1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 15859790, Verbindung

HRID 1603438

Reaktionsgleichung

Reaktionsgleichung von HRID 1603438
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][NH:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[C:18](F)=[C:19]([F:34])[CH:20]=[C:21]2[C:26]=1[N:25]([CH:27]1[CH2:29][CH2:28]1)[CH:24]=[C:23]([C:30]([OH:32])=[O:31])[C:22]2=[O:33].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][N:11]([C:18]1[C:17]([Cl:16])=[C:26]3[C:21]([C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24][N:25]3[CH:27]3[CH2:29][CH2:28]3)=[CH:20][C:19]=1[F:34])[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15859786tert-Butyl 3-azabicyclo[3.2.0]heptan-1-ylcarbamate

Produkt 1

HCID 15859790HCID 15859790, VerbindungAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.22 g of 1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]heptane, 0.96 g of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 0.58 g of 1,8-diazabicyclo[5.4.0]-7-undecene were added to 20 ml of acetonitrile, followed by heating under reflux for 3.5 hours. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (using a 100:1 mixture of chloroform and methanol as the eluent) and recrystallization (from ethyl acetate-diisopropyl ether) to obtain 0.96 g of 7-[1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]hept-3-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (m.p. 200-202° C.).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 3.5 hours
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (
  5. additiona 100:1 mixture of chloroform and methanol as the eluent) and
  6. customrecrystallization (from ethyl acetate-diisopropyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-a2656d546ec8415fb777bb28021c474b
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990106

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