Methanol → N-[3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

HRID 13837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 13837
[C:1]([N:4]([C:8]1[C:17]2[C:12](=[N:13][C:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH:16]=2)[N:11]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:10](=[O:36])[C:9]=1[Cl:37])C(=O)C)(=[O:3])[CH3:2].CO.C1COCC1>C(N(CC)CC)C>[Cl:37][C:9]1[C:10](=[O:36])[N:11]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:12]2[C:17]([C:8]=1[NH:4][C:1](=[O:3])[CH3:2])=[CH:16][C:15]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[C:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:13]=2

Komponenten

5

Edukt 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11410345N-acetyl-N-(3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-2-oxo-1,8-naphthyridin-4-yl)acetamide

Produkt 1

HCID 11168248N-[3-chloro-7-(2-chlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

The product of EXAMPLE 69 (85 mg) was combined with methanol (7 mL), THF (4 mL) water (2 mL) and triethylamine (2 mL) at room temperature. After 1.5 hours the reaction was concentrated and the residue dissolved in EtOAc. The solution was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4). The concentrated residue was purified by flash chromatography on silica gel eluted with 0-50% EtOAc in hexane affording the title compound. HPLC/MS: 513.9 (M+I), 515.9 (M+3); Rt=4.05 min.

Aufarbeitung

  1. concentrationAfter 1.5 hours the reaction was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe solution was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customThe concentrated residue was purified by flash chromatography on silica gel
  6. washeluted with 0-50% EtOAc in hexane affording the title compound

Quellen und Nachweise

ORD-Eintrag
ord-34c8236bfae743d2ab6c0e16a8b1bcc4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

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