Imidazole → HCID 22132564, compound

HRID 1856758Notes

Reaction equation

HRID 1856758 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.N1C=CN=C1.[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])[CH:25]=2)[N:20]=1.[OH:34][CH:35]([CH2:44][CH3:45])[CH2:36][NH:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH2:30][CH2:31][CH2:32][NH:33][C:6]([N:37]([CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:36][CH:35]([OH:34])[CH2:44][CH3:45])=[O:7])[CH:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 419885HCID 419885, compoundHCID 22132608HCID 22132608, compound

Product 1

HCID 22132564HCID 22132564, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of N,N-carbonyldimidazole (2.1 g) and imidazole (1.9 g) in chloroform (100 ml) is added dropwise with stirring a solution of 2-chloro-6-(3-aminopropoxy)quinoline (3 g) in chloroform (40 ml) at -10° C. The mixture is stirred at room temperature overnight, and thereto is added dropwise a solution of N-(2-hydroxybutyl)-N-cyclohexylamine (2.9 g) in chloroform (10 ml). The mixture is stirred at room temperature for one hour, and refluxed for 2.5 hours. The mixture is allowed to cool, and the chloroform layer is washed successively with diluted hydrochloric acid, water and a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and evaporated to remove the solvent to give 2-chloro-6-{3-[3-cyclohexyl-3-(2-hydroxybutyl)ureido]propoxy}quinoline (6.8 g) as a colorless oil.

Workup

  1. stirringThe mixture is stirred at room temperature for one hour
  2. temperaturerefluxed for 2.5 hours
  3. temperatureto cool
  4. washthe chloroform layer is washed successively with diluted hydrochloric acid, water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent

Sources & evidence

ORD record
ord-f95d9e0d96a64e05887e50befe88f83b
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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