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Water → 5-(4-aminobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

HRID 1736210
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1736210
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]2[C:15](=[O:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:21]([F:32])[CH:20]=3)[O:18][C:13]=2[C:12]([F:34])=[CH:11][C:10]=1[F:35])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>O1CCCC1>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]2[C:15](=[O:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:28])[CH3:29])=[C:21]([F:32])[CH:20]=3)[O:18][C:13]=2[C:12]([F:34])=[CH:11][C:10]=1[F:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 194347955-(4-azidobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

Produkt 1

HCID 194348645-(4-aminobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

332 mg (0.682 mmol) of the above 5-(4-azidobutylamino)-6, 8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was dissolved in 20 mL of tetrahydrofuran, 272 mg (1.02 mmol) of triphenylphosphine and 20 mL of water were added and the mixture was stirred at room temperature for 22 hours. Ethyl acetate was added to the reaction solution, and the organic layer was separated, washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1-chloroform:methanol:aqueous ammonia=9:1:1) to give 260 mg of 5-(4-aminobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 83%).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1-chloroform:methanol:aqueous ammonia=9:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b932d6e270a64ca789c478e29e2d7ebe
Quelldatensatz
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05539112

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