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Dimethylformamide → HCID 86603473, Verbindung

HRID 2426273
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2426273
C([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][CH2:18][CH:19]=[CH:20][C:13]2=[N:12][C:11]=1[C:21]([O:23]C)=O)(=O)C1C=CC=CC=1.CC[N:27]([CH:31](C)C)C(C)C.[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1.C(N(CC)CC)C.CN([CH:53]=[O:54])C>>[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:21]([C:11]2[N:12]=[C:13]3[CH2:20][CH:19]([N:27]([O:54][CH3:53])[CH3:31])[CH2:18][CH2:17][N:14]3[C:15](=[O:16])[C:10]=2[OH:9])=[O:23])=[CH:37][CH:36]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 67148094HCID 67148094, Verbindung

Produkt 1

HCID 86603473HCID 86603473, Verbindung

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of methyl 3-(benzoyloxy)-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate in anhydrous DMF were added O, N-dimethylhydroxylamine hydrochloride (2.5 eq.) and DIPEA (2.2 eq.). The mixture was stirred and warmed to 65° C. for 6 h. The mixture was cooled to room temperature and the solvent was removed under high vacuum. The residue was dissolved in methanol and p-fluoro-benzylamine (2.2 eq.) and triethylamine (2 eq.) were added. The mixture was stirred at 65° C. for 16 h. After cooling to room temperature the mixture was partitioned between aq. ammonium chloride and dichloromethane. The aq. phase was again extracted with dichloromethane. The combined organic phases were then extracted with 0.1 M NaOH. The aq. phase was then acidified to pH 5 ca. with 1 M aq. HCl and extracted with dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated to dryness. The crude product so obtained was used in the subsequent step without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was removed under high vacuum
  3. dissolutionThe residue was dissolved in methanol
  4. stirringThe mixture was stirred at 65° C. for 16 h
  5. temperatureAfter cooling to room temperature the mixture
  6. customwas partitioned between aq. ammonium chloride and dichloromethane
  7. extractionThe aq. phase was again extracted with dichloromethane
  8. extractionThe combined organic phases were then extracted with 0.1 M NaOH
  9. extractionextracted with dichloromethane
  10. dry with materialThe organic phase was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fc9aba8f4c8546c08b9c8637c467b492
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07968553B2

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