Ethanolamine → 2-{2-[6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yloxy]-ethylamino}-ethanol

HRID 229094Notes

Reaction equation

HRID 229094 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[C:17]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=4)=[N:18][C:19]([CH3:23])=[C:20]([CH3:22])[CH:21]=3)=[CH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].[NH2:39][CH2:40][CH2:41][OH:42]>CN(C)C=O>[CH3:32][O:31][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:3][CH2:2][NH:39][CH2:40][CH2:41][OH:42])[N:12]=[CH:11][CH:10]=[C:9]2[O:15][C:16]1[C:17]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=2)=[N:18][C:19]([CH3:23])=[C:20]([CH3:22])[CH:21]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 577563443-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,5'-trimethyl-[2,2']bipyridine2×

Product 1

HCID 577565332-{2-[6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yloxy]-ethylamino}-ethanolYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-5,6,5′-trimethyl-[2,2′]bipyridine (compound 466) (33 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (101 mg) and 2-aminoethanol (0.13 ml) were added to the solution, and the mixture was stirred at 70° C. overnight. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (25 mg, yield 71%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-5e88946be35049188bbce34fd71f9eaf
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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