Potassium Carbonate → HCID 66754935, compound

HRID 1643956Notes

Reaction equation

HRID 1643956 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8]N(C)C.Cl.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[NH:21][C:20](=[O:22])[N:19]([CH:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]([OH:26])=O)[C:18]=2[CH:33]=1.C1C=CC2N(O)N=NC=2C=1.[N:44]1[CH:49]=[CH:48][C:47]([N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)=[CH:46][CH:45]=1.[CH2:56](N(C(C)C)C(C)C)C.[C:65](=[O:68])([O-])[O-:66].[K+].[K+]>ClCCl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[NH:21][C:20](=[O:22])[N:19]([CH:23]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:24]([N:53]3[CH2:52][CH2:51][N:50]([CH:47]4[CH2:48][CH2:49][N:44]([C:65]([O:66][C:7]([CH3:8])([CH3:56])[CH3:6])=[O:68])[CH2:45][CH2:46]4)[CH2:55][CH2:54]3)=[O:26])[C:18]=2[CH:33]=1

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 705171-(4-Pyridyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66754875HCID 66754875, compound

Product 1

HCID 66754935HCID 66754935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.99 mg (1.56 mmol) of EDCl were added to a solution of 430 mg (1.42 mmol) of (6-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid (VIIIa), 289 mg (2.13 mmol) of HOBt, 459 mg (0.1.70 mmol) of 1-pyridin-4-ylpiperazine and 1.24 ml (7.10 mmol) of ethyldiisopropylamine in dichloromethane (25 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: 439 mg (56%) of white 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-4cd00e870ffc4e0c81a94e6b252472fc
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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