3-(Bromomethyl)thiophene → 4,6-Dimethyl-pyrimidine-5-carboxylic acid ((r)-3-{4-[(4-chloro-phenyl)-thiophen-3-ylmethyl-amino]-piperidin-1-yl}-butyl)-amide

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A solution of the above aniline (119 mg, 0.29 mmol) and 3-(bromomethyl)thiophene (61 mg, 0.34 mmol) in CH3CN (5 mL) was stirred at room temperature overnight to afford COMPOUND 292 as a white solid (34 mg, 23%) following work-up and purification. 1H NMR (CDCl3) δ 0.89-1.19 (m, 2H), 1.01 (d, 3H, J=6.6 Hz), 1.54-1.58 (m, 1H), 1.73-1.80 (m, 3H), 2.16 (t, 1H, J=12.3 Hz), 2.52 (s, 6H), 2.56 (t, 1H, J=12.3 Hz), 2.73-2.89 (m, 3H), 3.28-3.36 (m, 1H), 3.49-3.57 (m, 1H), 3.82 (s, 2H), 3.84-3.92 (m, 1H), 6.54 (d, 2H, J=8.7 Hz), 6.98-7.01 (m, 2H), 7.06-7.09 (m, 2H), 7.28 (dd, 1H, J=4.8, 3.0 Hz), 8.71 (br s, 1H), 8.88 (s, 1H). ES-MS m/z 512 (M+H).

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