Triethylammonium → 2-(5-Chlorobenzo[b]thiophen-3-ylmethyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic Acid
반응식
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]=1참가 물질
반응물 4
생성물 1
실험 절차
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.
후처리
- customobtained by preparative HPLC (basic modifier) back to the free acid by the usual method
출처 및 근거
- ORD 기록
- ord-c4f78ea156ec451f9ab3529f9123e9e0
- 출처 데이터셋
- uspto-grants-2008_12
- 특허 번호
- US07465798B2
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