1',3'-disubstituted-4-pheny-3,4,5,6-tetrahydro-2h,1'h-[1,4']bipyridinyl-2'-ones
a technology of disubstituted phenyls and dipyridinyls, which is applied in the field of pyridinonederivatives, can solve problems such as glutamatergic neurotransmission imbalan
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example 1
3′-Chloro-1′-cyclopropylmethyl-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-one (E1)
[0169]
[0170]A solution of intermediate D18 (0.2 g, 0.65 mmol) and N-chlorosuccinimide (0.09 g, 0.65 mmol) in DCM (10 ml) was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo and the crude product was purified by column chromatography (silica gel; 0-3% methanol / DCM as eluent). The desired fractions were collected and evaporated in vacuo and the resulting solid was recrystallized from diethyl ether to yield compound E1 (0.10 g, 47%) as a white solid.
[0171]Melting point: 170.8° C.
[0172]1H NMR (400 MHz, CDCl3) 8 ppm 0.35-0.42 (m, 2H), 0.57-0.64 (m, 2H), 1.19-1.33 (m, 1H), 1.85-2.00 (m, 4H), 2.64-2.76 (m, 1H), 2.85-2.99 (m, 2H), 3.76-3.87 (m, 4H), 6.05 (d, J=7.6 Hz, 1H), 7.19-7.29 (m, 4H), 7.29-7.38 (m, 2H).
example 2
1′-Butyl-3′-chloro-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-one (E2)
[0173]
[0174]A solution of intermediate D19 (0.43 g, 1.40 mmol) and N-chlorosuccinimide (0.19 g, 1.40 mmol) in DCM (10 ml) was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo and the crude product was purified by column chromatography (silica gel; 0-3% methanol / DCM as eluent). The desired fractions were collected and evaporated in vacuo and the resulting solid was recrystallized from diethyl ether to yield compound E2 (0.39 g, 82%) as a white solid.
[0175]Melting point: 149.4° C.
[0176]1H NMR (400 MHz, CDCl3) 8 ppm 0.95 (t, J=7.3 Hz, 3H), 1.31-1.42 (m, 2H), 1.68-1.78 (m, 2H), 1.85-1.98 (m, 4H), 2.64-2.73 (m, 1H), 2.87-2.96 (m, 2H), 3.82 (br d, J=12.1 Hz, 2H), 3.93 (t, J=7.3 Hz, 2H), 6.03 (d, J=7.6 Hz, 1H), 7.10 (d, J=7.6 Hz, 1H), 7.19-7.28 (m, 3H), 7.29-7.37 (m, 2H).
example 3
3′-Bromo-1′-cyclopropylmethyl-4-phenyl-3,4,5,6-tetrahydro-2H,1′H-[1,4′]bipyridinyl-2′-one (E3)
[0177]
[0178]N-Bromosuccinimide (0.145 g, 0.82 mmol) was added to a solution of intermediate D18 (0.25 g, 0.82 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the solvent was evaporated in vacuo and the crude residue was purified by column chromatography (silica gel; 0-3% methanol / DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield compound E3 (0.20 g, 64%) as a white solid.
[0179]Melting point: 150° C.
[0180]1H NMR (500 MHz, DMSO-d6) 8 ppm 0.34-0.40 (m, 2H), 0.44-0.50 (m, 2H), 1.16-1.26 (m, 1H), 1.77 (qd, J=12.38, 3.61 Hz, 2H), 1.88 (br d, J=12.1 Hz, 2H), 2.68-2.78 (m, 1H), 2.91 (br t, J=11.9 Hz, 2H) 3.69 (br d, J=12.1 Hz, 2H), 3.74 (d, J=7.2 Hz, 2H), 6.21 (d, J=7.5 Hz, 1H), 7.19-7.25 (m, 1H), 7.27-7.36 (m, 4H), 7.69 (d, J=7.5 Hz, 1H).
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