Dimethylformamide → HCID 14846354, compound

HRID 465384Notes

Reaction equation

HRID 465384 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]([CH:13]1[CH2:15][CH2:14]1)[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1.CN(C=O)C.[H-].[Na+]>C(O)(=O)C>[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][C:11]2[CH:10]=[C:9]3[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]3[CH:13]3[CH2:15][CH2:14]3)=[CH:3][C:2]=2[F:1])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 14846354HCID 14846354, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 530 mg of 6,7-difluoro-1-cyclopropyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 690 mg of N-methyl-4-piperidinol and 8 ml of DMF was added 320 mg of 60% sodium hydride while the former was stirred under ice cooling. After the resultant mixture was stirred for 10 minutes at room temperature, 480 mg of acetic acid was added. DMF was distilled off under reduced pressure. To the residue was added 15 ml of n-hexane. The resultant mixture was thoroughly shaken and mixed. The supernatant was discarded. To the resultant precipitate was added 8 ml of ethanol, followed by stirring. A precipitate thus precipitated was collected by filtration, whereby 578 mg of the title compound was obtained.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. additionTo the residue was added 15 ml of n-hexane
  3. stirringThe resultant mixture was thoroughly shaken
  4. additionmixed
  5. additionTo the resultant precipitate was added 8 ml of ethanol
  6. stirringby stirring
  7. customA precipitate thus precipitated
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-50e1a3dfdb904c6c8be673951f6d1590
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

Loading…