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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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tert-butyl N-(pyrrolidin-3-yl)carbamate → 7-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid

HRID 364054
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인쇄 미리보기

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HRID 364054 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([NH:14][CH3:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[NH:20]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]1>C(#N)C>[CH3:30][C:28]([CH3:31])([O:27][C:26]([NH:25][CH:22]1[CH2:23][CH2:24][N:20]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]3[NH:14][CH3:15])=[CH:3][C:2]=2[F:1])[CH2:21]1)=[O:32])[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 135580371-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

생성물 1

HCID 705150537-[3-[[(1,1Dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid수율 57.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To 1.00 g (3.68 mmol) of 6,7,8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid in 10 ml of acetonitrile was added 0.56 g (1.0 equivalent) of 1,8-diazobicyclo-[5,4,0]undec-7-ene and 0.68 g of 1,1-dimethylethyl 3-pyrrolidinylcarbamate. The mixture was refluxed for one hour and stirred at room temperature overnight. The solids were filtered and washed with ether to give 0.92 g of 7-[3-[[(1,1dimethylethoxy)carbonyl]amino]-1-pyrro-lidinyl]-6,8-difluoro-1,4-dihydro-1-(methylamino)-4-oxo-3quinolinecarboxylic acid. A portion of this material (0.38 g) was treated with 10 ml of trifluoroacetic acid for 2 hours and was concentrated. The residue was taken up in aqueous sodium hydroxide to pH 12.5 and then treated with hydrochloric acid to pH 7.0. The solids were filtered to give 0.24 g of 7-(3-amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, mp 210°-211° C.

후처리

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe solids were filtered
  3. washwashed with ether

출처 및 근거

ORD 기록
ord-597dd3106fde4a2189a52777bbd0c6a2
출처 데이터셋
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04604401

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