Reaktion #156358

Reaktionsgleichung

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline

KF

sec-butylamine

→

title compound

sec-Butyl-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-amine

Lösungsmittel

NMP

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1 M Na2CO3 (×1) and water (×2)
2. 2
   ExtraktionThe aqueous was further extracted with EtOAc (2×)
3. 3
   TrocknenThe combined organic layer was dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash chromatography (Flashmaster)
7. 7
   Sonstigecrystallized in Et2O

Vorschrift

6-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-quinoline (Example 14, 70 mg, 0.237 mmol), KF (70 mg, 1.187 mmol) and sec-butylamine (484 μL, 4.75 mmol) were suspended in NMP (1 mL). The RM was stirred at 180° C. for 29 h. The mixture was diluted with EtOAc and washed with 1 M Na2CO3 (×1) and water (×2). The aqueous was further extracted with EtOAc (2×). The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Flashmaster) and then crystallized in Et2O to afford the title compound as a beige solid (tR 4.28 min (conditions 4), MH+ 332.3, 1H-NMR in DMSO-d6: 8.83 (m, 1H); 8.25 (m, 1H); 7.92 (d, 1H); 7.83 (m, 1H); 7.70 (m, 1H); 7.61 (d, 1H); 7.48 (dd, 1H); 7.32 (s, 1H); 6.66 (d, 1H); 6.56 (d, 1H); 4.34 (s, 2H); 3.70 (m, 1H); 1.46 (m, 2H); 1.07 (d, 3H); 0.80 (t, 3H)).

Quelle