HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl 4-{[cyclopentyl(4-{[2-(2-methylpropyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]-methyl}phenyl)acetyl]amino}-2,3-dihydro-1H-indene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(2-methylpropyl)-4H-1,3,4-oxadiazin-5(6H)-one | HCID 58136558 | — |
| Reactant | Methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate | HCID 58136756 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 4-{[cyclopentyl(4-{[2-(2-methylpropyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]-methyl}phenyl)acetyl]amino}-2,3-dihydro-1H-indene-2-carboxylate | HCID 58136403 | — |
Reaction Steps
100 mg (0.213 mmol) of methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate were dissolved in 3.5 ml of DMF, and 55 mg (0.213 mmol) of 2-(2-methylpropyl)-4H-1,3,4-oxadiazin-5(6H)-one (Example 22A) and 76 mg (0.234 mmol) of cesium carbonate were added. The reaction mixture was stirred at room temperature for 3 d. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by preparative HPLC. This gave 8 mg (8% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987256B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-7917be37c8f54eeaaedb1a901b0bb836 |
| Source note | uspto-grants-2015_03 |