Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopentanone | HCID 8452 | — |
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66743701 | HCID 66743701 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 66743184 | HCID 66743184 | 56% |
Reaction Steps
A mixture of 5-bromo-3-(ethylamino)thiophene-2-carboxamide (500 mg, 2.0 mmol), cyclopentanone (0.53 mL, 6.0 mmol), CSA (46 mg, 0.20 mmol), MgSO4 (384 mg, 4.0 mmol) and DMA (1.5 mL) was stirred at 90° C. for 1 day. The mixture was poured into saturated aqueous NaHCO3. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 50:50 hexane/EtOAc) to give a brown solid. The solid was washed with EtOAc to give the title compound (352 mg, 56%) as a pale brown solid:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08691828B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-c5a90e1123274a33af7521819fb29104 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
