1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → HCID 14795765, compound

HRID 1494742Notes

Reaction equation

HRID 1494742 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH2:23][NH:24][CH2:25]2>CN(C=O)C>[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH2:23][N:24]([C:11]1[CH:12]=[C:13]3[C:8]([C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=1[F:15])[CH2:25]2

Participants

4

Reactant 2

HCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 147958674-fluoro-2,3-dihydro-1H-isoindole

Product 1

HCID 14795765HCID 14795765, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 136 mg of 1-cyclopropyl-6,7-difluoro-1,4- dihydro-4-oxoquinoline-3-carboxylic acid, 206 mg of 4-fluoroisoindoline, and 1.5 ml of anhydrous DMF was heated at 110° C. for 1.5 hours while stirring. The resulting reaction mixture was evaporated under reduced pressure to dryness. 20 ml of chloroform and 10 ml of 5% acetic acid were added to the residue thus obtained, and the mixture was stirred. The deposited crystals were collected by filtration and washed with water and then ethanol. The chloroform layer was separated, washed with water, dried over anhydrous sodium sulfate, and condensed. The residue was crystallized by the addition of hot ethanol. After cooling the mixture, the crystals were collected by filtration. These crystals, combined with the crystals obtained above, were recrystallized from a mixed solvent of chloroform, methanol, and ethanol to obtain 85 mg of the target compound.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated under reduced pressure to dryness
  3. addition20 ml of chloroform and 10 ml of 5% acetic acid were added to the residue
  4. customthus obtained
  5. stirringthe mixture was stirred
  6. filtrationThe deposited crystals were collected by filtration
  7. washwashed with water
  8. customThe chloroform layer was separated
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate, and condensed
  11. customThe residue was crystallized by the addition of hot ethanol
  12. temperatureAfter cooling the mixture
  13. filtrationthe crystals were collected by filtration
  14. customobtained above,
  15. customwere recrystallized from a mixed solvent of chloroform, methanol, and ethanol

Sources & evidence

ORD record
ord-9441088be47c496cb8ff5cb2a5772942
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

Loading…