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

HRID 916539노트

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HRID 916539 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 210784052-bromo-3-methoxy-N-(4-methylpent-2-yn-4-yl)propionamideHCID 229962023-Hydroxy-5-methoxybenzonitrile

생성물 1

HCID 691147962-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

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온도
80 °C

실험 절차

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.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure
  6. customto give a brown gum

출처 및 근거

ORD 기록
ord-25858ee9eec24a5fb3e45f1f18bc355c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271130B2

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