Chloroform → ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

HRID 600875Notes

Reaction equation

HRID 600875 reaction equation
[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][N:9]2[C@@H:14]2[CH2:16][C@@H:15]2[F:17])=[C:4]([N+:24]([O-])=O)[CH:3]=1.C(Cl)(Cl)Cl>C(#N)C.[C].[Pd]>[NH2:24][C:4]1[CH:3]=[C:2]([F:1])[C:11]([O:12][CH3:13])=[C:10]2[C:5]=1[C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][N:9]2[C@@H:14]1[CH2:16][C@@H:15]1[F:17]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 67272210Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

Product 1

HCID 67271608ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (3.71 g, 10.1 mmol) was dissolved in acetonitrile (50 ml), and after adding a 5% palladium carbon catalyst (water content: 50%, 1.5 g) thereto, it was stirred at room temperature for 20 hours under a hydrogen atmosphere at atmospheric pressure. After removing the catalyst by filtering (methanol washing), the filtrate was concentrated under a reduced pressure, the residue obtained was applied to a silica gel chromatography, and 2.68 g (79%) of the title compound was obtained as a yellow amorphous substance from a chloroform:methanol=30:1 eluate.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtering (methanol washing)
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. customthe residue obtained

Sources & evidence

ORD record
ord-76dca5279b8049f3972806d518cc5d54
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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