7-Aminoquinoline → 9-Oxo-9H-fluorene-2-carboxylic acid quinolin-7-yl amide

HRID 494258

Reaktionsgleichung

Reaktionsgleichung von HRID 494258
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[O:12]=[C:13]1[C:25]2[CH:24]=[C:23]([C:26](O)=[O:27])[CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:26]([C:23]3[CH:22]=[CH:21][C:20]4[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:13](=[O:12])[C:25]=4[CH:24]=3)=[O:27])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 113777-AminoquinolineHCID 69913Fluorenone-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 576826739-Oxo-9H-fluorene-2-carboxylic acid quinolin-7-yl amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-aminoquinoline (D55) (35 mg, 0.24 mmol) in DCM (3 ml) was added 9-oxo-9H-fluorene-2-carboxylic acid (60 mg, 0.27 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (68 mg, 0.36 mmol) and 4-dimethylaminopyridine (5 mg, 0.04 mmol) and the reaction stirred at room temperature then at reflux until complete by tlc. After cooling to room temperature the resultant precipitate was filtered off to give the title compound as an off-white solid. MS(ES): MH+ 351, M-H+ 349

Aufarbeitung

  1. temperatureat reflux until complete by tlc
  2. filtrationwas filtered off

Quellen und Nachweise

ORD-Eintrag
ord-e46a805cfcff40e3a1a945274cb69073
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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