Trifluoroacetic anhydride → 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide

HRID 82690Notes

Reaction equation

HRID 82690 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH2:14]([N:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][C:23]=2[CH3:25])[N:18]([C:26]2[CH:31]=[CH:30][C:29]([O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])=[CH:28][CH:27]=2)[C:17]1=[O:43])[CH3:15].OO.NC(N)=O.[Cl-].[Cl-].[Ca+2].C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:14]([N:16]1[C:24]2[C:19](=[N+:20]([O-:4])[CH:21]=[CH:22][C:23]=2[CH3:25])[N:18]([C:26]2[CH:31]=[CH:30][C:29]([O:32][Si:33]([CH:34]([CH3:35])[CH3:36])([CH:37]([CH3:39])[CH3:38])[CH:40]([CH3:42])[CH3:41])=[CH:28][CH:27]=2)[C:17]1=[O:43])[CH3:15]

Participants

7

Reactant 5

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 585775691-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 585774851-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (3.92 mL) was added to a suspenstion of 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (4 g) and urea hydrogen peroxide (2.74 g) in EtOAc (20 mL) at 0° C. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) overnight. The mixture was neutralized with sat. NaHCO3 at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane) to give 1-ethyl-7-methyl-3-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 4-oxide (250 mg) as colorless crystals.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with 0%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-364ff1c68183439f8057608ecfd51366
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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