Triethylamine → Balofloxacin

HRID 729071노트

반응식

HRID 729071 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:24][NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1.C(N(CC)CC)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([N:28]4[CH2:29][CH2:30][CH2:31][CH:26]([NH:25][CH3:24])[CH2:27]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 248201743-(Methylamino)piperidine Dihydrochloride

생성물 1

HCID 65958Balofloxacin수율 32.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (2.95 g), 3-methylaminopiperidine dihydrochloride (6.69 g) and triethylamine (10 g) in acetonitrile (50 ml) was refluxed with stirring for 12 hours. The reaction mixture was concentrated in vacuum, and the residue was extracted with chloroform. The extract was washed with a saturated NaCl solution and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol:ammoniumhydroxide=15:5:1) to give 1.28 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylaminopiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid, which was recrystallized from acetonitrile-water, colorless needles. m.p. 134°-135° C.

후처리

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. extractionthe residue was extracted with chloroform
  4. washThe extract was washed with a saturated NaCl solution
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol:ammoniumhydroxide=15:5:1)

출처 및 근거

ORD 기록
ord-dd25ea9811824df3a8893ee00e15b20c
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051509

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