Dabco → 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid

HRID 1382215노트

반응식

HRID 1382215 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[OH:20][CH:21]1[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23][CH:22]1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.N12CCN(CC1)CC2>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([N:33]4[CH2:34][CH2:35][N:30]([CH:22]5[CH:21]([OH:20])[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23]5)[CH2:31][CH2:32]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

참가 물질

5

반응물 3

HCID 9237DabcoHCID 483180Fluoroquinolonic acidHCID 212744861-(6-Hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine

생성물 1

HCID 138507991-Cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid수율 10.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

2.8 g (10 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are heated at 140° in 30 ml of dimethyl sulphoxide with 2.5 g (11 mmol) of 1-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine and 2.25 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane for 4 hours, the reaction mixture is concentrated, the resulting oil is diluted with 20 ml of methanol and the pH is brought to 5 with 2N hydrochloric acid. The precipitate which has separated out is recrystallized from glycol monomethyl ether/methanol. 0.5 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid of melting point 255°-262° (with decomposition) is obtained, and is dissolved in 10 ml of 2N hydrochloric acid, with warming, to split off the protective group. After the solution has been left to stand at room temperature for 1 hour, 0.3 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[4-(1,3,4-trihydroxy-2-butyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid of melting point 262°-268° (with decomposition) has precipitated.

후처리

  1. concentrationthe reaction mixture is concentrated
  2. additionthe resulting oil is diluted with 20 ml of methanol
  3. customThe precipitate which has separated out
  4. customis recrystallized from glycol monomethyl ether/methanol

출처 및 근거

ORD 기록
ord-7a4dccf680bd4060b9ba03215390077d
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04806539

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