Ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate → Ethyl 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate

HRID 561181Notes

Reaction equation

HRID 561181 reaction equation
C([NH:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[C:15]2[C:10]=1[C:11](=[O:32])[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13][N:14]2[CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)C1C=CC=CC=1>CC(O)=O.[Pd]>[NH2:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[C:15]2[C:10]=1[C:11](=[O:32])[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13][N:14]2[CH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 59003006Ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate

Product 1

HCID 59002859Ethyl 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylateYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate (112 mg, 0.252 mmol) in AcOH (5 mL), was added 10% Pd—C (11.2 mg), the whole mixture was stirred at room temperature for 4 h under H2 atmosphere (1 atm). After insoluble materials were filtered off, the filtrate was concentrated in vacuo. Flash chromatography of the residue (EtOAc) gave ethyl 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(tetrahydropyran-4-yl)-3-quinolinecarboxylate (76.5 mg, 86%) as pale yellow powder.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3ce480d63c984a3db0a71db35ff5fdf6
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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