Ethyl Acetate → 4-[3-(4-Chlorobenzyl)-6-(2,2-difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde

HRID 403563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403563
[F:1][CH:2]([F:25])[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:20][CH2:19][N:18]([CH:21]=[O:22])[CH2:17][CH2:16]1)[C:10](=[O:23])[NH:9][C:8]2=[O:24].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:9]2[C:8](=[O:24])[C:7]3[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:3][CH:2]([F:1])[F:25])[CH:6]=3)[N:11]([CH:15]3[CH2:20][CH2:19][N:18]([CH:21]=[O:22])[CH2:17][CH2:16]3)[C:10]2=[O:23])=[CH:29][CH:30]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 252533494-[6-(2,2-Difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde

Produkt 1

HCID 252535004-[3-(4-Chlorobenzyl)-6-(2,2-difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehydeAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.15 g of 4-[6-(2,2-difluoroethoxy)-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde obtained in stage 3.7, 0.096 g of 1-(bromomethyl)-4-chlorobenzene and 0.3 g of Cs2CO3 in 3 ml of DMF is stirred at AT for 1 h 00. AcOEt is added and washing is carried out with water and then with a saturated NaCl solution. The organic phase is dried over MgSO4, filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with AcOEt, to give 0.116 g of the expected product.

Aufarbeitung

  1. washwashing
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue is chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-60f9f1bcd7424e3fb6c80d377cf24f66
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748441B2

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