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N-Methylpiperidine → 7-[3-(r)-(1-Aminocyclopropyl)pyrrolidin-1-yl]-1-[2-(s)-fluoro-1-(r)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 600909
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인쇄 미리보기

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HRID 600909 반응식
F[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[C:4]([OH:21])[CH:3]=1.C(OC([NH:29][C:30]1([C@@H:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH2:32][CH2:31]1)=O)(C)(C)C.CN1CCCCC1>CS(C)=O>[NH2:29][C:30]1([C@@H:33]2[CH2:37][CH2:36][N:35]([C:2]3[C:11]([CH3:12])=[C:10]4[C:5]([C:6](=[O:20])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]4[C@@H:13]4[CH2:15][C@@H:14]4[F:16])=[C:4]([OH:21])[CH:3]=3)[CH2:34]2)[CH2:32][CH2:31]1
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참가 물질

5

반응물 3

HCID 12291N-MethylpiperidineHCID 11117758(R)-t-Butyl (1-(pyrrolidin-3-yl)cyclopropyl)carbamateHCID 672715427-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-Carboxylic Acid

생성물 1

HCID 672719247-[3-(r)-(1-Aminocyclopropyl)pyrrolidin-1-yl]-1-[2-(s)-fluoro-1-(r)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
80 °C

실험 절차

A mixture of 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (205 mg, 0.694 mmol), 3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]pyrrolidine (314 mg, 1.388 mmol), N-methyl piperidine (0.243 ml, 1.388 mmol), and dimethyl sulfoxide (1.5 ml) was stirred for 66 hours while heating in an oil bath at 80° C. under a nitrogen-replaced atmosphere. After evaporating the solvent, the residue was partitioned in chloroform (50 ml) and 10% aqueous citric acid solution (30 ml), and after separating the organic layer, the aqueous layer was further subject to extraction into chloroform (30 ml). The combined organic layer was then dried over anhydrous sodium sulfate, and after removing the drying agent by filtration, the solvent was evaporated under a reduced pressure to thereby obtain a crude 7-{3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]pyrrolidin-1-yl}-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

후처리

  1. customAfter evaporating the solvent
  2. customthe residue was partitioned in chloroform (50 ml)
  3. custom10% aqueous citric acid solution (30 ml), and after separating the organic layer
  4. extractionthe aqueous layer was further subject to extraction into chloroform (30 ml)
  5. dry with materialThe combined organic layer was then dried over anhydrous sodium sulfate
  6. customafter removing the drying agent
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

출처 및 근거

ORD 기록
ord-706bfe948b1e4e01ab4381348b6a46f0
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902226B2

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