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 1654514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654514
[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]

Komponenten

7

Edukt 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

Produkt 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 esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 21879739Ethyl acetate hexane methanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a71b47f913864fcda7384169f9095f30
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407943

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