Potassium Carbonate → HCID 57785955, compound

HRID 1399017Notes

Reaction equation

HRID 1399017 reaction equation
C([O:4][CH2:5][CH:6]1[CH2:13][N:12]2[C:8](=[N:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:11]=32)[N:7]1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[N:7]1[C:8]2=[N:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:11]=3[N:12]2[CH2:13][CH:6]1[CH2:5][OH:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57786041HCID 57786041, compound

Product 1

HCID 57785955HCID 57785955, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [1-(2,4-dichlorophenyl)-5-(diethylamino)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-2-yl]methyl acetate (30.5 mg, 0.0682 mmol) in methanol (0.7 mL) was added potassium carbonate (9.4 mg, 0.0682 mmol) at room temperature. After 1 hr, the mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (24.1 mg, 0.0593 mmol, 87%). Analytically pure material was obtained by recrystallization from ethyl acetate/n-hexane.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-70% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-f96e40b78ea949c18206274b61be7744
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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