Reaktionsgleichung
Cl[C:2]1[C:3]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH2:10]2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:23]1[CH2:28][CH2:27][CH:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+].CC(O)C>O>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[N:11]1[CH2:12][CH:9]([O:8][C:3]2[C:2]([N:23]3[CH2:28][CH2:27][CH:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]3)=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:10]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
To a mixture of 2-(3-((3-chloropyrazin-2-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.6; 312 mg, 1.0 mmol) and 1-(piperidin-4-yl)ethanone (127 mg, 1.0 mmol) and K2CO3 (276 mg, 2.0 mmol) was added i-PrOH (3 mL) and water (1.0 ml). The solution was heated to 160° C. under microwave for 5 hours. Then the mixture was concentrated and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in petroleum ether) to give the title product (72 mg, 0.18 mmol, 18% yield) as white solid. ESI-MS (M+1): 404 calc. for C23H25N5O2 403.
Aufarbeitung
- concentrationThen the mixture was concentrated
- extractionextracted with EtOAc (2×30 mL)
- washThe combined organic extracts were washed with water (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in petroleum ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-174739225df4471ea145f2c522cd939e
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08497265B2
Verknüpfte Notizen
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