Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Methylpropanimidamide hydrochloride | HCID 2782053 | — |
| Reactant | 2-Bromo-3-methoxycyclopent-2-enone | HCID 11095426 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58460155 | HCID 58460155 | 61.8% |
Reaction Steps
A mixture of 2-methylpropanimidamide hydrochloride (0.770 g), 2-bromo-3-(methyloxy)-2-cyclopenten-1-one (1 g) and potassium carbonate (2.17 g) in N,N-dimethylformamide (15 mL) were heated at 100° C. for 4.5 hr and then heated at 110° C. for 1 hour. The reaction mixture was cooled down to room temperature and dichloromethane was added. The white suspension (potassium carbonate) was filtered off and the filtrate concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile—0.1% NH3:water—with an ammonium carbonate buffer modifier using a 5%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (531 mg). LC/MS MH+ 165, Rt 0.36 min (2 minute run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399444B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-a7c1179e11c4404693992c6538ba499e |
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| Source note | uspto-grants-2013_03 |
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