Methyl morpholine oxide → HCID 58031560, compound

HRID 2067342Notes

Reaction equation

HRID 2067342 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]([OH:21])[CH2:19][N:18]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17]2=[O:29])=[N:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[C:20](=[O:21])[CH2:19][N:18]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:17]2=[O:29])=[N:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58031479HCID 58031479, compound

Product 1

HCID 58031560HCID 58031560, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2-[3-(4-fluorophenyl)-5-hydroxy-2-oxo-imidazolidin-1-yl]-4-methylthiazole-5-carboxylic acid benzylamide (0.07 g, 0.17 mmol) and tetrapropylammonium perruthenate (0.003 g, 0.008 mmol) in chloroform (15 mL) was added 4-methylmorpholine N-oxide (0.03 g, 0.22 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 1 hour, and filtered through a bed of celite. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography to afford the title compound in 18% yield (0.14 g): mp 217-219° C.; 1H NMR (300 MHz, CDCl3) δ 7.54-7.07 (m, 9H), 6.12 (t, J=5.1 Hz, 1H), 4.55 (d, J=5.1 Hz, 2H), 4.47 (s, 2H), 2.70 (s, 3H); MS (ES+) m/z 425.3 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a bed of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9f3308ea39034b208fca5c5a6f5df829
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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