Boron tribromide → N-[5-benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3-(3,4-dihydroxy-phenyl)-propanamide

Participants

Reaction Steps

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3-(3,4-dimethoxy-phenyl)-propanamide prepared in Example 68 and boron tribromide were used as starting materials, and the crude product was recrystallized with ethyl acetate to obtain a product as a white solid in a yield of 60.3%, mp: 94-95 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.61 (2H, t, J=7.00 Hz, CH2), 2.68 (2H, t, J=7.00 Hz, CH2), 4.17 (2H, s, CH2), 6.43 (1H, d, J=7.84 Hz, ArH), 6.59 (2H, t, J=7.84 Hz, CH2), 6.80 (2H, d, J=7.84 Hz, ArH), 7.18˜7.24 (3H, m, ArH), 7.32 (2H, t, J=7.28 Hz, CH2), 7.41 (2H, d, J=7.84 Hz, ArH), 8.65 (1H, s, OH), 8.74 (1H, s, OH), 9.59 (1H, s, OH), 12.06 (1H, s, CONH); EI-MS m/e (%): 446.1 (M+, 18), 282.1 (100), 205.1 (17); HREI-MS Calcd. for C25H22N2O4S: 446.1300. found: 446.1299.

Provenance & Evidence