1-Methylpyrrolidine → 7-(3-Aminoazetidin-1-yl)-8-chloro-1-(3,5-difluoro-6-methoxypyridin-2-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368433Notes

Reaction equation

HRID 368433 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:26])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([O:20][CH3:21])[N:13]=1)[CH:9]=[C:8]([C:22]([OH:24])=[O:23])[C:7]2=[O:25].Cl.Cl.[NH2:30][CH:31]1[CH2:34][NH:33][CH2:32]1.CN1CCCC1>C(#N)C>[NH2:30][CH:31]1[CH2:34][N:33]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:25])[C:8]([C:22]([OH:24])=[O:23])=[CH:9][N:10]3[C:12]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([O:20][CH3:21])[N:13]=3)=[CH:5][C:4]=2[F:26])[CH2:32]1

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212448-Chloro-1-(3,5-difluoro-6-methoxypyridin-2-yl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 221212857-(3-Aminoazetidin-1-yl)-8-chloro-1-(3,5-difluoro-6-methoxypyridin-2-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 33.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 500 mg of acetonitrile were added 75 mg of 8-chloro-1-(3,5-difluoro-6-methoxypyridine-2-yl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 65 mg of 3-aminoazetidine dihydrochloride, and 150 mg of N-methylpyrrolidine, and the mixture was heated under reflux for 1 hour. The precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 28 mg of the title compound as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-e2aedd8822d84c9bb29685cdd730d59a
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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