Sodium percarbonate → HCID 59987479, compound

HRID 658505Notes

Reaction equation

HRID 658505 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[C:14]([F:16])[C:13]([NH:17][C:18]([NH:20][C:21]3[CH:34]=[CH:33][C:24]4[O:25][C:26]([F:32])([F:31])[O:27][C:28]([F:30])([F:29])[C:23]=4[CH:22]=3)=[O:19])=[C:12]([F:35])[CH:11]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C([O-])([O-])=[O:37].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>CC(C)=O.O>[F:35][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([F:16])[C:13]=1[NH:17][C:18]([NH:20][C:21]1[CH:34]=[CH:33][C:24]2[O:25][C:26]([F:31])([F:32])[O:27][C:28]([F:29])([F:30])[C:23]=2[CH:22]=1)=[O:19])[O:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:37])[CH:8]=1

Participants

5

Reactant 2

HCID 159762Sodium percarbonateHCID 10006002HCID 10006002, compound

Product 1

HCID 59987479HCID 59987479, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of N-{4-[(2-cyanopyridin-4-yl)oxy]-2,6-difluorophenyl}-N′-(2,2,4,4-tetra-fluoro-4H-1,3-benzodioxin-6-yl)urea (100 mg, 0.20 mmol) in acetone (2 ml) and water (1 ml) was treated with sodium percarbonate (contain 25% H2O2, 320 mg, 2.0 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate (20 ml) and water (10 ml). The organic layer was washed with water (10 ml) and brine (5 ml), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was crystallized from methanol providing 42 mg (41%) of title compound as a white solid. 1H-NMR (DMSO-d6) δ 9.48 (s, 1H), 8.56 (d, J=6.0 Hz, 1H), 8.31 (s, 1H), 8.15 (s, 1H), 8.07 (d, J=2.2 Hz, 1H), 7.74 (s, 1H), 7.68 (dd, J=9.2, 2.7 Hz, 1H), 7.46 (d, J=2.3 Hz, 1H), 7.41 (d, J=9.3 Hz, 1H), 7.25 (m, 2H); MS GC-MS M+=515.0, RT=3.63 min.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (20 ml) and water (10 ml)
  2. washThe organic layer was washed with water (10 ml) and brine (5 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from methanol providing 42 mg (41%) of title compound as a white solid

Sources & evidence

ORD record
ord-d5c709c43e834310ae7555f71d552f8b
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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