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Potassium Carbonate → i-Propyl 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-amino-3',3'-dimethyl-piperidin-1-yl)-4-oxo-quinoline-3-carboxylate

HRID 11303
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HRID 11303 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH:22]C(OC(C)(C)C)=O)[C:18]([CH3:31])([CH3:30])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:33])[C:6]([C:34]([OH:36])=[O:35])=[CH:5]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].I[CH2:44][CH2:45][CH3:46]>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH2:22])[C:18]([CH3:30])([CH3:31])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:33])[C:6]([C:34]([O:36][CH:45]([CH3:46])[CH3:44])=[O:35])=[CH:5]2)[CH2:2][CH2:3]1
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참가 물질

4

반응물 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 103007861-Cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-t-butoxycarbonylamino-3',3'-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

생성물 1

HCID 86760219i-Propyl 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-amino-3',3'-dimethyl-piperidin-1-yl)-4-oxo-quinoline-3-carboxylate수율 45%

반응 조건

온도
70 °C

실험 절차

In a dry dimethylformaide (15 ml) was taken a mixture of 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-t-butoxycarbonylamino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid (1 g, 1.98 mmole), K2CO3 (0.275 g, 1.98 mmole) was stirred at 70° C. for 7 hr. Added 1-iodopropane (0.5 g, 2.98 mmole) to reaction mixture and stirred at the same temperature for 16 hr. Solvent was concentrated up to dryness and (15 ml) water was added to it and extracted with chloroform (25 ml×2). Organic layer was separated, dried, concentrated, Which was hydrolysied with trifluoroacetic acid in methylene dichloride and purified on silica column to furnish titled product. Yield 45%, m.p 140–42° C., C24H32FN3O4, m/z 446 (M+1).

후처리

  1. stirringstirred at the same temperature for 16 hr
  2. concentrationSolvent was concentrated up to dryness and (15 ml) water
  3. additionwas added to it
  4. extractionextracted with chloroform (25 ml×2)
  5. customOrganic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. custompurified on silica column

출처 및 근거

ORD 기록
ord-a1b74487e4a6436087218ffd783f010b
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098219B2

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