Dimethylformamide → HCID 76618661, compound

Participants

Reaction Conditions

Reaction Steps

To a flask purged with N2 was added ′5-[1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-methylidene]-2-thioxo-thiazolidin-4-one, (1.12 g, 2.27 mmol), iodomethane (5.5 mL, 88 mmol) and DMF (35 mL). The solution was al lowed to stir at 40° C. for 20 h. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in MeCN (25 mL). To the mixture was added 1-methyl piperazine (0.76 mL, 6.8 mmol), and the solution was stirred at 65° C. for 2 h. The solution was then diluted with EtOAc (150 mL), washed with sat NH4Cl (70 mL×2), dried over Na2SO4, filtered and concentrated. The crude material was chromatographed (SiO2 DCM/MeOH 100:0 to 90:10) to provide the title product (470 mg, 37% yield). 1H NMR (DMSO-d6) δ 8.17 (1H, d, J=8.1 Hz), 8.11 (1H, s), 8.02 (1H, d, J=8.1 Hz), 7.61 (1H, s), 7.29 (1H, d, J=2.0 Hz), 7.20 (1H, dd, J=2.0 Hz, J2=8.4 Hz), 7.14 (1H, d, J=8.4 Hz), 5.41 (2H, s), 3.90 (2H, t, J=4.8 Hz), 3.86 (3H, s), 3.65 (2H, t, J=4.8 Hz), 2.43-2.50 (4H, m), 2.24 (3H, s); 19F NMR (DMSO-d6) d −59.5, −61.6; MS (ESI) 560 (MH+).

Provenance & Evidence