4-Methylmorpholine → 1-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

Participants

Reaction Steps

To a solution of 5′-chloro-3,5-dimethyl-2′-(piperazin-1-yl)-2,4′-bipyridine (2.3 g, 15.1 mmol) and HOBT (2.55 g, 18.9 mmol) in CH2Cl2 (60 mL) was added NMM (5.67 g, 56.7). After stirring for 30 min at room temperature, EDCI (3.63 g, 18.9 mmol) and 3-(methylsulfonyl)propanoic acid (3.9 g, 12.6 mmol) were added and the mixture was stirred at 30° C. for 18 hours. TLC (CH2Cl2/MeOH=10:1) showed the starting material was consumed completely. After removal of the solvent in vacuo, the residue was dissolved in CH2Cl2 (180 mL), washed with saturated aq. NaHCO3 (40 mL), saturate aq. NH4Cl (40 mL) and brine (40 mL). The resulting material was dried over Na2SO4 and concentrated in vacuo to give title compound (4.8 g, 90%) as white solid. 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.15 (s, 1H), 7.36 (s, 1H), 6.53 (s, 1H), 3.69-3.66 (m, 2H), 3.58-5.53 (m, 4H), 3.48-3.46 (m, 2H), 3.41-3.37 (m, 2H), 2.94 (s, 3H) 2.89-2.86 (m, 2H), 2.31 (s, 3H), 2.10 (s, 3H); m/z for C20H25ClN4O3S 437.3 (M+H)+.

Provenance & Evidence