Sodium hydride → HCID 131724510, compound

HRID 1835044Notes

Reaction equation

HRID 1835044 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:29])=[CH:14][C:15]3[O:20][CH2:19][C:18](=[O:21])[NH:17][C:16]=3[C:22]=2[NH:23][C:24](=[O:28])[CH:25](Cl)[CH3:26])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:12]2[C:22]3[NH:23][C:24](=[O:28])[CH:25]([CH3:26])[N:17]4[C:18](=[O:21])[CH2:19][O:20][C:15]([C:16]=34)=[CH:14][C:13]=2[F:29])=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23502528HCID 23502528, compound

Product 1

HCID 131724510HCID 131724510, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-3-[7-fluoro-5-(2-chloropropionylamino)-2H-1,4-benzoxazine-3(4H)-on-6yl]-1-methyl-5-difluoromethoxy-1H-pyrazole (300 mg, 0.66 mmol) was dissolved in anhydrous dimethylformamide (10 ml) and solution stirred under ice-cooling. Sodium hydride (20 mg, 95%, 0.79 mmol) was added slowly in portions and solution stirred at room temperature for 2 hr. Solution was then added to ice-water and product extracted with ethyl acetate. Evaporation of the solvent afforded a residue which was purified by flash chromatography on silica gel in hexane-ethyl acetate (1:1) to furnish the title compound (209.2 mg, 0.50 mmol).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 2 hr
  3. extractionextracted with ethyl acetate
  4. customEvaporation of the solvent
  5. customafforded a residue which
  6. customwas purified by flash chromatography on silica gel in hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-4b24f6fc3fb340b48649ef640a0125fa
Source dataset
uspto-grants-2004_08
Patent number
US06770596B1

Reaction notes

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