BenzaMide, N-[4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-diMethoxy-2-nitro-

Base Information

• Chemical Name: BenzaMide, N-[4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-diMethoxy-2-nitro-
• CAS No.: 1024592-54-8
• Molecular Formula: C₂₈H₃₁N₃O₇
• Molecular Weight: 521.57
• Mol file: 1024592-54-8.mol

Synonyms:N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxy-2-nitro-benzamide

Chemical Property of BenzaMide, N-[4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-diMethoxy-2-nitro-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

N-[4-[2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-dimethoxy-2-nitrobenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-[4-[2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-dimethoxy-2-nitrobenzamide is an intermediate in the synthesis of Tariquidar (T007600), a P-glycoprotein drug efflux pump inhibitor that is potentially used in cancer patients.

Technology Process of BenzaMide, N-[4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-diMethoxy-2-nitro-

There total 6 articles about BenzaMide, N-[4-[2-(3,4-dihydro-6,7-diMethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-4,5-diMethoxy-2-nitro- 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: 66.0%

4,5-dimethoxy-2-nitrobenzoyl chloride (29568-78-3) + 4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolyl)ethyl>benzenamine (82925-02-8) → N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxy-2-nitro-benzamide (1024592-54-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1016/j.bmc.2009.01.072

Reference yield:

4,5-dimethoxy-2-nitro-benzoic acid (4998-07-6) + 4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolyl)ethyl>benzenamine (82925-02-8) → N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxy-2-nitro-benzamide (1024592-54-8)

Guidance literature:

With thionyl chloride; triethylamine; In tetrahydrofuran;

Reference yield:

4,5-dimethoxy-2-nitro-benzoic acid (4998-07-6) → N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxy-2-nitro-benzamide (1024592-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 83 °C

2: sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C

With thionyl chloride; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2015.06.049

upstream raw materials:

4,5-dimethoxy-2-nitrobenzoyl chloride

4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolyl)ethyl>benzenamine

4,5-dimethoxy-2-nitro-benzoic acid

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

2-amino-N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxybenzamide

Refernces

• 1、 Li, Xu-Qin,Wang, Lin,Lei, Yan,Hu, Tao,Zhang, Fei-Long,Cho, Chi-Hin,To, Kenneth K.W.. "Reversal of P-gp and BCRP-mediated MDR by tariquidar derivatives". . p. 560 - 572. Retrieved 2015/07/28.
• 2、 -. "NOVEL P-GLYCOPROTEIN INHIBITOR, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME". Page/Page column 14-15. . Retrieved 2008/06/13.