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

HRID 2375572
Notes
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Reaction equation

HRID 2375572 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c4f78ea156ec451f9ab3529f9123e9e0
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07465798B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes