Water → (RS)-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344915Notes

Reaction equation

HRID 344915 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]1[CH2:34][NH:33][CH2:32][CH2:31][NH:30]1.C(=O)([O-])[O-].[Na+].[Na+].O>CS(C)=O.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:33]4[CH2:32][CH2:31][NH:30][CH:29]([C:25]5[O:24][CH:28]=[CH:27][CH:26]=5)[CH2:34]4)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 167407772-(Furan-2-yl)piperazine

Product 1

HCID 53959778(RS)-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 95.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (0.96 g), (RS)-2-(2-furyl)piperazine (0.6 g) and sodium carbonate (0.38 g) in dimethyl sulphoxide (20 cc) is heated to approximately 95° C. for 5 hours and a half. After cooling to approximately 20° C., the mixture is poured into water (50 cc) at a temperature in the region of 5° C. and extracted with dichloromethane (3×100 cc). The combined organic extracts are washed with water (3×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 kPa) at approximately 40° C. The residue obtained is taken up with ethanol (20 cc), drained and washed with ethanol (2×20 cc) and ethyl ether (3×30 cc). (RS)-3-Ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.3 g) is obtained in the form of a yellow solid, m.p. 198°-200° C., which is used without further purification for the subsequent steps.

Workup

  1. temperatureAfter cooling to approximately 20° C.
  2. extractionextracted with dichloromethane (3×100 cc)
  3. washThe combined organic extracts are washed with water (3×50 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (20 kPa) at approximately 40° C
  7. customThe residue obtained
  8. washwashed with ethanol (2×20 cc) and ethyl ether (3×30 cc)

Sources & evidence

ORD record
ord-e2719abbcea246f294066d45c966d30b
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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