Tetrahydrofuran → 4-(4-Methylpiperazin-1yl)indole-2-carboxylic acid
Reaktionsgleichung
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].O1CCCC1>O>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[CH2:16][CH2:17]1Komponenten
Versuchsvorschrift
A solution of 1-(2-(ethoxycarbonyl)-1H-indol-4-yl)-4-methylpiperazine (0.91 g, 3.17 mmol), lithium hydroxide hydrate (0.136 g, 3.17 mmol, 1.0 equivalent), tetrahydrofuran (20 mL), and water (4 mL) was heated at reflux under nitrogen for 16 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was chromatographed using silica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2] to afford the title compound (0.40 g, 1.54 mmol, 49%) as a white solid: mp, 272-273° C.; R, =0.05 in methylene chloride/methanol/ammonium hydroxide [5:1:0.1]; 13C NMR (D2O) δ169.4, 145.0, 137.5, 132.9, 124.7, 120.7, 108.2, 107.3, 103.7, 58.7, 53.7, 51.0; LRMS (m/z, relative intensity) 260 (18), 259 (M+, 100), 244 (9), 215 (7), 170 (24); HRMS calculated for C14H17N3O2 259.1322, found 259.1325.
Aufarbeitung
- temperatureat reflux under nitrogen for 16 hours
- customThe resulting reaction mixture
- customwas evaporated under reduced pressure
- customthe residue was chromatographed
- washsilica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2]
Quellen und Nachweise
- ORD-Eintrag
- ord-e5ceba4b334244c2ab903fb48b9be35a
- Quelldatensatz
- uspto-grants-2001_07
- Patentnummer
- US06255306B1
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