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

HRID 132601

반응식

HRID 132601 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-950d29591c214990904ac7f450664db7
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388025B2

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