Ethyl bromoacetate → Ethyl [6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetate

HRID 2383986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383986
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:27]#[N:28])[CH2:25][CH2:24][C:23]3[N:22]=[CH:21][NH:20][C:19](=[O:26])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:27]([C:16]1([C:6]2[C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:25][CH2:24][C:23]2[N:22]=[CH:21][N:20]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:19](=[O:26])[C:18]=2[CH2:17]1)#[N:28]

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1356204896-(4-Methoxydibenzo[b,d]furan-1-yl)-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

Produkt 1

HCID 24804607Ethyl [6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in example 13 (170 mg, 0.46 mmol) in 5 ml of dry DMF was added ethyl bromoacetate (84.5 mg, 0.5 mmol) and cesium carbonate (195.6 mg, 0.6 mmol) at room temperature for 1 hr. Once the reaction has completed, the reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, followed by brine, and concentrated under vacuum. The crude product was purified by column chromatography to get 175 mg (83.2% yields) of the product. MP-106.2-125.1° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by column chromatography
  5. customto get
  6. custom175 mg (83.2% yields) of the product

Quellen und Nachweise

ORD-Eintrag
ord-d15a430eee7b45aab6022df6551f4cce
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263648B2

Notizen zur Reaktion

Wird geladen…