Methanesulfonic Acid → HCID 14853344, compound

HRID 1084402Notes

Reaction equation

HRID 1084402 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:30])[C:8]2[CH:9]=[C:10]3[CH:21]=[C:20]([F:22])[C:19]([N:23]4[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]4)=[CH:18][C:11]3=[N:12][C:13]=2[N:14]([O:16][CH3:17])[CH:15]=1)=[O:5])C.CS(O)(=O)=O>C(O)C.O.[OH-].[K+].C(OC(C)C)(C)C>[F:22][C:20]1[C:19]([N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)=[CH:18][C:11]2=[N:12][C:13]3[N:14]([O:16][CH3:17])[CH:15]=[C:6]([C:4]([OH:5])=[O:3])[C:7](=[O:30])[C:8]=3[CH:9]=[C:10]2[CH:21]=1

Participants

7

Reactant 2

HCID 6395Methanesulfonic AcidHCID 14853347HCID 14853347, compound

Product 1

HCID 14853344HCID 14853344, compoundYield 32.8%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolventHCID 14797Potassium HydroxideSolvent

Procedure

A suspension of 0.98 g of 3-ethoxycarbonyl-7-fluoro-1-methoxy-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine in 15 cm3 of ethanol, 9 cm3 of water and 6 cm3 of 2 N aqueous potassium hydroxide solution is stirred at a temperature close to 20° C. for 1 hour. 6 cm3 of 2 N methanesulphonic acid are added to the solution obtained and the mixture is extracted with 3 times 10 cm3 of trichloromethane. The combined organic extracts are washed with 3 times 5 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 kPa) at about 50° C. The dry extract obtained is taken up in 5 cm3 of diisopropyl ether, drained and washed with twice 2 cm3 of the same solvent. After recrystallizing once from 30 cm3 of dimethylformamide containing 30% of ethanol, 0.3 g of 7-fluoro-1-methoxy-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a brown solid melting at 270° C.

Workup

  1. customclose to 20° C. for 1 hour
  2. customobtained
  3. extractionthe mixture is extracted with 3 times 10 cm3 of trichloromethane
  4. washThe combined organic extracts are washed with 3 times 5 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (20 kPa) at about 50° C
  8. extractionThe dry extract
  9. customobtained
  10. washwashed with twice 2 cm3 of the same solvent
  11. customAfter recrystallizing once from 30 cm3 of dimethylformamide containing 30% of ethanol

Sources & evidence

ORD record
ord-c00c1342691840dfabdba9719bd11c39
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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