GSK1292263 (HCl) synthesis

Yield:1032824-54-6 65%

Reaction Conditions:

with hydrogenchloride in tetrahydrofuran;1,4-dioxane at 20;

Steps:

169.3 5-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine hydrochloride

A mixture of the resulting white solid (50 mg, 0.11 mmol) in THF (3 mL) was stirred at ambient temperature as 4N HCl in dioxane (28 μL) was added dropwise. The resulting white precipitate was filtered, air-dried, then triturated with diethyl ether to give 35 mg (65%) of the title compound as a white solid. ¹H NMR (400 MHz, CDCl₃): δ 8.46 (d, 1H, J=0.7 Hz), 8.18 (bs, 2H), 8.05 (bs, 2H), 7.83 (bs, 1H), 7.61-7.45 (m, 1H), 4.24 (d, 2H, J=10.4 Hz), 4.00 (d, 2H, J=0.6 Hz), 3.21-3.03 (m, 5H), 2.89 (m, 1H), 2.15 (d, 1H, J=1.1 Hz), 1.96 (bs, 2H), 1.50 (bs, 2H), 1.28 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 457 (M+H).

References:

US2010/29650,2010,A1 Location in patent:Page/Page column 82