Water → HCID 20063304, compound

HRID 1084405Notes

Reaction equation

HRID 1084405 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.O>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 20063304HCID 20063304, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 2 g of 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine in 30 cm3 of dimethyl sulphoxide and 5 g of piperazine is heated at a temperature close to 100° C., with stirring, for 2 hours. The solution obtained at about 100° C. is poured, with stirring, into a mixture of 150 cm3 of water and 50 g of ice. The solution is extracted with 3 times 40 cm3 of trichloromethane. The combined organic phases are extracted with twice 50 cm3 of 0.1 N methanesulphonic acid. 10 g of potassium carbonate are added to the combined aqueous phases. The mixture is extracted with 3 times 40 cm3 of trichloromethane. The combined organic extracts are washed with twice 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The residue obtained is recrystallized from 25 cm3 of ethanol. 0.8 g of 3-ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine is obtained in the form of a yellow solid melting at 221° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 100° C.
  3. customThe solution obtained at about 100° C.
  4. additionis poured
  5. extractionThe solution is extracted with 3 times 40 cm3 of trichloromethane
  6. extractionThe combined organic phases are extracted with twice 50 cm3 of 0.1 N methanesulphonic acid
  7. addition10 g of potassium carbonate are added to the combined aqueous phases
  8. extractionThe mixture is extracted with 3 times 40 cm3 of trichloromethane
  9. washThe combined organic extracts are washed with twice 50 cm3 of water
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure (20 kPa) at about 50° C
  13. customThe residue obtained
  14. customis recrystallized from 25 cm3 of ethanol

Sources & evidence

ORD record
ord-2644ffbf08e34834bf85f15b2903c3a5
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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