Water → 2-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

HRID 916539Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-25858ee9eec24a5fb3e45f1f18bc355c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271130B2

Reaction notes

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