Reaktionsgleichung
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:13]=[N:14][C:9]2=[N:8][CH:7]=1)=[CH2:5])C.Cl>C(O)(=O)C>[N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH2:15][N:12]3[C:10]4=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][N:8]=[C:9]4[N:14]=[N:13]3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of the 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (150 mg, 0.451 mmol) in acetic acid, was added 3N HCl (0.1 mL). After the solution was stirred at rt for 2 h, solvents was removed under reduced pressure. The residue was diluted with water and its pH was adjusted to basic with aqueous NaHCO3, extracted with DCM. The combined organic layers were washed with NaHCO3(aq) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give a yellow solid of 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (131 mg, 91%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.45 (s, 1H), 8.95 (d, 1H), 8.14 (m, 2H), 7.95 (s, 1H), 7.84 (d, 1H), 7.45 (m, 1H), 6.19 (s, 2H), 2.75 (s, 3H). LCMS (method B): [MH]+=305, tR=2.95 min.
Aufarbeitung
- customsolvents was removed under reduced pressure
- additionThe residue was diluted with water and its pH
- extractionextracted with DCM
- washThe combined organic layers were washed with NaHCO3(aq) and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-b86a5ba8604544a4a2fd897bc14af30c
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08497368B2
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