Water → HCID 86591478, compound

HRID 388029Notes

Reaction equation

HRID 388029 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([C:19]#[N:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:22][C:23]([NH:25][CH3:26])=[O:24].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].O.[C:39]([O:42][CH2:43][CH3:44])(=O)C>>[C:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH2:44][C@H:43]1[CH2:39][O:42]1)[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:6]1[CH:5]=[CH:4][C:3]([NH:22][C:23]([NH:25][CH3:26])=[O:24])=[C:2]([Cl:1])[CH:7]=1)#[N:20]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135829408N-(2-chloro-4-(6-cyano-7-hydroxyquinolin-4-yloxy)phenyl)-N'-methylurea

Product 1

HCID 86591478HCID 86591478, compound

Conditions

Temperature
50 °C

Procedure

N-[2-Chloro-4-(6-cyano-7-hydroxyquinolin-4-yloxy)phenyl]-N′-methylurea (600 mg) was added to dimethylformamide (4 ml), and then p-toluenesulfonic acid (2R)-glycidyl ester (484 mg) and potassium carbonate (450 mg) were added thereto and the mixture was heated at 50° C. for 4 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized with ethyl acetate to obtain the title compound (650 mg) as light yellow crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-894867134a644d45991e850a8936fc02
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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