Potassium Carbonate → N-Isopropyl-2-[2-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-benzofuran-7-yloxy]-acetamide

HRID 132601

Reaction equation

HRID 132601 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([C:11]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[CH2:26][C:27]([NH:29][CH:30]([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:30]([NH:29][C:27](=[O:28])[CH2:26][O:1][C:2]1[C:10]2[O:9][C:8]([C:11]([C:13]3[C:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:15][O:16][C:17]=3[CH3:18])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 761712-chloro-N-(1-methylethyl)acetamideHCID 16665213(7-Hydroxy-2-benzofuranyl)(5-methyl-3-phenyl-4-isoxazolyl)methanone

Product 1

HCID 16061484N-Isopropyl-2-[2-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-benzofuran-7-yloxy]-acetamideYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (7-hydroxy-2-benzofuranyl)(5-methyl-3-phenyl-4-isoxazolyl)methanone (example 4) (100 mg, 0.31 mmol) in DMF (5 mL) was added N-(chloroacetyl)isopropylamine (47 mg, 0.34 mmol) and potassium carbonate (173 mg, 1.25 mmol) and the reaction mixture was stirred at room temperature for 4 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1) afforded the title compound (37 mg, 28%) as a white solid. MS m/e: 419.3 [M+H]+.

Workup

  1. additionThe mixture was then poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 1:1)

Sources & evidence

ORD record
ord-950d29591c214990904ac7f450664db7
Source dataset
uspto-grants-2008_06
Patent number
US07388025B2

Linked notes

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