Acetonitrile → HCID 22221501, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 29C and 2-chloromethyl-1H-benzoimidazole (0.88 mg) were combined and dissolved in DMF (7 mL)/triethylamine (1.5 mL). After stirring at 23° C. for 2 hours, the mixture was treated with acetonitrile (20 mL) and then allowed to stir for 24 hours. The reaction mixture was partitioned between CH2Cl2 (100 mL)/n-butanol (5 mL) and water (800 mL)/NH4OH (5 mL). The organic phase was separated, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography to provide the title as a white solid (1.169 g (55%). mp 62-64° C.; Rf=0.26 (95:5 CH2Cl2:methanol:0.1% NH40H); MS 400 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 12.3 (bs, NH, 1H), 7.90 (d, 1H, J=3 Hz), 7.55 (m, 1H), 7.3-7.5 (m, 8H), 7.15 (m, 2H), 6.80 (d, 1H, J=9 Hz), 5.05 (s, 2H), 3.76 (s, 2H), 3.39 (t, 4H, J=5.1 Hz), 2.57 (t, 4H, J=5.1 Hz).

Provenance & Evidence