Water → (4-Tert-butylphenyl)-{4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yloxy]phenyl}amine

HRID 1727855Notes

Reaction equation

HRID 1727855 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][CH2:34]Cl)=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(B(O)O)=CC=1)(C)(C)C.O.[C:50]([O:53][CH2:54][CH3:55])(=O)[CH3:51].C[N:57](C)C=O>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][CH2:34][N:57]5[CH2:55][CH2:54][O:53][CH2:50][CH2:51]5)=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 27343204-tert-Butylphenylboronic acid2×HCID 57567448(4-Tert-butylphenyl)-{4-[7-(3-chloropropoxy)-6-methoxy-4-quinolyloxy]phenyl}amine2×

Product 1

HCID 57567419(4-Tert-butylphenyl)-{4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yloxy]phenyl}amineYield 27%

Conditions

Temperature
70 °C

Procedure

(4-Tert-butylphenyl)-{4-[7-(3-chloropropoxy)-6-methoxy-4-quinolyloxy]phenyl}amine (40 mg) (starting compound A) was dissolved in N,N-dimethylformamide (1 ml) to prepare a solution. Morpholine (30 μl) (starting compound B) was then added to the solution, and the mixture was stirred at 70° C. for 2 days. 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. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by thin-layer chromatography on silica gel using chloroform/methanol for development to give the title compound (12 mg, yield 27%).

Workup

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

Sources & evidence

ORD record
ord-7879dd11722e4a7aa9dda4ff05e588c4
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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