反应详情

温度

65 °C

A solution of N-(4-aminobutyl)-N-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-5,6,7,8-tetrahydro-quinolin-8-amine tetrahydrochloride, Z, (0.20 g, 0.38 mmol) in 1,2-dichloroethane (10 mL) was treated with Hünigs base (0.08 mL, 0.42 mmol), 2-pyridine carboxaldehyde (0.04 mL, 0.42 mmol), sodium triacetoxyborohydride (0.12 g, 0.57 mmol) and a catalytic amount of acetic acid (2 drops). The resulting mixture was warmed to 65° C. and stirred for 18 h. The reaction mixture was cooled to room temperature. A saturated aqueous solution of sodium bicarbonate was added. The product was extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-15% methanol/CH2Cl2) to afford 0.08 g (45% yield) of the desired product AB: 1H NMR (400 MHz, CDCl3) δ 8.54-8.34 (m, 2H), 8.15 (bs, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.60-7.52 (m, 1H), 7.45 (t, J=7.2 Hz, 2H), 7.39-7.32 (m, 1H), 7.32-7.22 (m, 2H), 7.14-7.04 (m, 1H), 7.02-6.84 (m, 1H), 4.15-4.04 (m, 1H), 3.92-3.70 (m, 4H), 2.82-2.50 (m, 6H), 2.15-2.04 (m, 1H), 2.04-1.82 (m, 1H), 1.82-1.78 (m, 1H), 1.70-1.40 (m, 5H); ESI+ MS: m/z (rel intensity) 468.3 (100, [M+H]+)

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThe product was extracted with dichloromethane
3. washThe combined organic layers were washed with brine
4. dry with materialdried over potassium carbonate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by silica gel chromatography (0-15% methanol/CH2Cl2)