N'-(6-Chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

HRID 456059

Reaktionsgleichung

Reaktionsgleichung von HRID 456059
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:10](=O)[CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)=[CH:4][CH:3]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:8]=2)[N:7]=1

Komponenten

3

Edukt 1

HCID 86652010N'-(6-Chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide

Produkt 1

HCID 249683676-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of N′-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide (8 g crude, 25.5 mmol) in 250 mL acetic acid was heated at 50° C. for 5 hours. After the reaction was completed, the solvent was evaporated and the crude was dissolved in EtOAc and filtered. The solid was mainly the impurity dicyclohexyl urea and the product dissolved in EtOAc. Solvent was evaporated and resulted the title compound as a yellow solid (4 g, 53%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.82 (d, 1H), 8.33 (d, 1H), 8.25 (d, 1H), 8.0 (d, 1H), 7.93 (s, 1H), 7.83 (d, 1H), 7.53 (m, 1H), 7.42 (d, 1H), 4.79 (s, 2H). LCMS (method A): [MH]+=296.0, tR=1.88 min.

Aufarbeitung

  1. customthe solvent was evaporated
  2. dissolutionthe crude was dissolved in EtOAc
  3. filtrationfiltered
  4. dissolutionthe product dissolved in EtOAc
  5. customSolvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9eb8e703367346f2ae32c48ec3d51192
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

Verknüpfte Notizen

Wird geladen…