Water → Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 232496Notes

Reaction equation

HRID 232496 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:44])=[C:22](OS(C3C(C(C)C)=CC(C(C)C)=CC=3C(C)C)(=O)=O)[N:23]=2)[C:18](=[O:45])[C:17]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:16]1.C(OCC)(=O)C.O>C(Cl)Cl.C(OCC)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N:15]1[C:24]2[C:19](=[CH:20][C:21]([F:44])=[C:22]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[N:23]=2)[C:18](=[O:45])[C:17]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 8857Ethyl AcetateHCID 13849335Ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(2,4,6-triisopropylbenzenesulfonyloxy)-1,8-naphthyridine-3-carboxylate

Product 1

HCID 13849334Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 91.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In 4 ml of methylene chloride was dissolved 270 mg of anhydrous piperazine, and 400 mg of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(2,4,6-triisopropylbenzenesulfonyloxy)-1,8-naphthyridine-3-carboxylate was added to the resulting solution, after which the resulting mixture was subjected to reaction with ice-cooling for 1 hour. To the reaction mixture were added 20 ml of ethyl acetate and 10 ml of water, and the organic layer was separated, washed successively with 10 ml of saturated aqueous sodium hydrogencarbonate solution and 10 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 5 ml of diethyl ether, after which crystals were collected by filtration to obtain 250 mg (yield 91.2%) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate having a melting point of 208°-211° C.

Workup

  1. additionwas added to the resulting solution
  2. customafter which the resulting mixture was subjected to reaction with ice-
  3. temperaturecooling for 1 hour
  4. customthe organic layer was separated
  5. washwashed successively with 10 ml of saturated aqueous sodium hydrogencarbonate solution and 10 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customto the crystalline material thus obtained
  9. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-cfe286a492bb46feab1629d1f0a96f97
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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