Brequinar

Base Information

• Chemical Name: Brequinar
• CAS No.: 96187-53-0
• Molecular Formula: C₂₃H₁₅F₂NO₂
• Molecular Weight: 375.374
• Hs Code.: 2933499090
• UNII: 5XL19F49H6
• DSSTox Substance ID: DTXSID00242165
• Nikkaji Number: J332.223H
• Wikipedia: Brequinar
• Wikidata: Q27075486
• NCI Thesaurus Code: C1560
• Pharos Ligand ID: 39YFT4F4H76M
• Metabolomics Workbench ID: 148035
• ChEMBL ID: CHEMBL38434
• Mol file: 96187-53-0.mol

Synonyms:6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic acid;6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium;brequinar;brequinar potassium;brequinar sodium;brequinar sodium salt;DuP 785;DuP-785;NSC 368390;NSC-368390

Chemical Property of Brequinar

Chemical Property:

• Vapor Pressure: 5.71E-13mmHg at 25°C
• Melting Point: 355-357℃ (N,N-dimethylformamide water )
• Refractive Index: 1.644
• Boiling Point: 550.9 °C at 760 mmHg
• PKA: pKa 4.45(H2O t=RT I=0.10) (Uncertain)
• Flash Point: 287 °C
• PSA: 50.19000
• Density: 1.319 g/cm³
• LogP: 5.85360
• Storage Temp.: 2-8°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 375.10708505
• Heavy Atom Count: 28
• Complexity: 551

Purity/Quality:

99% ^*data from raw suppliers

Brequinar >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)O
• Recent ClinicalTrials: CRISIS2: A Phase 2 Study of the Safety and Antiviral Activity of Brequinar in Non-hospitalized Pts With COVID-19
• Uses: Antineoplastic.

Technology Process of Brequinar

There total 5 articles about Brequinar 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: 55.0%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 1-(2′-fluoro-[1,1′-biphenyl]-4-yl)propan-1-one (37989-92-7) → brequinar (96187-53-0)

Guidance literature:

5-fluoro-1H-indole-2,3-dione; With potassium hydroxide; In ethanol; water; at 20 ℃; for 0.25h; Inert atmosphere;

1-(2′-fluoro-[1,1′-biphenyl]-4-yl)propan-1-one; In ethanol; water; for 12h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201702999

Reference yield:

5-fluoro-1H-indole-2,3-dione (443-69-6) + diethyl ether (60-29-7,927820-24-4) + 1-(2′-fluoro-[1,1′-biphenyl]-4-yl)propan-1-one (37989-92-7) → brequinar (96187-53-0)

Guidance literature:

With potassium hydroxide; In ethanol; water;

Reference yield:

4'-Bromopropiophenone (10342-83-3) → brequinar (96187-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; dipotassium hydrogenphosphate / water; 1,4-dioxane / 1.5 h / 130 °C / Sealed tube; Inert atmosphere

2.1: potassium hydroxide / ethanol; water / 0.25 h / 20 °C / Inert atmosphere

2.2: 12 h / Inert atmosphere; Reflux

With dipotassium hydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hydroxide; In 1,4-dioxane; ethanol; water; 2.1: |Pfitzinger Quinoline Synthesis / 2.2: |Pfitzinger Quinoline Synthesis;

DOI:10.1002/chem.201702999

upstream raw materials:

5-fluoro-1H-indole-2,3-dione

diethyl ether

1-(2′-fluoro-[1,1′-biphenyl]-4-yl)propan-1-one

4'-Bromopropiophenone

Refernces

• 1、 -. "COMPOUNDS AND METHODS USEFUL FOR TREATING OR PREVENTING HEMATOLOGICAL CANCERS". Page/Page column 54; 55. . Retrieved 2017/03/28.
• 2、 -. "4-Quinoline carboxylic acid derivatives useful as immunosuppressive agents". . . Retrieved 2008/06/13.