Dimethylformamide → HCID 59309867, compound

HRID 1513059Notes

Reaction equation

HRID 1513059 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([S:10]([C:13]([CH3:21])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])(=[O:12])=[O:11])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([CH2:33][OH:34])=[CH:29][C:30]([O:31][CH3:32])=[C:25]2[NH:24][C:23]1=[O:35].CN(C)C=[O:39]>C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[C:33]([C:28]1[N:27]=[C:26]2[N:22]([C:3]3[CH:4]=[C:5]([S:10]([C:13]([CH3:21])([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH3:14])(=[O:12])=[O:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=3[Cl:1])[C:23](=[O:35])[NH:24][C:25]2=[C:30]([O:31][CH3:32])[CH:29]=1)([OH:39])=[O:34]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 59309746HCID 59309746, compound

Product 1

HCID 59309867HCID 59309867, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-chloro-4-methoxy-5-(1-methyl-1-phenylethylsulfonyl)-phenyl]-5-hydroxymethyl-7-methoxy-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (40 mg) in N,N-dimethylformamide (2 mL) was added manganese(IV) oxide (0.4 g), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was diluted with ethyl acetate, and the insoluble material was removed by filtration. The filtrate was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue were added tert-butanol (1.5 mL), water (0.15 mL), sodium dihydrogen phosphate dihydrate (10 mg), 2-methyl-2-butene (18 mg) and a solution of sodium chlorite (20 mg) in water (0.3 mL) successively, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture were added 1 mol/L hydrochloric acid and water, and the precipitated crystals were collected by filtration. The collected crystals were washed with water, and dried under reduced pressure to give the title compound (19 mg).

Workup

  1. customthe insoluble material was removed by filtration
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. additionTo the residue were added tert-butanol (1.5 mL), water (0.15 mL), sodium dihydrogen phosphate dihydrate (10 mg), 2-methyl-2-butene (18 mg)
  6. stirringa solution of sodium chlorite (20 mg) in water (0.3 mL) successively, and the mixture was stirred at room temperature for 3 hours
  7. additionTo the reaction mixture were added 1 mol/L hydrochloric acid and water
  8. filtrationthe precipitated crystals were collected by filtration
  9. washThe collected crystals were washed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-e6b6f092fc984dcfad9f96b80d898bbb
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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