Water → HCID 22132568, compound

HRID 1856760Notes

Reaction equation

HRID 1856760 reaction equation
[Cl:1][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][NH:16][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.[H-].[Na+].[CH3:36]I.O>CN(C)C=O>[Cl:1][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]([CH3:36])[C:17]([N:19]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]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

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 22132609HCID 22132609, compound

Product 1

HCID 22132568HCID 22132568, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-6-{3-[3-cyclohexyl-3-(2-acetyloxybutyl)ureido]propoxy}quinoline (5.6 g) in dimethylformamide (80 ml) is added sodium hydride (60% oily, 0.8 g), and the mixture is stirred at room temperature for one hour. To the reaction solution is added methyl iodide (1.1 ml), and the mixture is stirred for one hour. To the mixture is further added methyl iodide (2 ml), and the mixture is stirred at room temperature overnight. The reaction solution is poured into water, and extracted with ethyl acetate. The ethyl acetate layer is separated, washed with water, and dried over anhydrous magnesium sulfate. The resultant is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1) to give 2-chloro-6-{3-[1-methyl-3-cyclohexyl-3-(2-acetyloxybutyl)ureido]propoxy}quinoline (5.5 g) as a colorless oil.

Workup

  1. stirringthe mixture is stirred for one hour
  2. stirringthe mixture is stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer is separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe resultant is concentrated under reduced pressure
  8. customto remove the solvent
  9. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-cf19b87d88094e43a273d96d23e71ee4
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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