Carbon Dioxide → HCID 15870850, compound

HRID 1584834Notes

Reaction equation

HRID 1584834 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)=[C:22]([N+:39]([O-])=O)[C:21]=3[F:42])[CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C(O)C.[OH-].[Na+].C(=O)=O>C(O)(=O)C.[C].[Pd].O>[NH2:39][C:22]1[C:21]([F:42])=[C:20]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[CH2:12][NH:11][CH2:19]3)[C:29]([O:30][CH3:31])=[C:28]2[C:23]=1[C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26][N:27]2[CH:32]1[CH2:33][CH2:34]1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 15870857HCID 15870857, compound

Product 1

HCID 15870850HCID 15870850, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 10 ml of acetic acid and 60 mg of 5% palladium carbon was suspended 85 mg of 7-[2-(benzyloxycarbonyl)isoindolin-5-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, and the suspension was stirred at room temperature for two hours under a hydrogen stream. The reaction mixture was filtered, and thereafter, 2 ml of 6N hydrochloric acid was added to the filtrate obtained, after which the resulting mixture was concentrated under reduced pressure. To the residue obtained were added ethanol, and the crystals formed were collected by filtration. To the crystals obtained were added 0.5 ml of ethanol, 0.5 ml of 1N aqueous sodium hydroxide solution and 0.5 ml of water to dissolve the crystals. Thereafter, a carbon dioxide gas was blown into the solution, and the crystals precipitated were collected by filtration, to obtain 55 mg of pale yellow, crystalline 5-amino-1-cyclopropyl-6-fluoro-7-(isoindolin-5-yl)-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition2 ml of 6N hydrochloric acid was added to the filtrate
  3. customobtained
  4. concentrationafter which the resulting mixture was concentrated under reduced pressure
  5. customTo the residue obtained
  6. customthe crystals formed
  7. filtrationwere collected by filtration
  8. customTo the crystals obtained
  9. dissolutionto dissolve the crystals
  10. customthe crystals precipitated
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c36a0959e0ba44dc9153e38c8e934445
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

Loading…