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1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(trans-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580596
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 580596
[Br:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C(OC([NH:28][C@H:29]1[C@H:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:28][C@H:29]1[C@H:33]([CH3:34])[CH2:32][N:31]([C:3]2[C:2]([Br:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1
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Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137488068-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 53686699rac-tert-butyl N-[(3R,4S)-4-methylpyrrolidin-3-yl]carbamate

Produkt 1

HCID 703533807-(trans-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.11 g), trans-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.082 g), DBU (0.054 g) and anhydrous acetonitrile (5 ml) was refluxed for 1.5 hours and then concentrated. The resulting residue was dissolved in chloroform (50 ml) and washed with 10% aqueous citric acid solution and water successively. The organic layer was concentrated under reduced pressure and to the oily residue was added methanol to crystallize. The resulting precipitate was collected by filtration, washed with chilled methanol and this was added to concentrated hydrochloric acid-methanol (1:1, 2 ml) and stirred for an hour at room temperature. The reacting mixture was neutralized with concentrated aqueous ammonia, concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:concentrated aqueous ammonia=20:6:1) and then recrystallized from dichloromethanemethanol (1:1) to give the title compound (0.04 g) as pale yellow powder, mp 186°-190° C. (decompd.).

Aufarbeitung

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in chloroform (50 ml)
  4. washwashed with 10% aqueous citric acid solution and water successively
  5. concentrationThe organic layer was concentrated under reduced pressure and to the oily residue
  6. additionwas added methanol
  7. customto crystallize
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with chilled methanol
  10. additionthis was added to concentrated hydrochloric acid-methanol (1:1, 2 ml)
  11. concentrationconcentrated under reduced pressure
  12. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:concentrated aqueous ammonia=20:6:1)
  13. customrecrystallized from dichloromethanemethanol (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ba97b3bfde54e4db132c7fd7abc1202
Quelldatensatz
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04753953

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