Sodium Iodide → HCID 19434793, compound

HRID 1736120Notes

Reaction equation

HRID 1736120 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH3:6].[I-].[Na+].[C:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][C:21]3[C:29]([F:30])=[CH:28][C:27]([F:31])=[C:26]([NH2:32])[C:22]=3[C:23](=[O:25])[CH:24]=2)=[CH:15][C:14]=1[F:33])(=[O:11])[CH3:10].[H-].[Na+]>CN(C)C=O.O>[C:9]([N:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][C:21]3[C:29]([F:30])=[CH:28][C:27]([F:31])=[C:26]([NH2:32])[C:22]=3[C:23](=[O:25])[CH:24]=2)=[CH:15][C:14]=1[F:33])[CH2:2][CH2:3][CH2:4][O:5][CH3:6])(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydride2×HCID 1189271-Chloro-3-methoxypropane2×HCID 194349072-(4-Acetylamino-3-fluorophenyl)-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

Product 1

HCID 19434793HCID 19434793, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

949 mg of 1-chloro-3-methoxypropane and 1.30 g of sodium iodide were dissolved in 20 ml of dimethylformamide under argon atmosphere and the mixture was stirred at 90° C. for 2 hours. The reaction solution was cooled on ice and 1.51 g (4.35mmol) of Compound 27 obtained in Example 27 and 89 mg of sodium hydride (60% oil dispersion) were added thereto. The mixture was stirred at room temperature for 1 hour, 943 mg of 1-chloro-3-methoxypropane and 191 mg of sodium hydride (60% oil dispersion) were added, the temperature was raised to 60° C. and the mixture was stirred for 2 days. 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. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give 1.18 g (65%) of 2-[4-[N-acetyl-N-(3-methoxypropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. temperaturethe temperature was raised to 60° C.
  4. stirringthe mixture was stirred for 2 days
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-02814048993f4b2e98b949c46f153d52
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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