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Diethyl Malonate → 1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

HRID 483290
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HRID 483290 반응식
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.[Na].[C:15](Cl)(=O)C(Cl)=O.[C:21]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:22][C:23](OCC)=O.[Mg].[F:33][C:34]1[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[CH:44][C:35]=1[C:36]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:37].C(OC(OCC)OCC)C.C(OC(=O)C)(=O)C.[CH:68]1([NH2:71])[CH2:70][CH2:69]1>>[CH:68]1([N:71]2[C:2]3[C:3](=[CH:7][C:8]([F:13])=[C:9]([F:12])[C:10]=3[F:11])[C:4](=[O:6])[C:22]([C:21]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23]2)[CH2:70][CH2:69]1.[F:33][C:34]1[C:47]([F:48])=[C:46]([F:49])[C:45]([F:50])=[CH:44][C:35]=1[C:36]([C:38](=[CH:15][NH:71][CH:68]1[CH2:70][CH2:69]1)[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:37]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 9

HCID 7761Diethyl MalonateHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 2975492,3,4,5-Tetrafluorobenzoic acid2회HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate
HCID 5360545
Sodium
HCID 5462224Magnesium

생성물 2

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 178471877HCID 178471877, 화합물

실험 절차

The starting materials for the present invention are known, or if new, may be prepared from known materials by known means. Thus, ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate is prepared as described in Belgian Pat. No. 899,399 or No. DE3318145. Alternatively, it may be prepared by a series of reactions starting from 2,3,4,5-tetrafluorobenzoic acid. The sodium salt of 2,3,4,5-tetrafluorobenzoic acid is reacted with oxalyl chloride and the product condensed with diethyl malonate in the presence of magnesium turnings to afford after hydrolysis 2,3,4,5-tetrafluorobenzoylacetic acid, ethyl ester. This compound is, in turn, treated with triethylorthoformate and acetic anhydride, followed by cyclopropylamine to afford 2-(2,3,4,5-tetrafluorobenzoyl)-3-cyclopropylamino acrylic acid, ethyl ester, which is then ring closed to give the desired starting material. The corresponding methyl ester is prepared using dimethylmalonate in the sequence described above.

후처리

  1. customif new, may be prepared
  2. customAlternatively, it may be prepared by a series of reactions
  3. customto afford

출처 및 근거

ORD 기록
ord-3292f44d3208476cb08631810f010c12
출처 데이터셋
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04578473

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