Water → HCID 18536490, compound

HRID 412627Notes

Reaction equation

HRID 412627 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]3[N:27]([CH2:28][C:29](=[O:37])[NH:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[C:26]4[CH:38]=[CH:39][C:40]([C:42]#[N:43])=[CH:41][C:25]=4[N:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53].O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22][C:23]3[N:27]([CH2:28][C:29](=[O:37])[NH:30][CH:31]4[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]4)[C:26]4[CH:38]=[CH:39][C:40]([C:42]#[N:43])=[CH:41][C:25]=4[N:24]=3)[CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetate3×HCID 11430Potassium Carbonate2×HCID 18536489HCID 18536489, compound

Product 1

HCID 18536490HCID 18536490, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)-phenylaminomethyl]-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole (247 mg) in dimethylformamide (2.5 ml) were added potassium carbonate (175 mg) and ethyl bromoacetate (0.07 ml), and the mire was stirred at room temperature for 24 hours. Thereto were added potassium carbonate (175 mg) and ethyl bromoacetate (0.07 ml), and the mixture was stirred at room temperature for 24 hours. Further, ethyl bromoacetate (0.07 ml) was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (124 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. stirringthe mixture was stirred at room temperature for 24 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0031de820f8349e5b2e3704d07e5c100
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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