Dimethylformamide → (4-Tert-butylphenyl)-{4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yloxy]phenyl}amine

HRID 1727860Notes

Reaction equation

HRID 1727860 reaction equation
CN(C)C=O.[C:6]([C:10]1[CH:36]=[CH:35][C:13]([NH:14][C:15]2[CH:34]=[CH:33][C:18]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([OH:32])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>C(OCC)(=O)C.O>[C:6]([C:10]1[CH:36]=[CH:35][C:13]([NH:14][C:15]2[CH:34]=[CH:33][C:18]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH2:45][CH2:46][N:47]5[CH2:52][CH2:51][O:50][CH2:49][CH2:48]5)=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 1357802514-[4-(4-Tert-butylphenylamino)phenoxy]-6-methoxyquinolin-7-ol2×

Product 1

HCID 44382806(4-Tert-butylphenyl)-{4-[6-methoxy-7-(2-morpholin-4-ylethoxy)quinolin-4-yloxy]phenyl}amineYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
77.5 °C

Procedure

N,N-Dimethylformamide (2 ml) was added to 4-{4-[4-(tert-butyl)anilino]phenoxy}-6-methoxy-7-quinolinol (compound 21) (100 mg), potassium carbonate (167 mg), and 4-(2-chloroethyl)morpholine hydrochloride (70 mg), and the mixture was stirred at 75 to 80° C. for 6 hr. Water and ethyl acetate were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate, and the solvent was then removed by evaporation under the reduced pressure. The crude thus obtained was purified by thin-layer chromatography on silica gel using chloroform/methanol for development to give the title compound (102 mg, yield 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialwas dried over sodium sulfate
  4. customthe solvent was then removed by evaporation under the reduced pressure
  5. customThe crude thus obtained
  6. customwas purified by thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-ec95c95eda35440a8372e7a7e138ae75
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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