Diisopropylethylamine → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534822
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Br.Br.[C:22]12[CH2:29][NH:28][CH2:27][C:26]=1[CH2:25][NH:24][CH2:23]2.C(N(C(C)C)CC)(C)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:24]4[CH2:25][C:26]5[CH2:27][NH:28][CH2:29][C:22]=5[CH2:23]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Produkt 1

HCID 199082481-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.4 g) and 3,7-diazabicyclo[3.3.0] oct-1(5)-ene dihydrobromide (4.2 g) were added to diisopropyl ethylamine (11.6 ml) in acetonitrile (120 ml) and refluxed for 7 hours. The produced precipitate was filtered, washed with acetonitrile (100 ml), water (50 ml), ethanol (50 ml) and them ethyl ether (50 ml) to give the title compound (4.2 g, yield 77%).

Aufarbeitung

  1. temperaturerefluxed for 7 hours
  2. filtrationThe produced precipitate was filtered
  3. washwashed with acetonitrile (100 ml), water (50 ml), ethanol (50 ml) and them ethyl ether (50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-bf7be7dd5d854eccb4798dbbf45f1a84
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091384

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