1-Iodohexane → 6,8-Difluoro-2-[4-(N,N-dimethylamino)-3-fluorophenyl]-5-hexylamino-4H-1-benzopyran-4-one

HRID 1736130Notes

Reaction equation

HRID 1736130 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([F:30])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[C:13]([F:20])[CH:12]=3)=[CH:8][C:7](=[O:21])[C:6]=2[C:22]=1[NH:23][C:24](=O)[C:25](C)([CH3:27])C.[H-].[Na+].I[CH2:34][CH2:35][CH2:36]CCC.[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([F:30])[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[C:13]([F:20])[CH:12]=3)=[CH:8][C:7](=[O:21])[C:6]=2[C:22]=1[NH:23][CH2:24][CH2:25][CH2:27][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19434956HCID 19434956, compound

Product 1

HCID 194349746,8-Difluoro-2-[4-(N,N-dimethylamino)-3-fluorophenyl]-5-hexylamino-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (1.50 mmol) of Compound 38 obtained in Example 38 was dissolved in 5 ml of dimethylformamide under argon atmosphere, 120 mg of sodium hydride (60% oil disperison) and 0.441 ml of 1-iodohexane were added under ice-cooling and the mixture was stirred at room temperature for 3 hours. An aqueous saturated solution of ammonium chloride was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) and recrystallized from n-hexane/ethyl acetate to give Compound 58 which was converted into hydrochloride according to the same manner as that in Example 16 to give 494 mg (79%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed 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. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)
  7. customrecrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-7720cb9c8aa948659ee8021d02fb8913
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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