CX-5461

Base Information

• Chemical Name: CX-5461
• CAS No.: 1138549-36-6
• Molecular Formula: C27H27N7O2S
• Molecular Weight: 513.623
• Mol file: 1138549-36-6.mol

Synonyms:CX-5461;2-(4-Methyl-1,4-diazepan-1-yl)-N-((5-Methylpyrazin-2-yl)Methyl)-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxaMide

Chemical Property of CX-5461

Chemical Property:

• Boiling Point: 739.9±60.0 °C at 760 mmHg
• PKA: 8.53±0.20(Predicted)
• Flash Point: 401.3±32.9 °C
• PSA: 123.97000
• Density: 1.5±0.1 g/cm³
• LogP: 3.62650
• Storage Temp.: +2C to +8C
• Solubility.: insoluble in H2O; insoluble in EtOH; insoluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

RNA Polymerase I Inhibitor II, CX-5461 - CAS 1138549-36-6 - Calbiochem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CX-5461

There total 6 articles about CX-5461 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: 87.0%

ethyl 2-(4-methyl-1,4-diazepan-1-yl)-5-oxo-5H-benzo[4,5]thiazolo-[3,2-a][1,8]-naphthyridine-6-carboxylate (1138555-04-0) + (5-methylpyrazine-2-yl)methylamine (132664-85-8) → 2-(4-methyl-1,4-diazepan-1-yl)-N-((5-methylpyrazin-2-yl)methyl)-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxamide (1138549-36-6)

Guidance literature:

With aluminum (III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2010.12.108

Reference yield: 66.0%

C23H24N4O3S*ClH + (5-methylpyrazine-2-yl)methylamine (132664-85-8) → 2-(4-methyl-1,4-diazepan-1-yl)-N-((5-methylpyrazin-2-yl)methyl)-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxamide (1138549-36-6)

Guidance literature:

C₂₃H₂₄N₄O₃S*ClH; In dichloromethane; at 30 ℃; for 0.166667h; Large scale;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 30 ℃; for 0.166667h; Large scale;

(5-methylpyrazine-2-yl)methylamine; Further stages; Large scale;

Reference yield:

ethyl 2-chloro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate (881633-93-8) → 2-(4-methyl-1,4-diazepan-1-yl)-N-((5-methylpyrazin-2-yl)methyl)-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxamide (1138549-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetonitrile / 4 h / Reflux

2.1: aluminum (III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / -5 - 5 °C

2.2: 1 h / -5 - 20 °C

With aluminum (III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;

DOI:10.1021/ml300110s

upstream raw materials:

ethyl 2-(4-methyl-1,4-diazepan-1-yl)-5-oxo-5H-benzo[4,5]thiazolo-[3,2-a][1,8]-naphthyridine-6-carboxylate

(5-methylpyrazine-2-yl)methylamine

ethyl 2-chloro-5-oxo-5H-benzo[4,5]thiazolo[3,2-a][1,8]naphthyridine-6-carboxylate

2,6-dichloropyridine-3-carboxylic acid

Refernces

• 1、 Haddach, Mustapha,Schwaebe, Michael K.,Michaux, Jerome,Nagasawa, Johnny,O'Brien, Sean E.,Whitten, Jeffrey P.,Pierre, Fabrice,Kerdoncuff, Pauline,Darjania, Levan,Stansfield, Ryan,Drygin, Denis,Anderes, Kenna,Proffitt, Chris,Bliesath, Josh,Siddiqui-Jain, Adam,Omori, May,Huser, Nanni,Rice, William G.,Ryckman, David M.. "Discovery of CX-5461, the first direct and selective inhibitor of RNA polymerase I, for cancer therapeutics". supporting information; experimental part. p. 602 - 606. Retrieved 2012/10/08.
• 2、 -. "QUINOLONE ANALOGS AND METHODS RELATED THERETO". Page/Page column 86. . Retrieved 2009/04/24.