HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(difluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate → 3-[5-(5-{3-Chloro-4-[(difluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(difluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate | HCID 58149927 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-[5-(5-{3-Chloro-4-[(difluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid | HCID 44476671 | 44.9% |
Reaction Steps
1,1-Dimethylethyl 3-[5-(5-{3-chloro-4-[(difluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D46; 32 mg, 0.064 mmol) was dissolved in 4M hydrogen chloride in 1,4-dioxane, and the solution allowed to stand at room temperature for 2 h. The solvent was evaporated in vacuo to give a white solid which was triturated under dry ether (3×5 ml) to give a white solid. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents NB (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)). The solvent was evaporated in vacuo to give the title compound as a white solid (12.8 mg)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08329730B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-c5e4fc2d480845419df1928780c234b2 |
| Source note | uspto-grants-2012_12 |