Water → (4-Tert-butylphenyl)-{4-[6-methoxy-7-(1-propylpiperidin-4-ylmethoxy)quinolin-4-yloxy]phenyl}amine

HRID 1727862Notes

Reaction equation

HRID 1727862 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][CH:33]5[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:46][CH2:47][CH3:48].O>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][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][CH:33]5[CH2:38][CH2:37][N:36]([CH2:46][CH2:47][CH3:48])[CH2:35][CH2:34]5)=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 69055371(4-Tert-butylphenyl)-{4-[6-methoxy-7-(4-piperidinylmethoxy)-4-quinolyloxy]phenyl}amine

Product 1

HCID 57567608(4-Tert-butylphenyl)-{4-[6-methoxy-7-(1-propylpiperidin-4-ylmethoxy)quinolin-4-yloxy]phenyl}amineYield 7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Tert-butylphenyl)-{4-[6-methoxy-7-(4-piperidinylmethoxy)-4-quinolyloxy]phenyl}amine (150 mg) was dissolved in N,N-dimethylformamide (3 ml) to prepare a solution. Potassium carbonate (300 mg) and 1-bromopropane (0.15 ml) were then added to the solution, and the mixture was stirred at room temperature for 4 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. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by thin-layer chromatography on silica gel using chloroform/acetone for development to give the title compound (12 mg, yield 7%).

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-66769e3d155e4d3daace0889219cb3b3
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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