3-Pyrrolidinemethanamine → 7-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 542473노트

반응식

HRID 542473 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1>C(#N)C.C(OCC)C>[NH2:27][CH2:26][CH:23]1[CH2:24][CH2:25][N:21]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4][N:3]3[CH2:1][CH3:2])=[C:8]([F:16])[C:9]=2[F:15])[CH2:22]1

참가 물질

5

반응물 2

HCID 50687753-PyrrolidinemethanamineHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

생성물 1

HCID 138510207-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid수율 82%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

반응 조건

온도
45 °C

실험 절차

To 1.0 g (3.5 mmol) of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 20 ml of acetonitrile was added 1.05 g (6.9 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.35 g (3.5 mmol) of 3-pyrrolidinemethanamine and the mixture was stirred at 45° C. for 18 hours, then refluxed one hour. The mixture was cooled, diluted with 50 ml of diethyl ether, and filtered. The solids were washed with ethanol and then diethyl ether to give 1.04 g (82%) of the title compound, mp>170° C. (decomposition).

후처리

  1. temperaturerefluxed one hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe solids were washed with ethanol

출처 및 근거

ORD 기록
ord-161784c58b764fa5b8e92a568880dff1
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04657913

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