Dimethylformamide → N-[1-(2-Morpholin-4-ylethyl)benzimidazol-2-yl]-3-nitrobenzamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-nitro-N-(1H-benzoimidazol-2-yl)-benzamide prepared above in Example 1 (150 mg, 0.532 mmol, 1.0 equiv) in 3 mL of 5:1 acetone:DMF was added 109 mg of 4-(2-chloroethyl)morpholine hydrochloride (0.585 mmol, 1.1 equiv) and 221 mg K2CO3 (1.60 mmol, 3.0 equiv). The resulting suspension was heated to 54° C. with stirring for 3 h. The suspension was then diluted with 10 mL sat. NaHCO3, and the acetone was removed under reduced pressure. The resulting suspension was then diluted with 20 mL CH2Cl2, shaken until no solids remained, and passed through a 20 mm (40 mL) 3M Empore octadecyl (C18) cartridge to remove water. The collected organics were then concentrated under reduced pressure. Purification by flash chromatography (SiO2, 2–4% MeOH/CH2Cl2) gave 124 mg of the product as a tan solid (0.314 mmol). 1H NMR (DMSO-d6, 400 MHz) δ 12.85 (s, 1 H), 8.97 (s, 1 H), 8.61 (d, J=7.6 Hz, 1 H), 8.38 (d, J=7.5 Hz, 1 H), 7.79 (t, J=8.0 Hz, 1 H), 7.58 (t, J=7.6 Hz, 2 H), 7.26 (m, 2 H), 4.42 (t, J=5.9 Hz, 2 H), 3.49 (m, 4 H), 2.75 (t, J=5.9 Hz, 2 H), 2.55 (m, 4 H).

Provenance & Evidence