1,1'-Carbonyldiimidazole → 5-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

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Reaction Steps

6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine (4-4, 0.046 g, 0.094 mmol) was dissolved in 1 ml DCM and 1,1′-carbonyldiimidazole (0.017 g, 0.104 mmol) was added. After 8 h additional 1,1′-carbonyldiimidazole (0.017 g, 0.104 mmol) was added. After stirring overnight the reaction was diluted with saturated aqueous Na2CO3. The mixture was extracted 3× with DCM then 1× with iso-BuOH. Purification by flash column chromatography (95:5 to 90:10 DCM/MeOH) afforded 5-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (4-5). 1H NMR (CDCl3) δ 7.69 (m, 1H), 7.55 (m, 1H), 7.27-7.16 (m, 9H), 7.08 (m, 2H), 6.76 (s, 1H), 4.12 (m, 1H), 3.34 (s, 2H), 2.96 (d, 2H), 2.61 (s, 3H), 2.52 (m, 2H), 2.27 (m, 2H), 1.79 (d, 2H, J=10.0 Hz). MS m/z (M+H)=515.16.

Provenance & Evidence