Potassium Carbonate → HCID 58896435, compound

HRID 2235570Notes

Reaction equation

HRID 2235570 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:6]([OH:8])[CH:7]=1.C(=O)(O)[O-].[Cs+].Br[CH2:33][C:34]#[N:35].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:6]([CH:7]=1)[O:8][CH2:33][C:34]#[N:35]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile2×HCID 2734983Cesium bicarbonateHCID 58896585HCID 58896585, compound

Product 1

HCID 58896435HCID 58896435, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 48 mg (0.40 mmol) of 5-chloro-2-(7-dipropylamino-1-methyl-1H-benzimidazol-2-ylamino)phenol in 5 mL of tetrahydrofuran was added 114 mg (0.59 mmol) of cesium bicarbonate and 50 mg (0.41 mmol) of bromoacetonitrile and the reaction was stirred overnight at room temperature. Bromoacetonitrile, 200 mg (1.64 mmol), was added to the reaction and the mixture was stirred several hours at room temperature. Then 50 mg (0.36 mmol) of potassium carbonate was added to the reaction and it was stirred at room temperature overnight. The reaction was concentrated in vacuo to a residue that was dissolved in dichloromethane, washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with a solution of 20% ethyl acetate/hexanes to give 64 mg (58%) of the title compound.

Workup

  1. stirringthe mixture was stirred several hours at room temperature
  2. stirringwas stirred at room temperature overnight
  3. concentrationThe reaction was concentrated in vacuo to a residue that
  4. dissolutionwas dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by flash chromatography
  10. washeluting with a solution of 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6063c43cf83b450f95a7e2f108d2d8a1
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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