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 727939ノート

反応式

HRID 727939 の反応式
[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]

参加物

5

反応物 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

生成物 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 acid収率 72.5%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4409d5e908d144e9b6ef0d93f3886dc4
出典データセット
uspto-grants-1991_09
特許番号
US05045549

反応ノート

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