Potassium Carbonate → 1-[2-Oxo-1-phenyl-2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]-1,3-dihydrobenzimidazol-2-one

HRID 1643952Notes

Reaction equation

HRID 1643952 reaction equation
CCN=C=NCCCN(C)C.Cl.[O:13]=[C:14]1[N:18]([CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([OH:22])=O)[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[NH:15]1.C1C=CC2N(O)N=NC=2C=1.[N:43]1[CH:48]=[CH:47][C:46]([N:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:45][CH:44]=1.C(N(C(C)C)C(C)C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:22]=[C:20]([N:52]1[CH2:53][CH2:54][N:49]([C:46]2[CH:47]=[CH:48][N:43]=[CH:44][CH:45]=2)[CH2:50][CH2:51]1)[CH:19]([N:18]1[C:17]2[CH:29]=[CH:30][CH:31]=[CH:32][C:16]=2[NH:15][C:14]1=[O:13])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 705171-(4-Pyridyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66754578(2-Oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid

Product 1

HCID 249011691-[2-Oxo-1-phenyl-2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]-1,3-dihydrobenzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

179 mg (0.94 mmol) of EDCl were added to a solution of 193 mg (0.72 mmol) of (2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid (VIIId), 106 mg (0.79 mmol) of HOBt, 117 mg (0.72 mmol) of 1-pyridin-4-ylpiperazine and 0.49 ml (2.87 mmol) of ethyldiisopropylamine in dichloromethane (8 ml) while stirring in an ice-water bath. The reaction solution was slowly warmed and stirred at room temperature for 16 h. Half-saturated aqueous potassium carbonate solution was added, and the organic phase was separated off. The aqueous phase was extracted with ethyl acetate (4×50 ml) and the combined organic phases were washed with sat. NaHCO3 solution, dried over magnesium sulfate and concentrated under reduced pressure. The reaction product was used without further purification for the next reaction step. Yield: 292 mg (98%) of yellow solid

Workup

  1. temperatureThe reaction solution was slowly warmed
  2. stirringstirred at room temperature for 16 h
  3. customthe organic phase was separated off
  4. extractionThe aqueous phase was extracted with ethyl acetate (4×50 ml)
  5. washthe combined organic phases were washed with sat. NaHCO3 solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe reaction product was used without further purification for the next reaction step

Sources & evidence

ORD record
ord-7a107e1d5fab4b2fad6d6a6daa41f6da
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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