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

HRID 69176

Reaktionsgleichung

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([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)=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[CH:24]([NH2:28])([CH2:26][CH3:27])[CH3:25]>CN1C(=O)CCC1.CCOC(C)=O>[CH:24]([NH:28][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([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)=[CH:9][N:10]=2)[N:7]=1)([CH2:26][CH3:27])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

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)).

Aufarbeitung

washwashed with 1 M Na2CO3 (×1) and water (×2)
extractionThe aqueous was further extracted with EtOAc (2×)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography (Flashmaster)
customcrystallized in Et2O

Quellen und Nachweise

ORD-Eintrag: ord-5f151d11ce1f41bfaabc1b24c412ecbb
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822468B2

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