Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Chloromethyl)-5-(2-chlorophenyl)-1,3,4-oxadiazole | HCID 7131052 | — |
| Reactant | 5-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | HCID 59536836 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67412781 | HCID 67412781 | — |
Reaction Steps
85 mg (0.28 mmol) of the compound from Example 5A were dissolved in 5 ml of acetonitrile, and 180 mg (0.55 mmol) of cesium carbonate and 66 mg (0.29 mmol) of 2-(chloromethyl)-5-(2-chloro-phenyl)-1,3,4-oxadiazole were added. The mixture was stirred at 80° C. for 1 h. For work-up, the mixture was cooled to RT, and 10 ml of water were added. The mixture was extracted twice with in each case 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 66 mg (48% of theory) of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09187466B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-9cee89d3222546e0bcaacfe887d45ced |
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| Source note | uspto-grants-2015_11 |
|---|
