Ethyl 1-propenyl ether → 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595668

반응식

HRID 595668 반응식
[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10](Cl)=[N:11][OH:12])=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[C:6]=2[CH:18]=1.[CH2:25]([O:27][CH:28]=[CH:29][CH3:30])[CH3:26].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:29]([CH3:30])[CH:28]([O:27][CH2:25][CH3:26])[O:12][N:11]=3)=[C:7]([C:14]([NH:15][CH3:16])=[O:17])[C:6]=2[CH:18]=1

참가 물질

5

반응물 3

HCID 13570Ethyl 1-propenyl etherHCID 516892Sodium BicarbonateHCID 903324475-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride

생성물 1

HCID 903324215-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide수율 83.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride (400 mg, 0.91 mmol), 1-ethoxyprop-1-ene (392 mg, 4.56 mmol) and NaHCO3 (153 mg, 1.82 mmol) in DMF (10 mL) was stirred at room temperature for 16 h. It was concentrated, diluted with water, extracted with EtOAc, the organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (PE:EA=2:1) to get product 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (370 mg, yield: 83%). MS (M+H)+: 488/490.

후처리

  1. concentrationIt was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washthe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (PE:EA=2:1)

출처 및 근거

ORD 기록
ord-ade4085fa6194ffaae10b313b720147a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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