Water → HCID 58577482, compound

HRID 82685Notes

Reaction equation

HRID 82685 reaction equation
[N:1]1([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[NH:21][C:20]3=[O:28])=[CH:15][CH:14]=2)[C:5]2=[N:6][C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[N:4]2[CH2:3][CH2:2]1.I[CH2:30][CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[N:1]1([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]([CH2:30][CH3:31])[C:20]3=[O:28])=[CH:15][CH:14]=2)[C:5]2=[N:6][C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[N:4]2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 58577570HCID 58577570, compound

Product 1

HCID 58577482HCID 58577482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-[4-(2,3-dihydro-1H-imidazo[2′,1′:2,3]imidazo[4,5-b]pyridin-1-yl)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (165 mg), iodoethane (0.054 mL) and cesium carbonate (291 mg) in DMF (3 mL) was stirred at 50° C. for 6 h. The mixture was poured into water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residual crystals were dissolved in THF, and the solution was filtered through NH-silica gel. The filtrate was concentrated under reduced pressure. The residual crystals were recrystallized from EtOH to give the title compound (94 mg).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residual crystals were dissolved in THF
  7. filtrationthe solution was filtered through NH-silica gel
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residual crystals were recrystallized from EtOH

Sources & evidence

ORD record
ord-090b79ab17db4cf48dd710b29db70e47
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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