Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.CS(O)(=O)=O.N1C2C(=CC=CC=2)C=CC=1.[C:29](Cl)(Cl)=[O:30].C1(C)C=CC=CC=1.[CH3:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:57])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[NH2:56])=[CH:44][CH:43]=1>C(Cl)Cl>[CH3:40][O:41][C:42]1[CH:43]=[CH:44][C:45]([NH:48][C:49](=[O:57])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[NH:56][C:29]([O:13][CH:10]2[CH2:11][CH2:12][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:8][CH2:9]2)=[O:30])=[CH:46][CH:47]=1Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a mixture of 1-(4-pyridyl)-4-hydroxypiperidine (536 mg, 3.01 mmol) and methylene chloride (45 mL) was added methanesulfonic acid (0.2 ml, 3.1 mmol). After stirring for 15 seconds, quinoline (0.45 mL, 3.8 mmol) was added, immediately followed by 1.93 M phosgene in toluene (2 mL, 3.9 mmol). After 5 minutes, the reaction was placed in a 35° C. oil bath for 45 minutes. The reaction was cooled to room temperature and N-(4-methoxyphenyl)-2-aminobenzamide (728 mg, 3.0 mmol) and quinoline(0.45 mL, 3.8 mmol) were added. After stirring overnight, the reaction was diluted with CH2Cl2(150 mL) and washed with sat'd sodium carbonate (2×25 mL). The organic layer was concentrated and the crude residue was chromatographed to give 617 mg (46%) of the title compound as a white solid.
Aufarbeitung
- waitAfter 5 minutes
- customwas placed in a 35° C.
- customfor 45 minutes
- stirringAfter stirring overnight
- washwashed with sat'd sodium carbonate (2×25 mL)
- concentrationThe organic layer was concentrated
- customthe crude residue was chromatographed
Quellen und Nachweise
- ORD-Eintrag
- ord-2df88400879e4876b1fd1e7676a166ee
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06605626B2
Verknüpfte Notizen
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