Potassium Carbonate → HCID 22936639, compound

HRID 1433373Notes

Reaction equation

HRID 1433373 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:23])=[CH:17][CH:16]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH2:41][CH2:42][CH2:43][Cl:44]>CN(C)C=O.[Cl-].[Na+].O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:40][CH2:41][CH2:42][CH2:43][Cl:44])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[O:23])=[CH:17][CH:16]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 135829399HCID 135829399, compound

Product 1

HCID 22936639HCID 22936639, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(4-(6-Cyano-7-hydroxy-4-quinolyl)oxyphenyl)-N′-(4-methoxyphenyl)urea (200 mg), potassium carbonate (65 mg) and 1-bromo-4-chlorobutane (81 μl) were suspended in dimethylformamide (3 ml), and the suspension was heated and stirred for 1 hour and 50 minutes. The reaction solution was poured into saturated brine and extracted with ethyl acetate. After drying the organic layer over magnesium sulfate, it was passed through NH silica (Fuji Silysia Chemical) and washed in ethyl acetate, and the filtrate was concentrated. The obtained solid was washed with ether and dried to obtain 110 mg of the title compound.

Workup

  1. temperaturethe suspension was heated
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter drying the organic layer over magnesium sulfate, it
  4. washwashed in ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. washThe obtained solid was washed with ether
  7. customdried

Sources & evidence

ORD record
ord-91da753e2da34c9c8694e93b075eac6b
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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