-7.mol

Synonyms:N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide

Chemical Property of Mutant EGFR inhibitor

Chemical Property:

• PKA: 12.66±0.70(Predicted)
• Density: 1.316±0.06 g/cm3(Predicted)

Purity/Quality:

>98% ^*data from raw suppliers

MutantEGFRinhibitor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Mutant EGFR inhibitor

There total 9 articles about Mutant EGFR inhibitor 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: 69.0%

N4-(5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methylbenzene-1,2,4-triamine (1421372-61-3) + acryloyl chloride (814-68-6,25189-84-8) → N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide (1421373-62-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h; Cooling with ice;

Reference yield:

N1-(5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-N4-(2-(dimethylamino)ethyl)-2-methoxy-N4-methyl-5-nitrobenzene-1,4-diamine (1421372-62-4) → N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide (1421373-62-7)

Guidance literature:

Multi-step reaction with 2 steps

1: iron; ammonium chloride / water; ethanol / 1.5 h / Reflux

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice

With iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; water;

Reference yield:

5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)-pyrimidin-2-amine (1421372-44-2) → N-(5-((5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide (1421373-62-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 140 °C / Microwave irradiation

2: iron; ammonium chloride / water; ethanol / 1.5 h / Reflux

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice

With iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl acetamide; water;

upstream raw materials:

3-(2,5-dichloropyrimidine-4-yl)-1H-indole

4-fluoro-2-methoxy-5-nitro-phenylamine

5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)-pyrimidin-2-amine

N⁴-(5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-N¹-(2-(dimethylamino)ethyl)-5-methoxy-N¹-methylbenzene-1,2,4-triamine

Refernces

• 1、 Finlay, M. Raymond V.,Anderton, Mark,Ashton, Susan,Ballard, Peter,Bethel, Paul A.,Box, Matthew R.,Bradbury, Robert H.,Brown, Simon J.,Butterworth, Sam,Campbell, Andrew,Chorley, Christopher,Colclough, Nicola,Cross, Darren A. E.,Currie, Gordon S.,Grist, Matthew,Hassall, Lorraine,Hill, George B.,James, Daniel,James, Michael,Kemmitt, Paul,Klinowska, Teresa,Lamont, Gillian,Lamont, Scott G.,Martin, Nathaniel,McFarland, Heather L.,Mellor, Martine J.,Orme, Jonathon P.,Perkins, David,Perkins, Paula,Richmond, Graham,Smith, Peter,Ward, Richard A.,Waring, Michael J.,Whittaker, David,Wells, Stuart,Wrigley, Gail L.. "Discovery of a potent and selective EGFR inhibitor (AZD9291) of both sensitizing and T790M resistance mutations that spares the wild type form of the receptor". . p. 8249 - 8267. Retrieved 2014/12/11.