Water → (S)-9-Fluoro-3-Methyl-10-(4-Methylpiperazin-1-yl)-6-(5-oxo-4,5-Dihydro-1H-Tetrazol-1-yl)-2,3-Dihydro-7H-[1,4]Oxazino[2,3,4-IJ]Quinolin-7-One

HRID 59046

Reaction equation

HRID 59046 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][C@@H:19]1[N:40]2[C:23]3[C:24]([C:36]([C:38](C(O)=O)=[CH:39]2)=[O:37])=[CH:25][C:26]([F:35])=[C:27]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[C:22]=3[O:21][CH2:20]1.CC[N:46]([CH2:49]C)CC.[OH2:51]>C(Cl)Cl>[F:35][C:26]1[CH:25]=[C:24]2[C:23]3=[C:22]([O:21][CH2:20][C@H:19]([CH3:18])[N:40]3[CH:39]=[C:38]([N:15]3[C:49](=[O:51])[NH:46][N:17]=[N:16]3)[C:36]2=[O:37])[C:27]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 149096LevofloxacinHCID 199401P,P-Diphenylphosphinic azide2×

Product 1

HCID 137167451(S)-9-Fluoro-3-Methyl-10-(4-Methylpiperazin-1-yl)-6-(5-oxo-4,5-Dihydro-1H-Tetrazol-1-yl)-2,3-Dihydro-7H-[1,4]Oxazino[2,3,4-IJ]Quinolin-7-One

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Diphenyl phosphoryl azide (323 μL, 1.5 mmol) was added to a stirred solution of Levofloxacin (361 mg, 1.0 mmol) and Et3N (280 μL, 2.0 mmol) in CH2Cl2 (10 mL) at 0° C. under an atmosphere of nitrogen. The mixture was stirred at 0° C. for 15 min, then allowed to warm to room temperature and stirred for 4 hr. Further aliquots of diphenyl phosphoryl azide (323 μL, 1.0 mmol) and Et3N (280 μL, 2.0 mmol) were added and the mixture was stirred at room temperature overnight. H2O (20 mL) and CH2Cl2 (15 mL) were added and the aqueous and organic layers were partitioned. The aqueous layer was extracted with CH2Cl2 (2×20 mL), and the combined organic layers were dried over Na2SO4, filtered and the solvent was removed under vacuum to leave a crude residue.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 4 hr
  3. stirringthe mixture was stirred at room temperature overnight
  4. customthe aqueous and organic layers were partitioned
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-97d379b18bcd4bd7bec6fe78254c73ef
Source dataset
uspto-grants-2016_09
Patent number
US09439888B2

Linked notes

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