Triethylammonium → 2-(5-Chlorobenzo[b]thiophen-3-ylmethyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic Acid
Reaktionsgleichung
C(N1C2C(=CC=C3C=2NC(=O)C3=O)CC1)(=[O:3])C.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]3[CH2:30][CH2:29][CH2:28][CH2:27][C:25]3=2)[C:20](=O)[C:19]1=[O:32].C([O:36][CH2:37][C:38](=O)[CH2:39][C:40]1[C:41]2[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:42]=2[S:43][CH:44]=1)(=O)C.C([NH+](CC)CC)C>>[Cl:49][C:47]1[CH:46]=[CH:45][C:42]2[S:43][CH:44]=[C:40]([CH2:39][C:38]3[C:37]([OH:36])=[C:20]([C:19]([OH:32])=[O:3])[C:21]4[C:26](=[C:25]5[CH2:27][CH2:28][CH2:29][CH2:30][C:24]5=[CH:23][CH:22]=4)[N:18]=3)[C:41]=2[CH:48]=1Komponenten
Edukt 4
Produkt 1
Versuchsvorschrift
The procedure described above for the synthesis and purification of compound 7 was followed, reacting 6,7,8,9-tetrahydrobenzo[g]indoline-2,3-dione (0.200 g, 0.994 mmol) with 3-(5-chlorobenzo[b]thiophen-3-yl)-2-oxopropyl acetate (0.365 g, 1.29 mmol). It was not possible to convert the triethylammonium salt obtained by preparative HPLC (basic modifier) back to the free acid by the usual method. Thus, the final product, a sunflower-yellow powder, was a triethylammonium salt with 6:5 acid:base stoichiometry (108 mg, 21% yield): 1H NMR (400 MHz, DMSO-d6) δ 1.17 (t, J=7.2 Hz, 7.5H) 1.72-1.87 (m, 4H) 2.77 (t, J=5.9 Hz, 2H) 3.10 (dq, 5H) 3.18 (t, J=5.7 Hz, 2H) 4.46 (s, 2H) 7.08 (d, J=8.8 Hz, 1H) 7.35 (dd, J=8.7, 2.2 Hz, 1H) 7.59 (s, 1H) 7.96 (d, J=8.3 Hz, 1H) 8.41 (d, J=2.1 Hz, 1H) 8.94 (d, J=8.8 Hz, 1H); HRMS (ESI+) calcd for C23H19ClNO3S (MH+) 424.0769, found 424.0770. Anal. Calcd for [C23H19ClNO3S]6[C6H15N]5[H2O]: C, 65.60; H, 5.78; N, 4.72. Found: C, 64.75; H, 6.01; N, 4.56.
Aufarbeitung
- customobtained by preparative HPLC (basic modifier) back to the free acid by the usual method
Quellen und Nachweise
- ORD-Eintrag
- ord-c4f78ea156ec451f9ab3529f9123e9e0
- Quelldatensatz
- uspto-grants-2008_12
- Patentnummer
- US07465798B2
Notizen zur Reaktion
Wird geladen…