Hydrochloric Acid → 5-(3-{2-[(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo-[1,2-a]pyridin-2-yl)-2-(methyloxy)benzonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-2-(methyloxy)benzonitrile (Intermediate Example 4) (2.02 g, 5.57 mmol) and 3-{[2-(dimethylamino)ethyl]-oxy}aniline dihydrochloride (1.67 g, 6.58 mmol) in trifluoroethanol (20 mL) was added HCl (0.700 mL, 4M in dioxane, 2.8 mmol). The reaction was stirred at 84° C. for 2 days. The reaction was poured into half saturated NaHCO3, extracted with DCM and EtOAc, dried (MgSO4), concentrated and triturated with diethyl ether to provide the title compound (2.63 g, 5.18 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.17 (s, 6H), 2.57 (t, J=5.7 Hz, 2H), 3.96 (s, 5H), 6.55 (d, J=8.4 Hz, 1H), 6.63 (d, J=5.1 Hz, 1H), 7.07 (t, J=7.0 Hz, 1H), 7.16 (t, J=8.1 Hz, 1H), 7.26 (d, J=8.4 Hz, 1H), 7.33 (d, J=9.2 Hz, 1H), 7.45-7.53 (m, 2H), 7.74 (d, J=9.2 Hz, 1H), 7.92 (dd, J=9.0, 2.0 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H), 8.39 (d, J=5.1 Hz, 1H), 9.49 (d, J=6.2 Hz, 1H), 9.77 (s, 1H).

Herkunft & Nachweise