Acetic Acid → (5-Phenyl-thiazol-2-yl)-(6-piperidin-1-ylmethyl-pyridin-2-yl)-amine

Participants

Reaction Steps

6-(5-Phenyl-thiazol-2-ylamino)-pyridine-2-carbaldehyde (6-5, 0.025 g, 0.088 mmol) was dissolved in 1 mL dichloroethane. Piperidine (0.014 mL, 0.14 mmol), acetic acid (0.010 mL) and NaBH(OAc)3 (0.030 g, 0.14 mmol) were added. The reaction was stirred at room temperature for 1 h. The reaction was then diluted with CH2Cl2, washed with water and extracted 1× with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, concentrated. Purification by reverse phase HPLC afforded the titled compound. 1H NMR (CDCl3): δ9.94 (bs, 1H), 7.61 (m, 4H), 7.59 (d, 2H, J=8.0 Hz), 7.41 (t, 2H, J=7.5 Hz), 7.29 (d, 1H, J=7.3 Hz), 7.06 (d, 1H, J=7.4 Hz), 6.77 (d, 1H, J=8.1 Hz), 3.73 (s, 2H), 2.56 (bs, 4H), 1.64 (m, 4H), 1.26 (m, 2H). M+1: 351.1.

Provenance & Evidence