Water → 2-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide
Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([CH3:27])[C:24]#[C:25][CH3:26])=[O:21].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)[O:11][CH:19]([CH2:29][O:30][CH3:31])[C:20]([NH:22][C:23]([CH3:28])([C:24]#[C:25][CH3:26])[CH3:27])=[O:21])#[N:2]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
3-Cyano-5-methoxyphenol (prepared as described in J. Med. Chem. (1993), 36, No 16, 2367; 0.119 g) in dry N,N-dimethylformamide (3 ml) containing anhydrous potassium carbonate (0.168 g) and 2-bromo-N-(4-methylpent-2-yn-4-yl) 3-methoxypropionamide (0.210 g) were stirred and heated to 80° C. for 5 hours. The mixture was cooled to ambient temperature, stored for 2 days then poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; hexane/ethyl acetate 3:2 by volume) to give the required product (0.110 g) as a colourless gum.
Aufarbeitung
- temperatureThe mixture was cooled to ambient temperature
- extractionextracted with ethyl acetate
- washwashed with water
- dry with materialdried over magnesium sulphate
- customthen evaporated under reduced pressure
- customto give a brown gum
Quellen und Nachweise
- ORD-Eintrag
- ord-25858ee9eec24a5fb3e45f1f18bc355c
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07271130B2
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