Potassium Carbonate → HCID 58460160, compound

Temperature

100 °C

A mixture of cyclopropanecarboximidamide hydrochloride (0.757 g), 2-bromo-3-(methyloxy)-2-cyclopenten-1-one (1 g) and potassium carbonate (2.171 g) in N,N-dimethylformamide (15 mL) were heated at 100° C. for 3 h. Potassium carbonate (1 g) was added and the mixture heated at 110° C. for further 16 h. The reaction mixture was cooled down to room temperature and partitioned between dichloromethane (60 mL) and sat. aq. NH4Cl (60 mL). The 2 phases were separated, the aqueous was extracted with DCM (2×40 mL), the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient with a 0->20% Ethyl Acetate-MeOH wash at the end. The desired fractions (in the MeOH wash) were combined and concentrated under vacuum to give the title compound (272 mg), used crude in the next reaction. LC/MS MH+ 163, Rt 1.45 min (5 minute run).

1. temperaturethe mixture heated at 110° C. for further 16 h
2. temperatureThe reaction mixture was cooled down to room temperature
3. custompartitioned between dichloromethane (60 mL) and sat. aq. NH4Cl (60 mL)
4. customThe 2 phases were separated
5. extractionthe aqueous was extracted with DCM (2×40 mL)
6. customdried (hydrophobic frit)
7. concentrationconcentrated under vacuum
8. customThe residue was purified on silica using a cyclohexane
9. washethyl acetate 0-100% gradient with a 0->20% Ethyl Acetate-MeOH wash at the end
10. washThe desired fractions (in the MeOH wash)
11. concentrationconcentrated under vacuum

ORD record

ord-a34dd65c861b423bab6d2b95849e9cae

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399444B2