1-((4-Methoxyphenyl)sulfonyl)piperazine → 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one
Reaction equation
Br[CH:2]([C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(#N)C>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]2[CH2:31][CH2:30][N:29]([CH:2]([C:4]3[NH:13][C:12](=[O:14])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH3:3])[CH2:28][CH2:27]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1Participants
4
Procedure
In a flask containing of 2-(1-bromo-ethyl)-3H-quinazolin-4-one (500.0 mg, 0.20 mmol) in acetonitrile (20 ml) was added KI (496.0 mg, 0.30 mmol), and 1-(4-methoxy-benzenesulfonyl)-piperazine (509.6 mg, 0.20 mmol). The reaction was heated for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between water (20 ml) and dichloromethane (20 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solvent was removed under vacuum. The resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane. The product was collected and dried under reduced pressure to give 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one (Yield 385.0 mg, 45.18%). 1H NMR (400 MHz, DMSO-6): δ 1.25 (d, 3H, J=6.82 Hz), 2.67-2.56 (m, 4H), 2.88 (s, br, 4H), 3.85 (s, 3H), 3.53 (q, 1H, J=13.89, 6.82 Hz), 7.15 (d, 2H, J=8.84), 7.34 (t, 1H, J=7.33 Hz), 7.51 (d, 1H, J=8.34 Hz), 7.68-7.61 (m, 3H), 8.00 (d, 1H, J=7.83 Hz). MS m/z calc. 428.15, found (ESI); 429.4 (M+1)+. Retention time 2.68 minutes.