Hydrochloric Acid → (4-Methyl-pyridin-2-yl)-{6-[2-(3-pyrrolidin-1-ylmethyl-phenyl)-oxazol-5-yl]-pyridin-2-yl}-amine hydrochloride

Participants

Reaction Steps

(4-Methyl-pyridin-2-yl)-{6-[2-(3-pyrrolidin-1-ylmethyl-phenyl)-oxazol-5-yl]-pyridin-2-yl}-amine was then prepared as for 4-(2-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile above using (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine (Example 008), 1-(3-iodo-benzyl)-pyrrolidine, Pd(PPh3)4, LiOtBu and anhydrous 1,4-dioxane. The isolated material was taken up in EtOAc and treated with HCl (2M in ether) to afford the title compound as a beige solid (35%) after evaporation under vacuum. 1H NMR (400 MHz, DMSO-d6) δ 12.65 (s, 1H), 11.30 (s, 1H), 8.53-8.47 (m, 2H), 8.33 (s, 1H), 8.19 (d, J=7.6 Hz, 1H), 8.07 (t, J=7.9 Hz, 1H), 7.85 (d, J=7.8 Hz, 1H), 7.80 (d, J=7.6 Hz, 1H), 7.67 (t, J=7.7 Hz, 1H), 7.52 (s, 1H), 7.38 (d, J=8.3 Hz, 1H), 7.24 (d, J=6.4 Hz, 1H), 4.48 (d, J=5.6 Hz, 2H), 3.42-3.29 (m, 4H), 2.51 (s, 3H), 2.09-1.86 (m, 4H). (ESI+) m/z 412 (M+H)+. Retention time=1.88 mins (method 1).

Provenance & Evidence