HCID 59002855, compound → HCID 59002956, compound

HRID 561171Notes

Reaction equation

HRID 561171 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:34])[C:12]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:13][N:14]2[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C1C=CC=CC=1>CCO.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:34])[C:12]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:13][N:14]2[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 1

HCID 59002855HCID 59002855, compound

Product 1

HCID 59002956HCID 59002956, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a suspension of ethyl 5-benzylamino-6,7-difluoro-1,4-dihydro-4-oxo-1-(2-phenylethyl)-3-quinolinecarboxylate (700 mg, 1.51 mmol) in a mixture of EtOH (2 mL) and AcOH (2 mL), was added 10% Pd—C (70.0 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. To a solution of the residue in AcOH (2 mL), a suspension of 10% Pd—C (70 mg) in AcOH (2 mL) was added, the whole mixture was stirred at room temperature for 4 h under H2 atmosphere (1 atm). After insoluble materials were filtered off and washed with DMF, the combined filtrate and washing was concentrated in vacuo. Trituration of the residue with EtOH gave ethyl 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(2-phenylethyl)-3-quinolinecarboxylate (499 mg, 89%) as pale brown powder.

Workup

  1. filtrationAfter insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo a solution of the residue in AcOH (2 mL), a suspension of 10% Pd—C (70 mg) in AcOH (2 mL)
  4. additionwas added
  5. stirringthe whole mixture was stirred at room temperature for 4 h under H2 atmosphere (1 atm)
  6. filtrationAfter insoluble materials were filtered off
  7. washwashed with DMF
  8. washthe combined filtrate and washing
  9. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7c3bc00da01349f8b2ac7afddd4273c3
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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