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 82690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82690
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]

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-364ff1c68183439f8057608ecfd51366
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846713B2

Notizen zur Reaktion

Wird geladen…