HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroform → 2-(4-{[2'-Methyl-4'-(pyrrolidin-1-ylcarbonyl)biphenyl-3-yl]methoxy}benzyl)-1,2,4-oxadiazolidine-3,5-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride | HCID 2734059 | — |
| Reactant | 3'-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2-methylbiphenyl-4-carboxylic acid | HCID 57787330 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | 2-(4-{[2'-Methyl-4'-(pyrrolidin-1-ylcarbonyl)biphenyl-3-yl]methoxy}benzyl)-1,2,4-oxadiazolidine-3,5-dione | HCID 57787836 | 67.6% |
Reaction Steps
3′-({4-[(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)methyl]phenoxy}methyl)-2-methylbiphenyl-4-carboxylic acid (10.8 mg) was dissolved in a THF-methanol [1 ml, 4:1 (v/v)] mixed solution, and the solution was added to pyrrolidine (3.2 mg). DMT-MM (12 mg) was added, followed by overnight stirring at room temperature. Thereafter, chloroform was added to the reaction liquid, and the organic layer was washed with 1 M hydrochloric acid. The organic layer was concentrated, and the residue was purified by a fractional HPLC (Waters, product name: Waters SunFire™ Prep C18OBD™ (19×100 mm, 5 μm)) to obtain 2-(4-{[2′-methyl-4′-(pyrrolidin-1-ylcarbonyl)biphenyl-3-yl]methoxy}benzyl)-1,2,4-oxadiazolidine-3,5-dione (8.2 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07968552B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-968a777ba3ed4f92954b33a8426184e0 |
| Source note | uspto-grants-2011_06 |