HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 178465658, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethanimidic acid, ethyl ester, hydrochloride (1:1) | HCID 2724290 | — |
| Reactant | (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide | HCID 67035490 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tetrahydrofuran N,N-dimethylformamide | HCID 21974620 | — |
| Product | HCID 178465658 | HCID 178465658 | 73.9% |
Reaction Steps
To a stirred suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.062 g, 0.14 mmol) in 2:1 THF-DMF (1.5 mL) was added triethylamine (0.026 mL, 0.19 mmol), followed by ethyl acetimidate hydrochloride (0.021 g, 0.17 mmol) at 0° C. The mixture was allowed to warm up to ambient temperature and stirring continued at 60° C. for 5 hours. The mixture was poured into water, neutralized with 1N HCl, extracted with EtOAc, dried (phase separator silicone treated filter paper) and concentrated to give (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N′-(1-iminoethyl)benzohydrazide (0.049 g, 72% yield) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08865726B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-8c9673b8324747f68f3f77cfb3c15f6d |
| Source note | uspto-grants-2014_10 |