Acetonitrile → 1-(2,4-Dichlorophenyl)-7-(diethylamino)-2,3-dihydro-1H-[1,3]diazepino[1,2-a]benzimidazol-4(5H)-one

HRID 1628656Notes

Reaction equation

HRID 1628656 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:18]=3[N:14]2[CH2:13][CH:12]([OH:28])[CH2:11][CH2:10]1.C(#N)C>O.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:18]=3[N:14]2[CH2:13][C:12](=[O:28])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 577858071-(2,4-Dichlorophenyl)-7-(diethylamino)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-4-ol

Product 1

HCID 577862711-(2,4-Dichlorophenyl)-7-(diethylamino)-2,3-dihydro-1H-[1,3]diazepino[1,2-a]benzimidazol-4(5H)-oneYield 44.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-(2,4-dichlorophenyl)-7-(diethylamino)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-4-ol (Example 70; 60.0 mg, 0.143 mmol), tetra-n-propylammonium perruthenate (5.0 mg, 0.014 mmol), 4-methylmorphorine N-oxide (41.9 mg, 0.358 mmol), molecular sieves 4A (60 mg) and acetonitrile (1.5 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, filtered and extracted with ethyl acetate. The combined organic layer was washed with 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 10-30% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane to give the title compound as a solid (26.5 mg, 0.0635 mmol, 44%).

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture and recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-bfefd1cc2cc84247998517b63d8252f7
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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