4-Methylmorpholine → (S)-3-(6-bromo-4-methyl-1H-benzo[d]imidazol-2-yl)-4-(1-hydroxy-3-phenylpropan-2-ylamino)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(6-bromo-4-methyl-1H-benzimidazol-2-yl)-4-chloro-1H-pyridin-2-one (1.42 g, 3.78 mmol) in DMF (15 mL) were added (S)-(−)-2-amino-3-phenyl-1-propanol (1.43 g, 9.45 mmol) and N-methyl morpholine (1.5 mL). The reaction mixture was heated to 80° C. for 6 h and cooled to room temperature. The solvent was removed with high vacuum and the residue was purified by flash chromatography (5% MeOH/CH2Cl2) to yield the title compound (1.26 g, 74%) as a yellow foam. 1H NMR (300 MHz, CDCl3) δ 6.9–7.2 (8H, m), 5.86 (1H, d, J=7.1 Hz), 3.7–3.9 (3H, m), 2.9–3.1(2H, m), 2.57 (3H, s). LCMS (M+H)+ m/z 453 (t=2.03 min.).

Provenance & Evidence