Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 136149935 | HCID 136149935 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 136150022 | HCID 136150022 | 41.8% |
Reaction Steps
100 mg 5-[3-Methyl-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde and 12.8 mg propylamine were suspended in 3 ml methanol. 30.0 μl triethylamine were added upon the reaction mixture became a clear solution. 400 mg molecular sieves four angstrom were added and the reaction mixture stirred at room temperature for two hours. Then 8.2 mg sodium borohydride were added and the reaction mixture stirred at room temperature for thirty minutes. The reaction mixture was filtered through a celite pad. The filtrate was evaporated in vacuo and then evaporated in vacuo. The residue was purified by RP-HPLC to obtain 45.7 mg 3-{2-methyl-4-[4-propylaminomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one as its trifluoroacetate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07851493B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-a42296ba7d45472ea23a2de8a3c99a7b |
|---|
| Source note | uspto-grants-2010_12 |
|---|