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

HRID 344882Notes

Reaction equation

HRID 344882 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].[C:25]1([CH:31]2[CH2:36][NH:35][CH2:34][CH2:33][NH:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH: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:35]4[CH2:34][CH2:33][NH:32][CH:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:36]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 2506732-PhenylpiperazineHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 53821323(RS)-3-ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridineYield 78.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.8 g) and (RS)-2-phenylpiperazine (3.2 g) in dimethyl sulphoxide (30 cc) is heated to a temperature in the region of 100° C. with stirring for 1 hour and a half. The solution obtained, at approximately 100° C., is poured with stirring into a mixture of water (150 cc) and ice (50 g). The suspension obtained is extracted at approximately 20° C. with trichloromethane (3×40 cc). The combined organic extracts are washed with water (2×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 kPa) at approximately 50° C. The solid obtained is recrystallized in a mixture of dimethylformamide (40 cc) and ethanol (40 cc). (RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-(3-phenyl-1-piperazinyl)-1,4-dihydrobenzo[b][1,8]naphthyridine (2 g) is obtained in the form of a yellow solid, m.p. 216° C.

Workup

  1. customThe solution obtained, at approximately 100° C.
  2. additionis poured
  3. customThe suspension obtained
  4. extractionis extracted at approximately 20° C. with trichloromethane (3×40 cc)
  5. washThe combined organic extracts are washed with water (2×50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (20 kPa) at approximately 50° C
  9. customThe solid obtained
  10. customis recrystallized in a mixture of dimethylformamide (40 cc) and ethanol (40 cc)

Sources & evidence

ORD record
ord-be347fb2485e43659fd67935931e71fb
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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