Water → 2-(5-chloro-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)-3-methoxypropionamide

HRID 1374917Notes

Reaction equation

HRID 1374917 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([CH2:26][O:27][CH3:28])[C:17]([NH:19][C:20]([CH3:25])([CH3:24])[C:21]#[C:22][CH3:23])=[O:18].O>CN(C)C=O.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:16]([CH2:26][O:27][CH3:28])[C:17]([NH:19][C:20]([CH3:25])([CH3:24])[C:21]#[C:22][CH3:23])=[O:18])[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5823053-Hydroxy-5-chloropyridineHCID 210784052-bromo-3-methoxy-N-(4-methylpent-2-yn-4-yl)propionamide

Product 1

HCID 210783902-(5-chloro-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)-3-methoxypropionamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chloro-5-hydroxypyridine (0.074 g), anhydrous potassium carbonate (0.087 g) and 2-bromo-N-(4-methylpent-2-yn-4-yl)-3-methoxypropionamide (0.150 g) in dry N,N-dimethylformamide (3 ml) were stirred at 80° C. for 5 hours. The mixture was allowed to cool to ambient temperature and stored for 2 days. The mixture was poured into water, extracted with ethyl acetate and the organic phases were combined, washed with water, dried over magnesium sulphate and evaporated under reduced pressure to a gum. The gum was fractionated by chromatography (silica; ethyl acetate:hexane, 2:3 by volume) to give a colourless gum that was dissolved in diethyl ether and extracted with aqueous hydrochloric acid (3M). The aqueous acidic fraction was collected and treated with potassium carbonate until basic then extracted with diethyl ether. The ether extracts were combined, dried over magnesium sulphate and evaporated under reduced pressure to give the required product, 0.094 g, as a colourless gum.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure to a gum
  5. customto give a colourless gum that
  6. extractionextracted with aqueous hydrochloric acid (3M)
  7. customThe aqueous acidic fraction was collected
  8. additiontreated with potassium carbonate until basic
  9. extractionthen extracted with diethyl ether
  10. dry with materialdried over magnesium sulphate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-04ff5acff9934701946d8942ad6da789
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

Loading…