Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Indanone | HCID 11983 | — |
| 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 | 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide | HCID 66743013 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Solvent | Tetrahydrofuran ethyl acetate | HCID 21939870 | — |
| Product | HCID 66743997 | HCID 66743997 | 12.5% |
Reaction Steps
A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene -2-carboxamide (111 mg, 0.50 mmol), 2-indanone (330 mg, 2.50 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.6 mg, 0.050 mmol) and DMA (3 mL) was stirred at 80° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and 2:1 EtOAc/THF. The organic layer was collected, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc, then to 90:10 EtOAc/MeOH), then triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (21 mg, 12%) as a beige solid:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08691828B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-efcfcc97929b4f63be0e947ab51dd6f2 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
