4-(Benzylamino)phenol → N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-acetamide

HRID 1029117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029117
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[CH2:17]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:18]1C=CC=CC=1.C(=O)([O-])[O-:33].[K+].[K+]>CN(C=O)C.CO>[O:12]=[C:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]2[C:8](=[N:9][CH:10]=[CH:11][C:2]=2[O:31][C:28]2[CH:29]=[CH:30][C:25]([NH:24][C:17](=[O:33])[CH3:18])=[CH:26][CH:27]=2)[NH:7]1

Komponenten

6

Edukt 3

HCID 76374-(Benzylamino)phenolHCID 11430Potassium CarbonateHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Produkt 1

HCID 69811669N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-acetamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 4-(benzylamino)phenol (78 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 136 (8 mg, 20% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 12.06 (s, 1H), 9.11 (d, 1H), 8.42 (dd, 1H), 8.26 (d, 1H), 7.82 (d, 1H), 6.99 (d, 2H), 6.70 (m, 3H), 6.48 (d, 1H), 6.42 (s, 2H).

Aufarbeitung

  1. filtrationfiltered through a membrane
  2. customThe crude product was purified via prep-LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-fd8e4c47e6204980a9226f8cb0f41443
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

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