Potassium Carbonate → HCID 22936639, compound

HRID 387723Notes

Reaction equation

HRID 387723 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>[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

5

Reactant 3

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

Product 1

HCID 22936639HCID 22936639, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 saline and extracted with ethyl acetate. After drying the organic layer over magnesium sulfate, it was passed through NH silica (Fuji Silicia 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. additionThe reaction solution was poured into saturated saline
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying the organic layer over magnesium sulfate, it
  5. washwashed in ethyl acetate
  6. concentrationthe filtrate was concentrated
  7. washThe obtained solid was washed with ether
  8. customdried

Sources & evidence

ORD record
ord-ff6f8f1a24f94495bf7cebbcd457bb23
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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