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Triethylamine → 5-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid

HRID 561155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561155
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][CH2:36][CH2:37][NH2:38].C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O.O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:38][CH2:37][CH2:36][NH:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:28])[C:5]([C:25]([OH:27])=[O:26])=[C:6]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[N:7]2[CH:16]1[CH2:18][CH2:17]1
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 590030445-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid

Produkt 1

HCID 590029455-Amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid
Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenylquinoline-3-carboxylic acid (550 mg, 1.42 mmol), N-2-pyridyl-1,2-ethanediamine (292 mg, 2.13 mmol) and triethylamine (0.297 mL, 2.13 mmol) in DMSO (7 mL) was stirred at 120° C. for 6 h. To the reaction mixture, water and NH4Cl was added to neutralize and the suspension was stirred for 30 min. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 1:1→1:5) to yield 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-2-phenyl-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (356 mg, 50%) as a yellow solid.

Aufarbeitung

  1. extractionThe crude product was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography (Hexane:EtOAc 1:1→1:5)

Quellen und Nachweise

ORD-Eintrag
ord-cbf9c7b543704a48aa1f0474aa8aea0c
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063221B2

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