HCID 11103220, compound → HCID 502078, compound

HRID 377293Notes

Reaction equation

HRID 377293 reaction equation
C(OC([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[C:29]([O:30][CH3:31])=[C:28]4[C:23]([C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26][N:27]4[CH:32]4[CH2:34][CH2:33]4)=[CH:22][CH:21]=3)[CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1>C(O)(=O)C.[C].[Pd]>[CH:32]1([N:27]2[C:28]3[C:23](=[CH:22][CH:21]=[C:20]([C:16]4[CH:17]=[C:18]5[C:13](=[CH:14][CH:15]=4)[CH2:12][NH:11][CH2:19]5)[C:29]=3[O:30][CH3:31])[C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26]2)[CH2:33][CH2:34]1

Participants

4

Reactant 1

HCID 11103220HCID 11103220, compound

Product 1

HCID 502078HCID 502078, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In 14 ml of acetic acid and 140 mg of 5% palladium-carbon was suspended 140 mg of 7-[2-(benzyl-oxycarbonyl)isoindolin-5-yl]-1-cyclopropyl-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, and the suspension was stirred at room temperature for 2 hours under a hydrogen atomsphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Ethanol and diethyl ether were added to the resulting residue and the crystals were collected by filtration. To the crystals collected were added 0.8 ml of ethanol, 0.8 ml of a 1N aqueous sodium hydroxide solution and 0.8 ml of water to dissolve the crystals, after which carbon dioxide was bubbled into the resulting solution and the crystals were collected by filtration to obtain 74 mg of colorless 1-cyclopropyl-7-(isoindolin-5-yl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionEthanol and diethyl ether were added to the resulting residue
  4. filtrationthe crystals were collected by filtration
  5. customTo the crystals collected
  6. additionwere added 0.8 ml of ethanol, 0.8 ml of a 1N aqueous sodium hydroxide solution and 0.8 ml of water
  7. dissolutionto dissolve the crystals
  8. customafter which carbon dioxide was bubbled into the resulting solution
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-87b2aa7b89df4e44b5566933059c80ca
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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