反应详情

2-[3,3-Diethoxypropylamino]-4-methoxyquinoline (0.046 g, 0.15 mmol) in THF (4 ml) was treated with 0.5M HCl (2 ml) for 10 min. The reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml) was added NaOAc (0.024 g, 0.3 mmol), 2-(3,4-dichlorophenyl)azetidine (0.03 g) and sodium cyanoborohydride (0.009 g, 0.15 mmol). After reaction for 40 min at 20° C., the reaction was evaporated to dryness under reduced pressure, and the residue partitioned between ethyl acetate and sat. sodium bicarbonate. The organic layer was dried, evaporated to dryness under reduced pressure and purified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (50 mg, 80%); δH (CD3OD) 1.55 (2H, m), 2.0 (1H, m), 2.25 (1H, m), 2.45-2.7 (2H, m), 2.8 (1H, m), 3.2-3.4 (4H, m), 3.9 (3H, s), 3.95 (1H, t), 6.0 (1H, s), 7.05 (1H, t), 7.15-7.5 (5H, m), 7.8 (1H, d); MS (ES+) 416/418 (47/32%, MH+), 244 (50), 201 (100).

1. customThe reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml)
2. customAfter reaction for 40 min at 20° C.
3. customthe reaction was evaporated to dryness under reduced pressure
4. customthe residue partitioned between ethyl acetate and sat. sodium bicarbonate
5. customThe organic layer was dried
6. customevaporated to dryness under reduced pressure
7. custompurified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane