Sodium Hydroxide → 3-(5,6,7,8-Tetrahydroquinol-8-yl)propyl-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine
Reaktionsgleichung
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:7]([NH:19][CH2:20][CH2:21][CH2:22][CH:23]2[C:32]3[N:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][CH2:25][CH2:24]2)=[N:8][CH:9]=[C:10]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1.[OH-].[Na+]>O.S(=O)(=O)(O)O>[N:31]1[C:32]2[CH:23]([CH2:22][CH2:21][CH2:20][N:19]3[C:7]4=[N:8][CH:9]=[C:10]([CH2:12][C:13]5[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=5)[CH:11]=[C:6]4[N:5]=[N:1]3)[CH2:24][CH2:25][CH2:26][C:27]=2[CH:28]=[CH:29][CH:30]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 4 °C
Versuchsvorschrift
Sodium nitrite (1.3 g) in water (60 ml) was added over 25 minutes to a solution of 3-amino-2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino]-5-(pyrid-3-ylmethyl)pyridine (5.5 g) in molar sulphuric acid (250 ml) stirred at 4° C. The reaction mixture was stirred at 4° C. for 50 minutes, then allowed to warm to room temperature, basified with 10 molar sodium hydroxide solution to pH 13 and extracted with chloroform (3×150 ml). The chloroform extracts were combined, dried over magnesium sulphate, and the solvent removed to give a brown oil (6.04 g). The oil was chromatographed on silica in 5% MeOH/chloroform to give the title compound as an oil (3.61 g).
Aufarbeitung
- stirringThe reaction mixture was stirred at 4° C. for 50 minutes
- temperatureto warm to room temperature
- extractionextracted with chloroform (3×150 ml)
- dry with materialdried over magnesium sulphate
- customthe solvent removed
Quellen und Nachweise
- ORD-Eintrag
- ord-b5047853a49f454caf544f7cb1451faa
- Quelldatensatz
- uspto-grants-1988_08
- Patentnummer
- US04764519
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