Acetic Anhydride → HCID 22132609, compound

HRID 1856759Notes

Reaction equation

HRID 1856759 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:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:20][CH:21]([OH:24])[CH2:22][CH3:23])=[O:18])[CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:38](OC(=O)C)(=[O:40])[CH3:39]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[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:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[CH2:20][CH:21]([O:24][C:38](=[O:40])[CH3:39])[CH2:22][CH3:23])=[O:18])[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22132564HCID 22132564, compound

Product 1

HCID 22132609HCID 22132609, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-6-{3-[3-cyclohexyl-3-(2-hydroxybutyl)ureido]-propoxy}quinoline (6.3 g), 4-dimethylaminopyridine (0.1 g) and triethylamine (2.3 g) in methylene chloride (80 ml) is added dropwise with stirring acetic anhydride (1.8 g) at room temperature. The methylene chloride layer is washed successively with diluted hydrochloric acid, water and a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The resultant is concentrated under reduced pressure to remove the solvent to give 2-chloro-6-[3-[3-cyclohexyl-3-(2-acetyloxybutyl)ureido]-propoxy]quinoline (6.7 g) as a colorless oil.

Workup

  1. washThe methylene chloride layer is washed successively with diluted hydrochloric acid, water
  2. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate
  3. concentrationThe resultant is concentrated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-fdfaa1449d894cd19a621a1b1ccbb5c6
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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