Water → HCID 23284678, compound

HRID 369296Notes

Reaction equation

HRID 369296 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([NH:12][C:13]1[C:14]([F:40])=[CH:15][C:16]([F:39])=[C:17]([N:19]2[C:28]3[C:23](=[C:24]([CH3:32])[C:25]([F:31])=[C:26](F)[C:27]=3[Cl:29])[C:22](=[O:33])[C:21]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:20]2)[CH:18]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O.C(OCC)(=O)C>CN(C)C=O>[N:1]([C:26]1[C:27]([Cl:29])=[C:28]2[C:23]([C:22](=[O:33])[C:21]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:20][N:19]2[C:17]2[CH:18]=[C:13]([NH:12][C:10]([O:9][C:5]([CH3:7])([CH3:8])[CH3:6])=[O:11])[C:14]([F:40])=[CH:15][C:16]=2[F:39])=[C:24]([CH3:32])[C:25]=1[F:31])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 23284765HCID 23284765, compound

Product 1

HCID 23284678HCID 23284678, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium azide (500 mg) was added to a solution of ethyl 1-(5-tert-butoxycarbonylamino-2 4-difluorophenyl)-8-chloro-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (2 g) in N,N-dimethylformamide (20 ml), and the mixture was heated and stirred at 70° C. for 4 hours. After water and ethyl acetate were added to the reaction mixture, and an organic layer was collected and dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was subjected to column chromatography on silica gel to conduct elution with chloroform, thereby obtaining the title compound (1.75 g) as a brown oil.

Workup

  1. temperaturethe mixture was heated
  2. customan organic layer was collected
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washelution with chloroform

Sources & evidence

ORD record
ord-dd5ec56d344c44ddbf91e2da76742adb
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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