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1,8-Diazabicyclo(5.4.0)undec-7-ene → (-)-9-Fluoro-3 (S)-methyl-10-[3-(1,2,3-triazol-1-yl) pyrrolidin-1-yl]-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3de]-1,4-benzoxazine-6-carboxylic acid

HRID 1742962
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1742962
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.Cl.[N:22]1([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[CH:26]=[CH:25][N:24]=[N:23]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:1][C:2]1[C:3]([N:29]2[CH2:30][CH2:31][CH:27]([N:22]3[CH:26]=[CH:25][N:24]=[N:23]3)[CH2:28]2)=[C:4]2[O:9][CH2:8][C@H:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23
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Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 688333Levofloxacin q-acidHCID 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Produkt 1

HCID 70283859(-)-9-Fluoro-3 (S)-methyl-10-[3-(1,2,3-triazol-1-yl) pyrrolidin-1-yl]-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3de]-1,4-benzoxazine-6-carboxylic acidAusbeute 9,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a suspension of 76 mg (0.27 mmol) of (-) -9,10-difluoro-3(S)-methyl-7-oxo-2,3-dihydro-7H -pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid and 118 mg (0.675 mmol) of 3-(1,2,3-triazol-1-yl) pyrrolidine hydrochloride in 10 ml of dry acetonitrile was added 121 mg (0.81 mmol) of DBU. The reddish brown solution was refluxed for 31 hr. The solvent was then removed under reduced pressure. To the residue water was added and extracted with chloroform. The organic layer was then evaporated to dryness, and to the residue, water was added and solid collected to yield 10 mg of the desired product, m.p. 225°-229° C. 1H NMR (TFA) δ: 9.17 (s, 1H), 8.67 (s, 1H), 8.57 (s, 1H), 7.99 (d, 13.3Hz, 1H), 5.9-5.18 (m, 1H), 5.22-4.07 (m, 7H), 3.13-2.63 (m, 2H), 1.82 (s, 3H), 1.79 (s, 3H). Anal. calcd. for C19H18N5O4F . 1/2 H2O: C, 55.86; H, 4.69; N, 17.16. Found: C, 55.93; H, 4.59; N, 16.37.

Aufarbeitung

  1. temperatureThe reddish brown solution was refluxed for 31 hr
  2. customThe solvent was then removed under reduced pressure
  3. additionTo the residue water was added
  4. extractionextracted with chloroform
  5. customThe organic layer was then evaporated to dryness
  6. additionto the residue, water was added
  7. customsolid collected

Quellen und Nachweise

ORD-Eintrag
ord-e2f2508567154e7e8b9bfdbae4d932bc
Quelldatensatz
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05342846

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