Aminoaryl sulphonamide derivatives as functional 5-ht6 ligands
A technology of amino and benzenesulfonyl groups, applied in the field of aminoarylsulfonamide derivatives
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Embodiment 1
[0173] Example 1: 1-[3-(1-methylpiperidin-4-yl)amino]benzenesulfonyl-1H-indole
[0174] N-methyl 4-piperidone (8.99mmol, 1.01g) and sodium sulfate (44.98mmol, 6.388g) were added to 1-(3-aminobenzenesulfonyl) indole (4.49mmol, 1.0 g) In solution in 20 mL of acetic acid. The reaction mixture was stirred at 25°C for 1 hour. After 1 hour, sodium triacetoxyborohydride (13.47 mmol, 3.3 g) was added in small portions over 30 minutes. After complete addition of sodium triacetoxyborohydride, the reaction was stirred at 250° C. for 24 hours. After completion of the reaction (TLC), the reaction mixture was poured onto ice-water mixture, basified with 20% NaOH solution and the mixture was extracted with ethyl acetate (2 x 60 mL). The combined ethyl acetate extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. Volatiles were removed under reduced pressure to give a crude viscous oil. The mixture was purified on a silica gel column with ethyl acetate an...
Embodiment 2
[0175] Example 2: 1-[3-(1-methylpiperidin-4-yl)amino]benzenesulfonyl-5-methoxyindole
[0176] Using a method analogous to that given in the preparation of Example 1 with some non-critical changes, the above derivatives were prepared. IR spectrum (Cm -1 ): 1145, 1225, 1336, 3374; mass spectrum (m / z): 400.4 (M+H) + ; 1 H-NMR (δ, ppm): 1.39-1.48 (2H, m), 1.90-1.97 (2H, m), 2.09-2.17 (2H, m), 2.32 (3H, s), 2.79-2.82 (2H, m ), 3.18-3.2 (1H, m), 3.75-3.77 (1H, d, J=7.74Hz), 3.81 (3H, s), 6.57-6.58 (1H, d, J=3.66Hz), 6.61-6.66 ( 1H, m), 6.90-6.93(2H, m), 6.97-6.979(1H, d, J=2.416Hz), 7.098-7.18(2H, m), 7.482-7.491(1H, d, J=3.65Hz) , 7.881-7.9 (1H, d, J = 9.1 Hz).
Embodiment 3
[0177] Example 3: 1-[3-(1-methylpiperidin-4-yl)amino]benzenesulfonyl-5-isopropoxyindole
[0178] Using a method analogous to that given in the preparation of Example 1 with some non-critical changes, the above derivatives were prepared. IR spectrum (Cm -1 ): 1147, 1455, 1601, 2936, 3403; mass spectrum (m / z): 428.4 (M+H) + ; 1 H-NMR (δ, ppm): 1.31-1.33 (d, 6H, J = 6.07Hz), 1.41-1.47 (2H, m), 1.9-1.93 (2H, d, J = 12.06Hz), 2.08-2.14 ( 2H, m), 2.31 (3H, s), 2.79-2.81 (2H, d, J = 11.32Hz), 3.18-3.2 (1H, m), 3.76-3.78 (1H, d, J = 7.71Hz), 4.48 -4.52 (q, 1H), 6.55-6.55 (1H, d, J=3.58Hz), 6.63-6.66 (1H, dd), 6.88-6.91 (1H, d, J=2.43, 2.4 and 9.0Hz), 6.92 -6.92 (1H, t, J = 1.82 and 1.62Hz), 6.97-6.98 (1H, d, J = 2.34Hz), 7.07-7.18 (2H, m), 7.46-7.47 (1H, d, J = 3.6Hz ), 7.86-7.88 (1H, d, J=9.03Hz),
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