Water → HCID 19434902, 화합물

HRID 1736121노트

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HRID 1736121 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:29][CH2:30][CH2:31][Cl:32].O>CN(C)C=O>[C:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:21]([F:22])=[CH:20][C:19]([F:23])=[C:18]([NH2:24])[C:14]=3[C:15](=[O:17])[CH:16]=2)=[CH:7][C:6]=1[F:25])[CH2:29][CH2:30][CH2:31][Cl:32])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 194349072-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

생성물 1

HCID 19434902HCID 19434902, 화합물수율 35%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1.02 g (2.92 mmol) of Compound 27 obtained in Example 27 was dissolved in 25 ml of dimethylformamide under argon atmosphere, 129 mg of sodium hydride (60% oil dispersion) and 2.9 ml of 1-bromo-3-chloropropane were added under ice-cooling and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. Recrystallization from ethyl acetate/acetonitrile afforded 434 mg (35%) of 2-[4-[N-acetyl-N-(3-chloropropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customRecrystallization from ethyl acetate/acetonitrile

출처 및 근거

ORD 기록
ord-fa768f877a1044eabb8971d953e1bd96
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539112

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