Piperidine → 7-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-one

HRID 1619345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619345
C1C2C(COC([N:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[C:23]3[NH:32][C:31](=[O:33])[C:30]4[C:25](=[CH:26][C:27]([Br:34])=[CH:28][CH:29]=4)[N:24]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CC#N.O>[Br:34][C:27]1[CH:26]=[C:25]2[C:30]([C:31](=[O:33])[NH:32][C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][NH:18]3)=[N:24]2)=[CH:29][CH:28]=1

Komponenten

5

Edukt 2

HCID 8082PiperidineHCID 136038175(9H-fluoren-9-yl)methyl 2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate

Produkt 1

HCID 1360381767-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-oneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (9H-fluoren-9-yl)methyl-2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate (305 mg, 1.04 mmol) and piperidine (2 mL) in CH3CN was stirred at room temperature for 2 h. The mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give 162 mg of the desired product. MS (ESI): 294, 296 (MH+)

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e4ebb1c2626e4c6994098f4a2646c673
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772301B2

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