Acetic Acid → HCID 22132588, compound

HRID 1856768Notes

Reaction equation

HRID 1856768 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:34])[C:17]([N:19]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:20][CH:21]([O:24][C:25](=[O:27])[CH3:26])[CH2:22][CH3:23])=[O:18])[CH:8]=2)[N:3]=1.C(O)(=[O:37])C>>[CH3:34][N:16]([CH2:15][CH2:14][CH2:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:37])[CH:11]=[CH:10]2)[C:17]([N:19]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:20][CH:21]([O:24][C:25](=[O:27])[CH3:26])[CH2:22][CH3:23])=[O:18]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 22132568HCID 22132568, compound

Product 1

HCID 22132588HCID 22132588, compound

Procedure

To acetic acid (100 ml) is added 2-chloro-6-{3-[1-methyl-3-cyclohexyl-3-(2-acetyloxybutyl)ureido]propoxy}quinoline (5.5 g), and the mixture is refluxed for 4 hours. The mixture is concentrated under reduced pressure to remove the acetic acid, and the residue is dissolved in methylene chloride and washed with a saturated aqueous sodium hydrogen carbonate solution. The mixture is dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1), and recrystallized from methylene chloride-diethyl ether to give 6-{3-[1-methyl-3-cyclohexyl-3-(2-acetyloxybutyl)ureido]propoxy}carbostyril (2.7 g) as a white powder.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove the acetic acid
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialThe mixture is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1)
  10. customrecrystallized from methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-0d692d6f6bcb4faba0995c5bb28e5646
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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