2-(5-amino-1,3-dihydrobenzimidazol-2-ylidene)-1-(3,5-difluorophenyl)-3-phenylpropane-1,3-dione → 1-(3,5-difluorophenyl)-2-[5-(methylamino)-1,3-dihydrobenzimidazol-2-ylidene]-3-phenylpropane-1,3-dione

HRID 1061561Notes

Reaction equation

HRID 1061561 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7](=[C:9]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:21])[C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=3)=[O:11])[NH:8][C:4]=2[CH:3]=1.O[CH2:31]C1C2N=NNC=2C=CC=1>C(O)C>[F:18][C:16]1[CH:17]=[C:12]([C:10](=[O:11])[C:9](=[C:7]2[NH:6][C:5]3[CH:28]=[CH:29][C:2]([NH:1][CH3:31])=[CH:3][C:4]=3[NH:8]2)[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[CH:13]=[C:14]([F:19])[CH:15]=1

Participants

4

Reactant 2

HCID 1785072592-(5-amino-1,3-dihydrobenzimidazol-2-ylidene)-1-(3,5-difluorophenyl)-3-phenylpropane-1,3-dioneHCID 178519450HCID 178519450, compound

Product 1

HCID 1784820611-(3,5-difluorophenyl)-2-[5-(methylamino)-1,3-dihydrobenzimidazol-2-ylidene]-3-phenylpropane-1,3-dioneYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(5-amino-1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3,5-difluorophenyl)-3-phenylpropane-1,3-dione (400 mg) and ethanol (10 ml) was added hydroxymethylbenzotriazole (168 mg) at room temperature, and the reaction solution was stirred at room temperature for 20 hours. The reaction solution was filtered and the resulting solid matter was dissolved in THF (10 ml). Thereto was added sodium borohydride (78 mg) at room temperature and the reaction mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate (10 ml) and the organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (100:1 (v/v)) to obtain 1-(3,5-difluorophenyl)-2-[5-methylamino-1,3-dihydro-2H-benzimidazol-2-ylidene]-3-phenylpropane-1,3-dione (163 mg, 48%).

Workup

  1. filtrationThe reaction solution was filtered
  2. dissolutionthe resulting solid matter was dissolved in THF (10 ml)
  3. additionThereto was added sodium borohydride (78 mg) at room temperature
  4. stirringthe reaction mixture was stirred at room temperature for 3 hours
  5. additionThe reaction solution was diluted with ethyl acetate (10 ml)
  6. washthe organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washeluted with chloroform-methanol (100:1 (v/v))

Sources & evidence

ORD record
ord-02663d104f344714a6380dbc7d9c46a6
Source dataset
uspto-grants-2005_11
Patent number
US06960591B2

Reaction notes

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