Methyl morpholine oxide → HCID 178519309, compound

HRID 2099858Notes

Reaction equation

HRID 2099858 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-9a56a8d89079483d94ed9d258cb81d4d
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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