3-Methylpyridine → 7-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580571

반응식

HRID 580571 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].N1C=CC=C(C)C=1.[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][NH:30][CH2:29]1>N>[NH2:26][CH2:27][CH:28]1[CH:32]([CH3:33])[CH2:31][N:30]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:29]1

참가 물질

5

반응물 3

HCID 79703-MethylpyridineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 4583498(4-Methylpyrrolidin-3-yl)methanamine

생성물 1

HCID 139330927-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid수율 21.7%

시약·촉매·용매 1

HCID 222Ammonia용매

실험 절차

A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C.

후처리

  1. temperaturewas refluxed for 8.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added dichloromethane-ether (1:3, 37 ml)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with ethanol-ether (1:3)
  6. customrecrystallized from ethanol
  7. customfurther recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1)

출처 및 근거

ORD 기록
ord-f139f10be90c4dafa9e9508b53e7e7e3
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04753953

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