HCID 23284678, compound → HCID 23284677, compound

HRID 369297Notes

Reaction equation

HRID 369297 reaction equation
[N:1]([C:4]1[C:13]([Cl:14])=[C:12]2[C:7]([C:8](=[O:36])[C:9]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:10][N:11]2[C:15]2[CH:20]=[C:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:18]([F:29])=[CH:17][C:16]=2[F:30])=[C:6]([CH3:37])[C:5]=1[F:38])=[N+]=[N-].[H][H]>CO.[OH-].[Pd+2].[OH-].[C]>[NH2:1][C:4]1[C:13]([Cl:14])=[C:12]2[C:7]([C:8](=[O:36])[C:9]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:10][N:11]2[C:15]2[CH:20]=[C:19]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:18]([F:29])=[CH:17][C:16]=2[F:30])=[C:6]([CH3:37])[C:5]=1[F:38]

Participants

5

Reactant 2

HCID 23284678HCID 23284678, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23284677HCID 23284677, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide-carbon (180 mg) was added to a solution of ethyl 7-azido-1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-8-chloro-6-fluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.75 g) in methanol (9 ml), and the mixture was stirred at room temperature for 2.5 hours in a hydrogen atmosphere. The catalyst was removed by filtration through a membrane filter, and the solvent in the filtrate was distilled off under reduced pressure. 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. customThe catalyst was removed by filtration through a membrane
  2. filtrationfilter
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. washelution with chloroform

Sources & evidence

ORD record
ord-c60beaf8505b45f6b8146ed5c215ae01
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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