3-Acridinecarboxamide, 2-fluoro-9,10-dihydro-N-[1-methyl-1-[3-(methylthio)phenyl]ethyl]-9-oxo-

Base Information

• Chemical Name: 3-Acridinecarboxamide, 2-fluoro-9,10-dihydro-N-[1-methyl-1-[3-(methylthio)phenyl]ethyl]-9-oxo-
• CAS No.: 566158-69-8
• Molecular Formula: C24H21FN2O2S
• Molecular Weight: 420.507
• Mol file: 566158-69-8.mol

Synonyms:

Chemical Property of 3-Acridinecarboxamide, 2-fluoro-9,10-dihydro-N-[1-methyl-1-[3-(methylthio)phenyl]ethyl]-9-oxo-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Acridinecarboxamide, 2-fluoro-9,10-dihydro-N-[1-methyl-1-[3-(methylthio)phenyl]ethyl]-9-oxo-

There total 6 articles about 3-Acridinecarboxamide, 2-fluoro-9,10-dihydro-N-[1-methyl-1-[3-(methylthio)phenyl]ethyl]-9-oxo- 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: 59.0%

2-fluoro-9-oxo-9,10-dihydro-acridine-3-carboxylic acid (566158-08-5) + 1-methyl-1-(3-methylthiophenyl)ethyl-amine → 2-fluoro-N-(2-(3-(methylthio)phenyl)propan-2-yl)-9-oxo-9,10-dihydroacridine-3-carboxamide (566158-69-8)

Guidance literature:

With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm070299x

Reference yield:

1,4-dimethyl 2-fluorobenzene-1,4-dicarboxylate (5292-47-7) → 2-fluoro-N-(2-(3-(methylthio)phenyl)propan-2-yl)-9-oxo-9,10-dihydroacridine-3-carboxamide (566158-69-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / nitric acid; sulfuric acid / 0.25 h / 0 °C

2: 90 percent / H₂ / Pd/C / ethyl acetate / 1 h

3: 80 percent / (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate; palladium(II) acetate / toluene / 24 h / 90 °C

4: 100 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 0.5 h / 75 °C

5: 84 percent / polyphosphoric acid / 0.17 h / 165 °C

6: 59 percent / triethylamine; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride / dimethylformamide / 20 °C

With lithium hydroxide; PPA; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; sulfuric acid; hydrogen; nitric acid; palladium diacetate; caesium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 3: Buchwald-Hartwig coupling;

DOI:10.1021/jm070299x

Reference yield:

2-fluoro-5-nitro-terephthalic acid dimethyl ester (5292-48-8) → 2-fluoro-N-(2-(3-(methylthio)phenyl)propan-2-yl)-9-oxo-9,10-dihydroacridine-3-carboxamide (566158-69-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / H₂ / Pd/C / ethyl acetate / 1 h

2: 80 percent / (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate; palladium(II) acetate / toluene / 24 h / 90 °C

3: 100 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 0.5 h / 75 °C

4: 84 percent / polyphosphoric acid / 0.17 h / 165 °C

5: 59 percent / triethylamine; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride / dimethylformamide / 20 °C

With lithium hydroxide; PPA; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; hydrogen; palladium diacetate; caesium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2: Buchwald-Hartwig coupling;

DOI:10.1021/jm070299x

upstream raw materials:

2-fluoro-9-oxo-9,10-dihydro-acridine-3-carboxylic acid

2-fluoro-5-phenylamino-terephthalic acid

2-fluoro-5-phenylamino-terephthalic acid dimethyl ester

1,4-dimethyl 2-fluorobenzene-1,4-dicarboxylate