4-(3-Iodobenzyl)morpholine → (4-Methyl-pyridin-2-yl)-{6-[2-(3-morpholin-4-ylmethyl-phenyl)-oxazol-5-yl]-pyridin-2-yl}-amine hydrochloride

Participants

Reaction Steps

4-(3-Iodo-benzyl)-morpholine was prepared as described for 1-(3-iodo-benzyl)-pyrrolidine above. (4-Methyl-pyridin-2-yl)-{6-[2-(3-morpholin-4-ylmethyl-phenyl)-oxazol-5-yl]-pyridin-2-yl}-amine was then prepared as for (4-methyl-pyridin-2-yl)-{6-[2-(3-pyrrolidin-1-ylmethyl-phenyl)-oxazol-5-yl]-pyridin-2-yl}-amine hydrochloride above using (4-methyl-pyridin-2-yl)-(6-oxazol-5-yl-pyridin-2-yl)-amine (Example 008), 4-(3-iodo-benzyl)-morpholine, Pd(PPh3)4, LiOtBu and anhydrous 1,4-dioxane then HCl (2M in ether) to afford the title compound as a beige solid (8%). 1H NMR (400 MHz, DMSO-d6) δ 12.69-11.90 (m, 1H), 11.90-11.22 (m, 1H), 8.51 (s, 1H), 8.46 (d, J=5.8 Hz, 1H), 8.28 (s, 1H), 8.22 (d, J=7.7 Hz, 1H), 8.05 (t, J=7.9 Hz, 1H), 7.85 (d, J=7.5 Hz, 1H), 7.75 (d, J=7.7 Hz, 1H), 7.70 (t, J=7.7 Hz, 1H), 7.57 (s, 1H), 7.41 (d, J=8.3 Hz, 1H), 7.19 (d, J=4.5 Hz, 1H), 4.47 (s, 2H), 3.95 (d, J=11.8 Hz, 2H), 3.85 (t, J=11.8 Hz, 2H), 3.27 (d, J=11.8 Hz, 2H), 3.20-3.10 (m, 2H), 2.50 (s, 3H). (ESI+) m/z 428 (M+H)+. Retention time=1.80 mins (method 1).

Provenance & Evidence