1-Iodohexane → 2-[4-[N-acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-one

HRID 1736112

Reaktionsgleichung

Reaktionsgleichung von HRID 1736112
[C:1]([N:4]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]3[C:35]([F:36])=[CH:34][C:33]([F:37])=[C:32]([NH2:38])[C:28]=3[C:29](=[O:31])[CH:30]=2)=[CH:21][C:20]=1[F:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])(=[O:3])[CH3:2].I[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([N:4]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]3[C:35]([F:36])=[CH:34][C:33]([F:37])=[C:32]([NH:38][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:28]=3[C:29](=[O:31])[CH:30]=2)=[CH:21][C:20]=1[F:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 153469942-[4-[N-Acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Produkt 1

HCID 194348532-[4-[N-acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-oneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

450 mg of Compound 28 was dissolved in 15 ml of dimethylformamide, 0.62 ml of 1-iodohexane and 34 mg of sodium hydride (60% oil dispersion) were added under ice-cooling and the mixture was stirred at room temperature for 2 hours. An aqueous solution of ammonium chloride was added, the reaction solution was concentrated under reduced pressure and the residue was extracted once with chloroform. The chloroform layer was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:1-1:3) to give 184 mg (35%) of Compound 31.

Aufarbeitung

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. extractionthe residue was extracted once with chloroform
  4. washThe chloroform layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-11a3c305d37d4c018bdc7b9eb71573db
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539112

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