Potassium Hydroxide → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-carbamoyl-3-hydroxy-3-(2-naphthyl)oxindole
Reaktionsgleichung
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:2].[OH-:35].[K+]>C(O)(C)(C)C>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:18])([F:20])[F:19])[CH:11]=[C:12]([C:15](=[O:35])[NH2:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:34]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole of Example 55 (185 mg, 0.396 mmol) in t-butanol (8 mL) was added powdered KOH (ca. 1 g) at 50° C. The mixture was stirred for 1 h at 50° C. and passed through a celite pad. The celite was washed with THF and the filtrate was concentrated. The residue was dispersed between water and ethyl acetate and the organic layer was separated. The organic layer was dried over MgSO4 and concentrated to give the title compound (198 mg, quant.). The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.
Aufarbeitung
- washThe celite was washed with THF
- concentrationthe filtrate was concentrated
- additionThe residue was dispersed between water and ethyl acetate
- customthe organic layer was separated
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-34f43ebae4f749628982cb84de309431
- Quelldatensatz
- uspto-grants-2003_06
- Patentnummer
- US06576656B1
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