Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[C:12]([NH:22][CH:23]([CH2:27]O)[CH:24]([CH3:26])[CH3:25])[N:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=[C:12]([N:22]2[CH:23]([CH:24]([CH3:26])[CH3:25])[CH2:27][O:8][CH:7]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:11]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Pyridine-2-carboxaldehyde (207 mg, 1.9 mmol) was added to a toluene solution (15 mL) of 2-chloro-6-[[1-(hydroxymethyl)-2-methyl-propyl]amino]-4-(trifluoromethyl)pyridine-3-carbonitrile (400 mg, 1.3 mmol) (Compound 13) followed by a catalytic amount of para-toluene sulfonic acid (50 mg). The reactants were refluxed for 6 hours in a Dean-Stark apparatus, concentrated under reduced pressure, adsorbed onto silica and purified using a neutral alumina column, eluting with a mobile phase of 10% ethyl acetate in hexane. 2-Chloro-6-[4-isopropyl-2-(2-pyridyl)oxazolidin-3-yl]-4-(tri fluoromethyl) pyridine-3-carbonitrile (Compound 12) was isolated as a solid in 20% yield. mp 112-115° C.
Aufarbeitung
- temperatureThe reactants were refluxed for 6 hours in a Dean-Stark apparatus
- concentrationconcentrated under reduced pressure
- custompurified
- washeluting with a mobile phase of 10% ethyl acetate in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-d2ae51f8ab4a4568aa2e5328c1304ea5
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08604199B2
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