Acetamide → N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide

HRID 546582Notizen

Reaktionsgleichung

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22](Cl)[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:34]([NH2:37])(=[O:36])[CH3:35]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:37][C:34](=[O:36])[CH3:35])[CH:21]=3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 400 mg of 3-(4-tert-butylphenyl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage a) below in 12 mL of dioxane are successively added, under argon, 23.3 mg of palladium diacetate, 72 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)[Xantphos], 1.18 g of caesium carbonate and 153 mg of acetamide. After heating for one hour at a temperature in the region of 90° C. and chromatography on a column of silica, eluting with a mixture of diethyl ether/ethyl acetate (gradient up to 100% of ethyl acetate), 370 mg of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide are obtained in the form of white crystals, the characteristics of which are as follows:

Aufarbeitung

washeluting with a mixture of diethyl ether/ethyl acetate (gradient up to 100% of ethyl acetate), 370 mg of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide
customare obtained in the form of white crystals

Quellen und Nachweise

ORD-Eintrag: ord-04efd9ee0b3b477fa4931493facce397
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07935819B2

Notizen zur Reaktion

Wird geladen…