HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]imidazolidin-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 66687731 | HCID 66687731 | — |
| Reactant | 1-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid | HCID 89602457 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]imidazolidin-4-one | HCID 86574307 | — |
Reaction Steps
0.12 ml (0.70 mmol) of N,N-diisopropylethylamine is added to a solution of 220 mg (0.23 mmol, 37% purity) of the compound of Example 64A, 57 mg (0.47 mmol) of 4-imidazolinone-hydrochloride, and 142 mg (0.38 mmol) of HATU in 6 ml of THF, and the mixture that is obtained is stirred for 20 hours at room temperature. After the further addition of 57 mg (0.47 mmol) of 4-imidazolinone-hydrochloride as well as 89 mg (0.23 mmol) of HATU, stirring is continued for 16 hours at 60° C. The crude product is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 39 mg (35% of theory, 88% purity) of the title compound is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09296720B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-ca77122bd8e942f8ad3710f0250277fe |
| Source note | uspto-grants-2016_03 |