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

HRID 884500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884500
[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-a3563e87f4104ce3a73fe7c18b0cd0b6
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242126B2

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