Ethanol → HCID 15870849, compound

HRID 1584833Notes

Reaction equation

HRID 1584833 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]([Cl:30])=[C:28]4[C:23]([C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26][N:27]4[C@@H:31]4[CH2:33][C@@H:32]4[F:34])=[CH:22][C:21]=3[F:39])[CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C(O)C.[OH-].[Na+].O>C(O)(=O)C.[C].[Pd]>[Cl:30][C:29]1[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:21]([F:39])[CH:22]=[C:23]2[C:28]=1[N:27]([C@@H:31]1[CH2:33][C@@H:32]1[F:34])[CH:26]=[C:25]([C:35]([OH:37])=[O:36])[C:24]2=[O:38]

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 14798Sodium HydroxideHCID 15870856HCID 15870856, compound

Product 1

HCID 15870849HCID 15870849, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent2×

Procedure

In 25 ml of acetic acid and 50 mg of 5% palladium carbon was suspended 150 mg of 7-[2-(benzyloxycarbonyl)-isoindolin-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-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 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 0.7 ml of ethanol, 0.7 ml of 1N aqueous sodium hydroxide solution and 0.7 ml of water to dissolve the crystals, and thereafter, dilute acetic acid was added to the solution to adjust the pH to 7. The crystals precipitated were collected by filtration, to obtain 45 mg of colorless, crystalline 8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-7-(isoindolin-5-yl)-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 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-c93227492aca49e299ddaf876aa684f6
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

Loading…