Chloroform → HCID 76618687, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added 5-[1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-piperazin-1-yl-thiazol-4-one (51, mg, 94 μL) from Example 23, chloroform (5 mL), acetyl chloride (1.5 equiv, 10 μL) and TEA (3 equiv, 40 μL). The reaction solution was stirred at 45° C. for 1.5 hours. The solution was then diluted with EtOAc (75 mL) and filtered through a Buchner funnel to remove excess K2CO3. The solution was washed with aq NH4Cl (50 ml×2), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2, DCM/MeOH 100:0 to 94:06) to provide the title compound (19 mg, 40% yield). 1H NMR (CDCl3) δ 7.95-7.97 (2H, m), 7.84 (2H, d, J=7.7 Hz), 7.77 (1H, s), 7.08-7.11 (2H, m), 6.87 (1H, d, J=8.2 Hz), 5.44 (2H, s), 4.09-4.11 (2H, m), 3.97 (3H, s), 3.79-3.81 (2H, m), 3.61-3.66 (4H, m), 2.17 (3H, s), 1.60 (3H, s); MS (ESI) 588 (MH+).

Provenance & Evidence