Water → (RS)-3-Ethoxycarbonyl-7,9-difluoro-1-(2-fluoroethyl)-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344897Notes

Reaction equation

HRID 344897 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[C:8]2[CH:9]=[C:10]3[CH:22]=[C:21]([F:23])[C:20](F)=[C:19]([F:25])[C:11]3=[N:12][C:13]=2[N:14]([CH2:16][CH2:17][F:18])[CH:15]=1)=[O:5])[CH3:2].[C:27]1([CH:33]2[CH2:38][NH:37][CH2:36][CH2:35][NH:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[C:8]2[CH:9]=[C:10]3[CH:22]=[C:21]([F:23])[C:20]([N:37]4[CH2:36][CH2:35][NH:34][CH:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:38]4)=[C:19]([F:25])[C:11]3=[N:12][C:13]=2[N:14]([CH2:16][CH2:17][F:18])[CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2506732-PhenylpiperazineHCID 544541923-Ethoxycarbonyl-1-(2-fluoroethyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54321683(RS)-3-Ethoxycarbonyl-7,9-difluoro-1-(2-fluoroethyl)-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

(RS)-3-Ethoxycarbonyl-7,9-difluoro-1-(2-fluoroethyl)-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the following conditions: a suspension of 3-ethoxycarbonyl-1-(2-fluoroethyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2.8 g), (RS)-2-phenylpiperazine (1.7 g) and sodium carbonate (1.1 g) in dimethyl sulphoxide (40 cc) is heated with stirring to a temperature in the region of 100° C. for 2 hours. After cooling to approximately 20° C., the reaction mixture is poured into water (200 cc) and extracted with trichloromethane (3×100 cc). The combined organic extracts are washed with water (1×50 cc) and concentrated under reduced pressure (20 kPa) at a temperature in the region of 40° C. The oily residue is taken up with ethanol (100 cc) and concentrated again under reduced pressure under the above conditions. The solid obtained is recrystallized in ethanol (100 cc) containing dimethylformamide (20%), drained and washed with ethanol (2×20 cc). The expected product (2.4 g) is obtained in the form of a yellow solid, m.p. 208° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to approximately 20° C.
  3. extractionextracted with trichloromethane (3×100 cc)
  4. washThe combined organic extracts are washed with water (1×50 cc)
  5. concentrationconcentrated under reduced pressure (20 kPa) at a temperature in the region of 40° C
  6. concentrationconcentrated again under reduced pressure under the above conditions
  7. customThe solid obtained
  8. customis recrystallized in ethanol (100 cc)
  9. additioncontaining dimethylformamide (20%)
  10. washwashed with ethanol (2×20 cc)

Sources & evidence

ORD record
ord-6dce58c6cd3d4aa49046c9fb48a914b4
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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