Diisopropylethylamine → 2,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamide

HRID 1029144

Reaktionsgleichung

Reaktionsgleichung von HRID 1029144
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27](Cl)=[O:28].CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.O>[Cl:24][C:25]1[N:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:26]=1[C:27]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1)=[O:28]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27999962,5-Dichloro-nicotinoyl chlorideHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Produkt 1

HCID 581683272,5-Dichloro-N-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-nicotinamideAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

Compound 137 (40 mg, 0.13 mmol), 2,5-dichloro-nicotinoyl chloride (28 mg, 0.13 mmol), and DIEA (0.02 mL, 0.13 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O. The resulting precipitate was filtered, washed with EtOAc/H2O, and dried under vacuum to provide 180 (40 mg, 64% yield) as a white solid. LC-MS (M+H=478, obsd.=478).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with EtOAc/H2O
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6086b94094634432a2e6dc0c1eea5f42
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

Verknüpfte Notizen

Wird geladen…