1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-3-quinolinecarboxylic acid

HRID 1589576노트

반응식

HRID 1589576 반응식
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].Cl.Cl.[CH3:22][N:23]1[CH:28]2[CH2:29][CH2:30][CH:24]1[CH2:25][NH:26][CH2:27]2>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([CH:25]3[NH:26][CH2:27][CH:28]4[N:23]([CH3:22])[CH:24]3[CH2:30][CH2:29]4)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

참가 물질

4

반응물 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

생성물 1

HCID 135658271-Ethyl-6,8-difluoro-1,4-dihydro-7-(8-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-3-quinolinecarboxylic acid수율 44.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1.40 g (5.0 mmole) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 2.0 g (8 mmole) of 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride [P. A. Sturm et al., J. Med. Chem., 17, 481 (1974)], 2.0 ml (13.3 mmole) of 1,8-diazobicyclo[5.4.0]undec-7-ene, and 75 ml of acetonitrile was heated under reflux for 1.5 hr and then stirred at room temperature for 22 hours. The reaction mixture was evaporated to dryness and the residue was recrystallized from 2-propanol to give 0.84 g of the title compound, mp 184°-187° C.

후처리

  1. temperatureunder reflux for 1.5 hr
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was recrystallized from 2-propanol

출처 및 근거

ORD 기록
ord-38223ad0e8c44edbb068c3a662af735e
출처 데이터셋
uspto-grants-1986_02
특허 번호
US04571396

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