1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580569

Reaktionsgleichung

Reaktionsgleichung von HRID 580569
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[NH2:20][CH2:21][CH:22]1[CH:26]([CH3:27])[CH2:25][NH:24][CH2:23]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:20][CH2:21][CH:22]1[CH:26]([CH3:27])[CH2:25][N:24]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:15])[CH2:23]1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4583498(4-Methylpyrrolidin-3-yl)methanamineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Produkt 1

HCID 139330907-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-aminomethyl-4-methylpyrrolidine (0.22 g) and DBU (0.28 g) was refluxed for an hour and then stirred at room temperature for 3 hours. The resulting precipitate was collected by filtration and washed with ether to give the title compound (0.39 g) as pale yellow powder, mp 222°-224° C.

Aufarbeitung

  1. temperaturewas refluxed for an hour
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-4f53e47eedaa4744a3b0dfd901419858
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04753953

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