Sodium Hydroxide → 2-(1-methylethyl)cyclohepta[d]imidazol-4(1H)-one

Temperatur

30 °C

To a mixture of sodium hydroxide 30% in water (24 g) and toluene (30 mL), tropolone tosylate (5 g), isopropylcarbamidine hydrochloride (2.2 g) and tetrabutylammonium bromide (2.3 g) were added successively and the RM was stirred and heated at 30° C. for 1 hour. The reaction mixture was cooled down to room temp, diluted with an excess of sat. aq. NH4Cl solution and then extracted with EtOAc (3×40 ml). The aqueous phase was again extracted with EtOAc (3×50 ml). All the organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile-0.1% TFA:Water-0.1% TFA 5%-50% gradient and a 50%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (3.4 g). LC/MS MH+ 189, Rt 1.18 min (5 minute run)

1. additionwere added successively
2. temperatureThe reaction mixture was cooled down to room temp
3. extractionextracted with EtOAc (3×40 ml)
4. extractionThe aqueous phase was again extracted with EtOAc (3×50 ml)
5. customdried (hydrophobic frit)
6. concentrationconcentrated under vacuum
7. customThe residue was purified by reverse phase chromatography
8. concentrationconcentrated under vacuum

ORD-Eintrag

ord-e564a288b51141cbb929d70d96eb9aa7

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399444B2