反应详情

To a solution of 2-formyl-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide (0.3991 g, 1.5 mmol) and 2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione (0.4424 g, 1.3 mmol) in CH2Cl2 (13 mL) was added sodium triacetoxyborohydride (0.5539 g, 2.6 mmol), and the reaction stirred at room temperature for 22 hours. Saturated NaHCO3 (20 mL) was added and the aqueous phase was extracted with CH2Cl2 (2×100 mL), and the combined organic extracts were washed with brine (1×75 mL), dried (NaSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2—MeOH—NH4OH) provided 0.4564 g (52%) of 2-{[[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide as a yellow foam. 1H NMR (CDCl3) δ 1.28 (t, 2H, J=9 Hz), 1.49-1.52 (m, 2H), 1.74-1.81 (m, 6H), 1.91-2.00 (m, 1H), 2.11-2.20 (m, 1H), 2.50-2.73 (m, 7H), 2.92 (s, 2H), 2.95 (s, 4H), 3.52-3.57 (m, 2H), 4.17-4.22 (m, 2H), 4.32-4.37 (m, 1H), 4.81 (s, 1H), 6.95-6.98 (m, 1H), 7.27-7.28 (m, 1H), 7.68-7.70 (m, 2H), 7.79-7.82 (m, 2H), 8.32 (d, 1H, J=3 Hz).

1. extractionthe aqueous phase was extracted with CH2Cl2 (2×100 mL)
2. washthe combined organic extracts were washed with brine (1×75 mL)
3. dry with materialdried (NaSO4)
4. concentrationconcentrated
5. customPurification of the crude material by column chromatography on silica gel (33:1:1 CH2Cl2—MeOH—NH4OH)