6-Fluoro-1-(2,4-difluorophenyl)1,4-dihydro4-oxo-7-(5-benyl-2,5-diazabicyclo(2.2.1)-hept-2-yl)-quinoline-3-carboxylic acid → 7-(2,5-Diazabicyclo(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

HRID 727939Notes

Reaction equation

HRID 727939 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH:16]3[CH2:18][CH:13]1[CH2:14][N:15]3CC1C=CC=CC=1)[N:8]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33])[CH:7]=[C:6]([C:34]([OH:36])=[O:35])[C:5]2=[O:37]>C(O)C.Cl.[Pd]>[CH:13]12[CH2:18][CH:16]([NH:15][CH2:14]1)[CH2:17][N:12]2[C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:37])[C:6]([C:34]([OH:36])=[O:35])=[CH:7][N:8]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 1

HCID 140148296-Fluoro-1-(2,4-difluorophenyl)1,4-dihydro4-oxo-7-(5-benyl-2,5-diazabicyclo(2.2.1)-hept-2-yl)-quinoline-3-carboxylic acid

Product 1

HCID 140148307-(2,5-Diazabicyclo(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidYield 72.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2.57 g (5 08 m Mol) of 6-fluoro-1-(2,4-difluoro-phenyl)-1,4-dihydro-4-oxo-7-(5-benzyl-2,5-diazabicyclo(2.2.1)-hept-2-yl)quinoline-3-carboxylic acid was dissolved in 170 ml of absolute ethanol containing 18 g of HCl and to the solution was added 2.1 g 10% Pd/c and the resultant hydrogenated at 15 psi and 60° C. for 2 hrs. After filtration of the catalyst the volatiles were removed under reduced pressure. The resulting residue was taken up in 80 ml of water and the pH adjusted to 7. The resulting suspension was heated for 20 mins. at 60° C. After cooling the precipitated was filtered and recrystallized from DMF to give 1.53 g (69.5%) of product as a hydrate, mp 198° C.-204° C. dec.

Workup

  1. filtrationAfter filtration of the catalyst the volatiles
  2. customwere removed under reduced pressure
  3. temperatureThe resulting suspension was heated for 20 mins
  4. customat 60° C
  5. temperatureAfter cooling the precipitated
  6. filtrationwas filtered
  7. customrecrystallized from DMF

Sources & evidence

ORD record
ord-4409d5e908d144e9b6ef0d93f3886dc4
Source dataset
uspto-grants-1991_09
Patent number
US05045549

Reaction notes

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