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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
Notes
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Reaction equation

HRID 1736193 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-6af839ad06ab4b158c361e706f20520d
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05539112

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes