1-((4-Methoxyphenyl)sulfonyl)piperazine → 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile

Participants

Reaction Steps

In a test tube containing of 2-(1-bromo-ethyl)-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile (40.0 mg, 0.14 mmol) in acetonitrile (2 ml) was added KI (34.0 mg, 0.21 mmol), and (1-(4-Methoxy-benzenesulfonyl)-piperazine (46.4 mg, 0.21 mmol). The reaction was heated for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between water (2 ml) and dichloromethane (5 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 dissolvent in DMSO (2 ml) and purified by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give the 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile compound (Yield 5.52 mg, 8.2%). 1H NMR (400 MHz, CDCl3): δ 1.64 (d, 3H, J=6.57 Hz), 3.29-3.10 (m, 6H), 3.48-3.37 (m, 2H), 3.68 (s, 3H), 3.90 (s, 3H), 4.53 (q, 1H, J=13.14, 5.81 Hz), 6.97 (d, 2H, J=2.02 Hz), 7.66 (d, 2H, J=8.84, Hz), 7.76 (d, 1H, J=8.59 Hz), 7.94 (dd, 1H J=8.59, 2.02 Hz), 8.57 (d, 1H, J=2.02 Hz). MS m/z calc. 467.16, found (ESI); 468.4 (M+1)+. Retention time 2.75 minutes.

Provenance & Evidence