(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide

Base Information

• Chemical Name: (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
• CAS No.: 473727-83-2
• Molecular Formula: C21H23N3O5
• Molecular Weight: 397.431
• Mol file: 473727-83-2.mol

Synonyms:3-[[3-[(Dimethylamino)carbonyl]-2-hydroxyphenyl]amino]-4-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]cyclobut-3-ene-1,2-dione;

Chemical Property of (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide

Chemical Property:

• Melting Point: 118-120 °C
• Boiling Point: 548.67 °C at 760 mmHg
• PKA: 7.93±0.50(Predicted)
• Flash Point: 285.626 °C
• PSA: 111.88000
• Density: 1.346 g/cm³
• LogP: 2.97550
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Sch527123 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sch 527123 is a potent CXCR2 antagonist. It can potentially inhibits human colon cancer liver metastasis.

Technology Process of (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide

There total 14 articles about (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide 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: 90.0%

(R)-1-(5-methylfuran-2-yl)propan-1-amine (473732-94-4) + 3-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide (464913-33-5) → squaramide (473727-83-2)

Guidance literature:

In ethanol; at 20 ℃;

DOI:10.1021/jm0609622

Reference yield: 83.0%

3-amino-2-hydroxy-N,N-dimethylbenzamide (464913-11-9) + 3-ethoxy-4-[1-(5-methylfuran-2-yl)propylamino]cyclobut-3-en-1,2-dione (473733-74-3) → squaramide (473727-83-2)

Guidance literature:

potassium carbonate; In ethanol; at 60 ℃; for 3.5h; Product distribution / selectivity;

Reference yield: 77.6%

3-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide (464913-33-5) + (R)-1-(5-methylfuran-2-yl)propylamine para-toluenesulfonate → squaramide (473727-83-2)

Guidance literature:

With triethylamine; In acetonitrile; at 40 - 70 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

(R)-1-(5-methylfuran-2-yl)propan-1-amine

3-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide

3-amino-2-hydroxy-N,N-dimethylbenzamide

5-Methylfurfural

Downstream raw materials:

C₂₁H₂₃N₃O₅*H₂O

Refernces

• 1、 -. "PROCESS AND INTERMEDIATES FOR THE SYNTHESIS OF 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS". Page/Page column 33-34. . Retrieved 2009/03/07.
• 2、 -. "Synthesis of 2-hydroxy-N,N-dimethyl-3-[[2-[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-l]aminobenzamide". Page/Page column 24-25. . Retrieved 2008/06/13.