Dopamine D1 receptor agonist compounds
A receptor stimulant, dopamine technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., can solve problems such as abnormalities
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Embodiment 1
[0024] a) 1-(benzofuran-7-yl)-2-[2-(2-chloro-3,4-dimethoxyphenyl)ethylamino]ethanol
[0025] A solution of 2-chloro-3,4-dimethoxyphenylethylamine (6.35g, 0.0296mol) and (7-benzofuryl)oxirane (4.29g, 0.0268mol) in 15ml of acetonitrile Reflux for 16 hours. The reaction mixture was cooled to 0°C (ice bath). Filtration and recrystallization of the crude product from hot acetonitrile afforded the title compound (3.52 g, 35%) as a white crystalline solid. 1 H-NMR (CDCl 3 )[δ, ppm]: 2.86-3.16 (m, 6H); 3.85 (s, 6H); 5.26 (dd, 1H); 6.73-6.77 (m, 2H); 6.91 (d, 1H); m, 1H); 7.39(d, 1H); 7.51(d, 1H); 7.61(d, 1H).
[0026] b) 1-(benzofuran-7-yl)-6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine
[0027] 1-(benzofuran-7-yl)-2-[2-(2-chloro-3,4-dimethoxyphenyl) in 70ml trifluoroacetic acid was treated with concentrated sulfuric acid (0.71ml, 0.0135mol) ) ethylamino]ethanol (2.20 g, 5.85 mmol), and stirred at room temperature for 90 minutes. The solution was evaporated in vacuo...
Embodiment 2
[0033] a) 1-(Benzo[b]thiophen-7-yl)-2-[2-(2-chloro-3,4-dimethoxyphenyl)ethylamino]ethanol
[0034] A mixture of 2-chloro-3,4-dimethoxyphenylethylamine (7.00g, 32.5mmol) and 7-benzo[b]thienyloxirane (5.30g, 30.1mmol) in 20ml of acetonitrile The solution was refluxed for 72 hours. The reaction mixture was cooled to 0°C (ice bath), filtered and the crude product recrystallized from hot acetonitrile to afford the title compound (5.57 g, 47%) as a white crystalline solid. 1 H-NMR (CDCl 3 )[δ, ppm]: 2.83-3.08(m, 6H); 3.84(s, 3H); 3.85(s, 3H); 5.06(m, 1H); 6.73(d, 1H); 6.88(d, 1H) ; 7.35 (m, 3H); 7.43 (d, 1H); 7.73 (m, 1H).
[0035] b) 1-(Benzo[b]thiophen-7-yl)-6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine
[0036] 1-(Benzo[b]thiophen-7-yl)-2-[2-(2-chloro-3 , 4-dimethoxyphenyl)ethylamino]ethanol (3.90 g, 10 mmol), and the solution was heated to reflux for 18 hours. The solution was evaporated in vacuo and the residue was dissolved in dichloromethane (100ml), the re...
Embodiment 3
[0041] a) 2-(2-chloro-3,4-dimethoxyphenyl)ethylamino]-1-indan-5-yl-ethanol
[0042] To a solution of 2-indan-5-yloxirane (3.38 g, 21.1 mmol) in anhydrous acetonitrile (20 ml) was added 2-(2-chloro-3,4-dimethoxyphenyl) Ethylamine (2.0 g, 23.2 mmol), and the solution was refluxed for 20 hours. Upon cooling a white precipitate formed which was collected by filtration and washed with diethyl ether to give the title compound as a white solid (2.85 g, 36%).
[0043] 1 H NMR (400 MHz, DMSO-d6): δ (ppm) 1.96-2.03 (2H, m, CH 2 -CH 2 -CH 2 ), 2.50-2.84 (10H, m, 5xCH 2 ), 3.72 (3H, s, CH 3 O), 3.80 (3H, s, CH 3 O), 4.56 (1H, t, J 6.04, H-1), 5.14 (1H, broad, NH) and 6.94-7.14 (5H, m, Ar-H). This material was used in the next reaction without further purification.
[0044] b) 1-indan-5-yl-6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine
[0045] 2-[(2-Chloro-3,4-dimethoxyphenyl)ethylamino]-1-indan-5-yl-ethanol (2.7g, 7.18mmol) was dissolved in trifluoroacetic acid (50m...
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