Dichloromethane → HCID 59993356, compound

Participants

Reaction Steps

3-Methyl-2-[1-(piperidin-4-ylamino)-ethyl]-3H-quinazolin-4-one (57.2 mg, 0.2 mmol) and triethylamine (167 μL, 0.4 mmol) were dissolved in dioxane (1 mL) and to this was added 4-methoxybenzenesulfonyl chloride (62 mg, 0.3 mmol). The reaction was shaken at room temperature overnight. Dichloromethane (2 mL) and water (2 mL) were added and the reaction tube was shaken. The top aqueous layer was aspirated off and the organic layer was concentrated in vacuo. The residue was dissolved in DMSO and purified by HPLC to yield the final product, 2-{1-[1-(4-Methoxy-benzenesulfonyl)-piperidin-4-ylamino]-ethyl}-3-methyl-3H-quinazolin-4-one. HPLC ret. time 2.23, 10-99% CH3CN, 5 min run; 1H NMR (CDCl3) δ 1.55 (d, 3H, J=6.6 Hz), 1.66 (q, 2H, J=12.1 Hz), 2.16 (m, 4H), 3.19 (m, 1H), 3.53 (s, 3H), 3.68 (m, 2H), 3.80 (s, 3H), 4.86 (q, 1H, J=5.7 Hz), 7.12 (d, 2H, J=9.0 Hz), 7.57 (t, 1H, J=8.1 Hz), 7.63 (d, 2H, J=8.9 Hz), 7.69 (d, 1H, J=7.7 Hz), 7.86 (t, 1H, J=8.4 Hz), 8.15 (dd, 1H, J=8.0, 1.2 Hz); ESI-MS m/z 457.4 (M+1)+.

Provenance & Evidence