Methyl p-toluenesulfonate → 2-(5-acetyl-2-ethylamino-phenylimino)-3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-thiazolidin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzyl-5-({N-[4-(2-methoxy-ethoxy)-phenyl]-methylamino}-methylene)-2-thioxothiazolidin-4-one (60 mg, 0.14 mmol) and methyl p-toluenesulfonate (54 mg, 0.29 mmol) in DMF (1.0 mL, anhyd) was heated at 130° C. After 2 h the reaction mixture was allowed to cool to ambient temperature, charged with 3′-amino-4′-ethylamino-acetophenone (50 mg, 0.28 mmol) and TEA (70 μL, 0.72 mmol), and then heated at 65° C. After 20 h the reaction mixture was cooled and chromatographed (HPLC-MS conditions) to yield the title product (7 mg) as a yellow solid. 1H-NMR (CDCl3): δ 7.82 (1H, s), 7.61 (1H, dd), 7.48 (1H, d), 7.27-7.40 (5H, m), 7.08 (2H, m), 6.90 (2H, m), 6.44 (1H, d), 5.09 (2H, s), 4.20 (1H, br s), 4.07 (2H, m), 3.73 (2H, m), 3.46 (3H, s), 3.44 (3H, s), 3.00 (2H, m), 2.43 (3H, s), 1.00 (3H, t); MS (ESI): 559 (MH+).

Provenance & Evidence