Acetyl chloride → HCID 59993355, compound

Participants

Reaction Steps

To the 1 ml DMF solution of 6-Amino-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-3H-quinazolin-4-one (50.0 mg, 0.11 mmol) was added acetyl chloride (9.44 mg, 0.12 mmol). The reaction was stirred for 2 hours. The solvent was removed by reduce pressure and extracted with Na2CO3 aqueous and ethyl acetate, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished 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 N-(2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-acetamide (Yield 8.29 mg, 14.9%). 1H NMR (400 MHz, MeOD-d4): δ 1.70 (d, 3H, J=6.57 Hz), 2.18 (s, 3H), 3.57-3.43 (m, 8H), 3.64 (s, 3H), 3.93 (s, 3H), 4.84 (q, 1H, J=6.57, 6.06 Hz), 7.19 (d, 2H, J=9.09 Hz), 7.64 (d, 1H, J=8.34 Hz), 7.79 (d, 2H, J=9.09 Hz), 7.98 (dd, 1H, J=8.59, 2.78 Hz), 8.46 (d, J=2.27 Hz). MS m/z calc. 499.2 found (ESI); 500.2 (M+1)+. Retention time 2.42 minutes.

Provenance & Evidence