Cyclohexanol → HCID 59993331, compound

Participants

Reaction Steps

2-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-ylmethyl]-3H-quinazolin-4-one (83 mg, 0.2 mmol) in POCl3 (1 mL) was heated to 90° C. for 2 hours. Then the excess POCl3 was removed in vacuo. The residue was dissolved in toluene (5 mL) and then the solvent was removed in vacuo. This step was repeated twice more. The residue was then dissolved in THF (1 mL) and cyclohexanol (211 μL, 2 mmol) was added. The reaction was stirred at room temperature for 1 day. The reaction mixture was partitioned between dichloromethane and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by HPLC (in the absence of TFA). 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=7.5 Hz, 1H), 7.89 (d, J=8.3 Hz, 1H), 7.79 (t, J=7.3 Hz, 1H), 7.72 (dt, J=9.5, 2.4 Hz, 2H), 7.52 (t, J=7.4 Hz, 1H), 7.01 (dt, J=9.5, 2.4 Hz, 2H), 5.39 (quintet, J=4.2 Hz, 1H), 3.90 (m, 5H), 3.16 (m, 4H), 2.90 (m, 4H), 1.66 (m, 10H); HPLC ret. time 2.93 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 497.3 (M+1)+.

Provenance & Evidence