Water → HCID 91406855, compound

HRID 1835048Notes

Reaction equation

HRID 1835048 reaction equation
Br[C:2]([CH3:30])([CH3:29])[C:3]([NH:5][C:6]1[C:11]2[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=2[CH:9]=[C:8]([F:17])[C:7]=1[C:18]1[C:22]([Cl:23])=[C:21]([C:24]([F:27])([F:26])[F:25])[N:20]([CH3:28])[N:19]=1)=[O:4].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:23][C:22]1[C:18]([C:7]2[C:6]3[NH:5][C:3](=[O:4])[C:2]([CH3:30])([CH3:29])[N:12]4[C:13](=[O:16])[CH2:14][O:15][C:10]([C:11]=34)=[CH:9][C:8]=2[F:17])=[N:19][N:20]([CH3:28])[C:21]=1[C:24]([F:27])([F:26])[F:25]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 23502532HCID 23502532, compound

Product 1

HCID 91406855HCID 91406855, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(2-Bromoisobutyrylamino)-6-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-7-fluoro-2H-1,4-benzoxazine-3(4H)-one (1.15 g, 2.24 mmol) was dissolved in anhydrous acetonitrile (50 ml) and potassium iodide (0.45 g, 2.70 mmol) and potassium carbonate (0.37 g, 2.70 mmol) were added. Solution was refluxed for 2 hr and water was added. Product was extracted with ethyl acetate and solvent evaporated. Column chromatography on silica gel using hexane-ethyl acetate (7:3) as eluent afforded the title compound (84.0 mg, 0.19 mmol).

Workup

  1. temperatureSolution was refluxed for 2 hr
  2. extractionProduct was extracted with ethyl acetate and solvent
  3. customevaporated

Sources & evidence

ORD record
ord-904d5ae8d5fb4af1a3477ea15b20ceb7
Source dataset
uspto-grants-2004_08
Patent number
US06770596B1

Reaction notes

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