Water → HCID 14853344, compound

HRID 1084388Notes

Reaction equation

HRID 1084388 reaction equation
[F:1][C:2]1[C:21](F)=[CH:20][C:5]2=[N:6][C:7]3[N:8]([O:18][CH3:19])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.O.CS(O)(=O)=O.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CS(C)=O>[F:1][C:2]1[C:21]([N:33]2[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]2)=[CH:20][C:5]2=[N:6][C:7]3[N:8]([O:18][CH3:19])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 531671-MethylpiperazineHCID 148533437,8-Difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 14853344HCID 14853344, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 0.93 g of 7,8-difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid in 0.6 g of 1-methylpiperazine and 20 cm3 of dimethyl sulphoxide is heated at a temperature close to 80° C. for 5 minutes. After cooling to about 20° C., the reaction mixture is poured into 30 cm3 of water, 1.5 cm3 of 2 N methanesulphonic acid are added and the product is drained and washed with 3 times 5 cm3 of water. After recrystallizing from 30 cm3 of dimethylformamide containing 30% of ethanol, 0.55 g of 7-fluoro-1-methoxy-8-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a brown solid melting at 270° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 80° C. for 5 minutes
  3. additionare added
  4. washwashed with 3 times 5 cm3 of water
  5. customAfter recrystallizing from 30 cm3 of dimethylformamide containing 30% of ethanol

Sources & evidence

ORD record
ord-543a4728ffea42cc9ede295e7af7501d
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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