HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid monohydrate → 2-[5-(2,2-Dimethylpropoxy)pyridin-2-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | 5-(2,2-Dimethylpropoxy)-2-hydrazinopyridine | HCID 55279160 | — |
| Reactant | Ethyl 3-(N,N-dimethylamino)-2-(1H-imidazol-1-yl)acrylate | HCID 66726242 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 2-[5-(2,2-Dimethylpropoxy)pyridin-2-yl]-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one | HCID 59603695 | — |
Reaction Steps
233 mg (1.0 mmol, purity 90%) of the compound from Example 42A are initially introduced into 4 ml ethanol. 260 mg (1.0 mmol, purity 75%) of the compound from Example 12A and 38 mg (0.2 mmol) p-toluenesulfonic acid monohydrate are added and the mixture is stirred under reflux for 16 h. The mixture is then allowed to cool to RT, the solid which has precipitated out is filtered off and washed with a little ethanol and the solid is dried under a high vacuum. A further amount of the target compound is obtained by purifying the mother liquor of the filtration via preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09168249B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-2762d23f042f4e188186660d80796a95 |
| Source note | uspto-grants-2015_10 |