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Butyl iodide → 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736193
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HRID 1736193 반응식
[C:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH2:30])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:31])[CH2:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])(=[O:3])[CH3:2].I[CH2:33][CH2:34][CH2:35][CH3:36].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([N:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=3[C:21](=[O:23])[CH:22]=2)=[CH:13][C:12]=1[F:31])[CH2:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 194349202-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

생성물 1

HCID 194349352-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one수율 63.4%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

1.01 g (2.35 mmol) of 2-[4-[N-acetyl-N-(3-azidopropyl) amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one obtained in Example 79 was dissolved in 30 mL of dimethylformamide under argon atmosphere, 1.34 mL (11.8 mmol) of 1-iodobutane and 190 mg (4.75 mmol) of sodium hydride (60% oil dispersion) were added and the mixture was stirred at room temperature for 45 minutes. An aqueous solution of ammonium chloride 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. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 726 mg of 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-butylamino-6,8-difluoro-4H-1-benzopyran-4-one (yield: 63%).

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-6af839ad06ab4b158c361e706f20520d
출처 데이터셋
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05539112

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