反应详情

Methanol (30 ml) and 5% palladium/carbon (0.20 g) are added to a mixture (2.32 g) of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]benzimidazole, and the solution is stirred at room temperature under a nitrogen environment until the raw materials dissolved. Solid materials are separated through filtration. The filtrate is concentrated and a residue is obtained. The residue is purified through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=85/15), and 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole are separated. These materials are crystallized in mixed solvents of chloroform and diethylether. The crystals are separated through filtration, dried and thus, 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (0.354 g) (197) and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (0.330 g) (198) are obtained. 1H-NMR (CDCl3, δ): 3.00 (3H, s), 4.98 (2H, s), 5.88 (2H, s), 7.55 (2H, d, J=8.6 Hz), 7.69 (2H, d, J=8.6 Hz), 7.90 (1H, d, J=8.6 Hz), 7.96 (1H, dt, J=7.1 and 0.6 Hz), 8.12 (1H, J=8.0 Hz), 8.18 (1H, dd, J=8.5 and 1.4 Hz), 8.55 (1H, dt, J=8.0 and 1.7 Hz), 8.62 (1H, d,J=1.1 Hz), 8.77(1H, dd, J=5.9 and 1.1 Hz).

1. dissolutiondissolved
2. customSolid materials are separated through filtration
3. concentrationThe filtrate is concentrated
4. customa residue is obtained
5. customThe residue is purified through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=85/15), and 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole
6. customare separated
7. customThese materials are crystallized in mixed solvents of chloroform and diethylether
8. customThe crystals are separated through filtration
9. customdried