1-Methylpiperazine → HCID 14853346, compound

HRID 1073623Notes

Reaction equation

HRID 1073623 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CS(C)=O.O.C(OC(C)C)(C)C>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:30]5[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 531671-MethylpiperazineHCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 14853346HCID 14853346, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A suspension of 1.2 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 1.4 g of 1-methylpiperazine and 20 cm3 of dimethyl sulphoxide is heated at a temperature close to 95° C. for 45 minutes. After cooling to a temperature close to 20° C., the reaction mixture is diluted with 100 cm3 of water and extracted with 3 times 30 cm3 of trichloromethane. The combined organic extracts are washed with 3 times 30 cm3 of water, dried over magnesium sulphate, filtered and concentrated under reduced pressure (20 kPa) at a temperature close to 50° C. The solid obtained is taken up in 20 cm3 of diisopropyl ether, drained, washed with 10 cm3 of the same solvent and recrystallized from 150 cm3 of ethyl acetate. 1.1 g of 1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-8 -(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a yellow solid melting at 223° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 95° C. for 45 minutes
  3. temperatureAfter cooling to a temperature
  4. customclose to 20° C.
  5. extractionextracted with 3 times 30 cm3 of trichloromethane
  6. washThe combined organic extracts are washed with 3 times 30 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure (20 kPa) at a temperature
  10. customclose to 50° C
  11. customThe solid obtained
  12. washwashed with 10 cm3 of the same solvent
  13. customrecrystallized from 150 cm3 of ethyl acetate

Sources & evidence

ORD record
ord-8aa4db8a1023491d8f3f6411d3777fc0
Source dataset
uspto-grants-1990_11
Patent number
US04970213

Reaction notes

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