Triethylamine → 7-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbOxylic acid, ethyl ester

HRID 1654514노트

반응식

HRID 1654514 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[N:27]=[C:26]2[C:21]([C:22](=[O:39])[C:23]([C:36]([OH:38])=[O:37])=[CH:24][N:25]2[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])=[CH:20][C:19]=1[F:40].[CH2:41](N(CC)CC)[CH3:42].C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C.CCCCCC.CO>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:12][CH2:13][N:14]([C:18]3[N:27]=[C:26]4[C:21]([C:22](=[O:39])[C:23]([C:36]([O:38][CH2:41][CH3:42])=[O:37])=[CH:24][N:25]4[C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=4[F:35])=[CH:20][C:19]=3[F:40])[CH2:15][CH2:16]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 15282171tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamateHCID 21226206Ethyl acetate hexane

생성물 1

HCID 152821727-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbOxylic acid, ethyl ester수율 86%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21879739Ethyl acetate hexane methanol용매

실험 절차

A solution of 1-tert-butoxycarbonylamino-6-azaspiro[2.5]octane (250 mg, 1.11 mmol), the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (382 mg, 1.00 mmol) and triethylamine (0.78 ml, 5.55 mmol) in acetonitrile (15 ml) was heated at reflux overnight. Solvent was removed in vacuo and the residue was chromatographed on silica gel (eluents: 50% ethyl acetate/hexane, then 5:5:1 ethyl acetate/hexane/methanol) to afford the title product as an off-white solid (494 mg, 0.86 mmol, yield 86%).

후처리

  1. temperatureat reflux overnight
  2. customSolvent was removed in vacuo
  3. customthe residue was chromatographed on silica gel (eluents

출처 및 근거

ORD 기록
ord-a71b47f913864fcda7384169f9095f30
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05407943

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