Methyl morpholine oxide → HCID 178519309, compound

HRID 1061560Notes

Reaction equation

HRID 1061560 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:30])[C:10](=[C:19]2[NH:23][C:22]3[CH:24]=[CH:25][C:26]([CH2:28][OH:29])=[CH:27][C:21]=3[NH:20]2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.C[N+]1([O-])CCOCC1>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[C:9]([C:10](=[C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([CH:28]=[O:29])=[CH:27][C:21]=2[NH:20]1)[C:11](=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:30]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 178520873HCID 178520873, compound

Product 1

HCID 178519309HCID 178519309, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a dichloromethane solution (5 ml) of the compound (174 mg) obtained in Example 405 were added NMO (100 mg) and MS4A, followed by 10 minutes of stirring at room temperature. TPAP (8 mg) was further added thereto, followed by 30 minutes of stirring at room temperature. The reaction solution was purified by silica gel column chromatography (eluent: chloroform:methanol=40:1 (v/v)) to obtain 2-[1-(3,5-difluorobenzoyl)-2-oxo-2-phenylethylidene]-2,3-dihydro-1H-benzimidazol-5-carbaldehyde (76 mg, 44%).

Workup

  1. waitfollowed by 30 minutes
  2. stirringof stirring at room temperature
  3. customThe reaction solution was purified by silica gel column chromatography (eluent: chloroform:methanol=40:1 (v/v))

Sources & evidence

ORD record
ord-8c4b3d50771d464ea3b69a46aed2824d
Source dataset
uspto-grants-2005_11
Patent number
US06960591B2

Reaction notes

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