Triethylamine → 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(5-benzyl-2,5-diazabicyclo(2.2.1)hept-2-yl)quinoline-3-carboxylic acid

HRID 727935

Reaktionsgleichung

Reaktionsgleichung von HRID 727935
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]2=[O:23].FOBOF.[CH2:29]([N:36]1[CH2:41][CH:40]2[CH2:42][CH:37]1[CH2:38][NH:39]2)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>CS(C)=O.CCOCC>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:39]1[CH2:38][CH:37]3[CH2:42][CH:40]1[CH2:41][N:36]3[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[N:8]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)[CH:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]2=[O:23]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 5629322-Benzyl-2,5-diazabicyclo[2.2.1]heptaneHCID 104486226,7-Difluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 178506430HCID 178506430, Verbindung

Produkt 1

HCID 140148236-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(5-benzyl-2,5-diazabicyclo(2.2.1)hept-2-yl)quinoline-3-carboxylic acidAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 1.5 g (4 m Mol) of the mixed anhydride of 6,7-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid with difluoroboronic acid in 10 ml of dimethylsulfoxide was added 0.9 g (4.78 m Mol) 2-benzyl-2.5-diazabicyclo(2.2.1)heptane and 0.4 g (4 m Mol) of triethylamine. After stirring for 4 hrs at room temperature, 150 ml of ether was added and the crystals that formed were collected by filtration. The residue was heated in a mixture of 60 ml dioxane and 90 ml 1.5N NaOH and heated at 100° C. for 1 hr. The hot solution was filtered to removed non-dissolved material. The solution was neutralized with conc HCl and the resultant crystals collected, washed with water and left to dry in the air. After recrystallization from DMF, 1.23 g (63%) of the product was obtained, mp 275° -280° dec.

Aufarbeitung

  1. customthe crystals that formed
  2. filtrationwere collected by filtration
  3. temperatureThe residue was heated in a mixture of 60 ml dioxane and 90 ml 1.5N NaOH
  4. temperatureheated at 100° C. for 1 hr
  5. filtrationThe hot solution was filtered
  6. customto removed non-dissolved material
  7. customthe resultant crystals collected
  8. washwashed with water
  9. waitleft
  10. customto dry in the air
  11. customAfter recrystallization from DMF

Quellen und Nachweise

ORD-Eintrag
ord-7473c576eeb74db383a97732f181e25b
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05045549

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