2-Methoxyethanol → HCID 22502472, compound

HRID 1007020Notes

Reaction equation

HRID 1007020 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4].[CH3:28][O:29][CH2:30][CH2:31][OH:32]>>[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:32][CH2:31][CH2:30][O:29][CH3:28])[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 22502633HCID 22502633, compound

Product 1

HCID 22502472HCID 22502472, compound

Procedure

60% oily sodium hydride (0.20 g) was added gradually to 2-methoxyethanol (50 ml), under ice-cooling. To the resulting solution was added 1-(4-ethylpiperazin-1-yl)-3-(2-chloropyridin-4-yl)isoquinoline (0.20 g) obtained in the previous Example, and the mixture was heated under reflux for 3 days. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purif ied water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol systemn), to give the title compound (0.12 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 days
  4. customThe reaction solution was evaporated
  5. additionto the resulting residue were added ethyl acetate and purif ied water
  6. washThe ethyl acetate layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol systemn)

Sources & evidence

ORD record
ord-74f0ed39373f4c46992225c87af75b7c
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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