HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 60026306, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1,1,3,3-Tetramethylguanidine | HCID 66460 | — |
| Reactant | HCID 86600089 | HCID 86600089 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 60026306 | HCID 60026306 | 18% |
Reaction Steps
A solution of N-{5-cyano-2-[4-hydroxy-6-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-ynyl]-3-methylphenyl}-2,2,2-trifluoroacetamide (154 mg, 0.25 mmol) in 0.6 mL of anhydrous DMSO was heated in the presence of 1,1,3,3-tetramethylguanidine (0.094 mL, 0.75 mmol) in a microwave at 140° C. for 10 minutes. The reaction was quenched with a mixture of 1 N sulfuric acid and 10 mL of crushed ice. The resulting precipitate was filtered, washed with water, and dried. Preparative TLC chromatography (50% ethyl acetate in hexanes, followed by 15% ethyl acetate in dichloromethane) gave 23 mg of the title product as an off-white solid (18% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08741897B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-dac6812f74054170ace9a892b9dab524 |
| Source note | uspto-grants-2014_06 |