Water → HCID 14998348, compound

HRID 1109716Notes

Reaction equation

HRID 1109716 reaction equation
[F:1][C:2]1[C:15]([N:16]2[C:20](=[O:21])[C:19](=[C:22]([CH3:24])[CH3:23])[NH:18][C:17]2=[O:25])=[CH:14][C:5]2[N:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH3:26][N:18]1[C:19](=[C:22]([CH3:23])[CH3:24])[C:20](=[O:21])[N:16]([C:15]2[C:2]([F:1])=[CH:3][C:4]3[O:9][CH2:8][C:7](=[O:10])[N:6]([CH2:11][C:12]#[CH:13])[C:5]=3[CH:14]=2)[C:17]1=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14998347HCID 14998347, compound

Product 1

HCID 14998348HCID 14998348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-[7-fluoro-4-propargyl-2H-1,4-bezoxazin-3(4H)-on-6-yl]-5-isopropylidenehydantoin (1.2 g), potassium carbonate (3.0 g) and iodomethane (3.0 g) were dissolved in N,N-dimethylformamide (30 ml), followed by heating at 70° C. for 6 hours. The reaction mixture was allowed to cool, combined with water and extracted with ethyl acetate. The organic layer was purified by silica gel column chromatography using a mixture of toluene and ethyl acetate as the eluent to give Compound No. 32 (1.1 g).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was purified by silica gel column chromatography
  4. additiona mixture of toluene and ethyl acetate as the eluent
  5. customto give Compound No

Sources & evidence

ORD record
ord-854ec200e7144128be5f19ed37b4ac36
Source dataset
uspto-grants-1994_06
Patent number
US05322835

Reaction notes

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