3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine → N-(3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1393945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393945
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:18])[CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33](Cl)=[O:34])[C:28]2=[O:36])=[CH:23][CH:22]=1>ClCCl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:33]([C:29]2[C:28](=[O:36])[N:27]([C:24]3[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=3)[CH:32]=[CH:31][CH:30]=2)=[O:34])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[C:15]([CH3:18])[CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1

Komponenten

5

Edukt 2

HCID 210816133-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineHCID 596809561-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride

Produkt 1

HCID 16739700N-(3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine (62 mg, 0.24 mmol) in dichloromethane (2 mL) and pyridine (0.5 mL), was added dropwise a solution of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride (30 mg, 0.12 mmol) in dichloromethane (0.5 mL). The reaction mixture was stirred at rt for 30 min, and then concentrated to dryness. The residue was washed with methanol. The solid that formed was collected by filtration and dried under vaccum to give the title compound (35 mg, 61%). 1H NMR (DMSO-d6) δ 12.10 (br s, 1H), 8.58 (dd, 1H, J=7.15, 2.20 Hz), 8.12 (dd, 1H, J=6.60, 1.65 Hz), 7.98 (s, 1H), 7.95 (d, 2H, J=2.75 Hz), 7.62-7.58 (m, 2H), 7.40-7.47 (m, 4H), 6.78 (d, 1H, J=2.75 Hz), 6.72 (t, 1H, J=7.15 Hz), 2.54 (s, 3H); MS(ESI+) m/z 474.23 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. washThe residue was washed with methanol
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under vaccum

Quellen und Nachweise

ORD-Eintrag
ord-b2ba73768861436891a148f409acedee
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348325B2

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