1-Iodohexane → 2-[4-[N-acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-one

HRID 1736112Notes

Reaction equation

HRID 1736112 reaction equation
[C:1]([N:4]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]3[C:35]([F:36])=[CH:34][C:33]([F:37])=[C:32]([NH2:38])[C:28]=3[C:29](=[O:31])[CH:30]=2)=[CH:21][C:20]=1[F:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])(=[O:3])[CH3:2].I[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[C:1]([N:4]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][C:27]3[C:35]([F:36])=[CH:34][C:33]([F:37])=[C:32]([NH:38][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:28]=3[C:29](=[O:31])[CH:30]=2)=[CH:21][C:20]=1[F:39])[CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 153469942-[4-[N-Acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Product 1

HCID 194348532-[4-[N-acetyl-N-(3-phthalimidopropyl)amino]-3-fluorophenyl]-6,8-difluoro-5-hexylamino-4H-1-benzopyran-4-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

450 mg of Compound 28 was dissolved in 15 ml of dimethylformamide, 0.62 ml of 1-iodohexane and 34 mg of sodium hydride (60% oil dispersion) were added under ice-cooling and the mixture was stirred at room temperature for 2 hours. An aqueous solution of ammonium chloride was added, the reaction solution was concentrated under reduced pressure and the residue was extracted once with chloroform. The chloroform layer was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:1-1:3) to give 184 mg (35%) of Compound 31.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. extractionthe residue was extracted once with chloroform
  4. washThe chloroform layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11a3c305d37d4c018bdc7b9eb71573db
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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