Cesium carbonate → N-{1-[6-(5-Methyl-thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidin-4-yl}-acetamide formate

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Reaction Steps

To a suspension of N-[1-(6-hydroxy-benzofuran-3-ylmethyl)-piperidin-4-yl]-acetamide (50 mg, 0.17 mmol), Cs2CO3 (170 mg, 0.52 mmol) in DMF (1.73 mL) was added 2-chloro-5-methyl-thiazolo[4,5-b]pyridine (40 mg, 0.22 mmol) and the reaction mixture was stirred (rt, 16 h). The reaction mixture was filtered and purified via reverse-phase preparative HPLC to provide the title compound as a white solid (67 mg, 79%). MS (ESI): mass calcd. for C23H24N4O3S, 436.16; m/z found, 437.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.91 (d, J=8.1, 1H), 7.83 (5, 1H), 7.71 (d, J=8.3, 1H), 7.63 (5, 1H), 7.32 (d, J=7.9, 1H), 7.09 (d, J=8.1, 1H), 5.77 (5, 1H), 3.93 (5, 3H), 3.17 (5, 2H), 2.61 (5, 3H), 2.47 (5, 2H), 1.97 (5, 5H), 1.78 (5, 2H).

Provenance & Evidence