HCID 59309864, compound → HCID 59309922, compound

HRID 1513051Notes

Reaction equation

HRID 1513051 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([CH2:32][OH:33])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:34]>CN(C)C=O.C(OCC)(=O)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([CH:32]=[O:33])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:34]

Participants

5

Reactant 1

HCID 59309864HCID 59309864, compound

Product 1

HCID 59309922HCID 59309922, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)-phenyl]-5-hydroxymethyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (15 mg) in N,N-dimethylformamide (1 mL) was added manganese(IV) oxide (0.3 g), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=2/3) to give the title compound (12 mg).

Workup

  1. customthe insoluble material was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-81d564fe610a4b75aa0e0edb3ee25500
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

Loading…