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 727939노트

반응식

HRID 727939 반응식
[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]

참가 물질

5

반응물 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

생성물 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 acid수율 72.5%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4409d5e908d144e9b6ef0d93f3886dc4
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05045549

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