Triethylammonium → 2-(5-Chlorobenzo[b]thiophen-3-ylmethyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic Acid

HRID 2375572ノート

反応式

HRID 2375572 の反応式
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]=1

参加物

5

反応物 4

HCID 1385867TriethylammoniumHCID 137804146,7,8,9-Tetrahydro-1H-benzo[g]indole-2,3-dioneHCID 161000613-(5-Chlorobenzo[b]thiophen-3-yl)-2-oxopropyl acetateHCID 199196918-Acetyl-1,6,7,8-tetrahydro-1,8-diaza-as-indacene-2,3-dione

生成物 1

HCID 112587852-(5-Chlorobenzo[b]thiophen-3-ylmethyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic Acid収率 21%

実験手順

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.

後処理

  1. customobtained by preparative HPLC (basic modifier) back to the free acid by the usual method

出典と根拠

ORDレコード
ord-c4f78ea156ec451f9ab3529f9123e9e0
出典データセット
uspto-grants-2008_12
特許番号
US07465798B2

反応ノート

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