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

HRID 344900Notes

Reaction equation

HRID 344900 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].[CH2:24]([CH:31]1[CH2:36][NH:35][CH2:34][CH2:33][NH:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CS(C)=O>[CH2:24]([CH:31]1[NH:32][CH2:33][CH2:34][N:35]([C:18]2[C:19]([F:21])=[CH:20][C:10]3[C:11]([CH:17]=2)=[N:12][C:13]2[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7](=[O:23])[C:8]=2[CH:9]=3)[CH2:36]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5590332-BenzylpiperazineHCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54492054(RS)-8-(3-benzyl-1-piperazinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 82.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.3 g) and (RS)-2-benzylpiperazine (1.3 g) in dimethyl sulphoxide (25 cc) is heated to approximately 90° C. with stirring for 1 hour 45 minutes. After cooling to a temperature in the region of 20° C., the reaction mixture is treated with water (100 cc) and extracted with trichloromethane (3×30 cc). The combined organic extracts are washed with water (3×30 cc), dried over magnesium sulphate, filtered and concentrated to dryness at approximately 50° C. under reduced pressure (20 kPa). After 1 recrystallization in a mixture of dimethylformamide (4 cc) and ethanol (1 cc), (RS)-8-(3-benzyl-1-piperazinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.6 g) is obtained in the form of a yellow solid, m.p. 190° C.

Workup

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. extractionextracted with trichloromethane (3×30 cc)
  3. washThe combined organic extracts are washed with water (3×30 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness at approximately 50° C. under reduced pressure (20 kPa)
  7. customAfter 1 recrystallization
  8. additionin a mixture of dimethylformamide (4 cc) and ethanol (1 cc)

Sources & evidence

ORD record
ord-a4445115b8f54030a617eb24518ac681
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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