Potassium Carbonate → Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonate

HRID 1476710

Reaktionsgleichung

Reaktionsgleichung von HRID 1476710
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:35]([O:38][P:39]([CH2:45]Br)(=[O:44])[O:40][CH:41]([CH3:43])[CH3:42])([CH3:37])[CH3:36]>CC#N>[CH:41]([O:40][P:39]([CH2:45][NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:3]=1[C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])(=[O:44])[O:38][CH:35]([CH3:37])[CH3:36])([CH3:43])[CH3:42]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 4366885Diisopropyl bromomethylphosphonateHCID 718115872-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl-thio)benzamide

Produkt 1

HCID 71811718Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Compound 25 (1.0 equiv.) was dissolved in MeCN (40 mL) and treated with anhydrous potassium carbonate (2.0 equiv.) at room temperature. To this mixture diisopropyl(bromomethyl)phosphonate (1.2 equiv.) was added via a micro syringe. After being stirred for 4 Hours at 60° C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted by ethyl acetate (50 mL), and washed with water (2×10 mL). Then it was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid (235.2 mg, 41% yield).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe crude residue was diluted by ethyl acetate (50 mL)
  3. washwashed with water (2×10 mL)
  4. dry with materialThen it was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-88db3d8f35ff41cca758454c7100483a
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09402819B2

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