Beta-Alanine → HCID 131731769, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2-{[3-(1,3-dioxolan-2-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide obtained in Step 1 as described above (290.00 mg; 0.72 mmol; 1.00 eq.), 2,4-thiazolidinedione (151.90 mg; 1.30 mmol; 1.80 eq.) and beta-alanine (115.55 mg; 1.30 mmol; 1.80 eq.) in AcOH (6.00 ml) are heated at 100° C. for 1 h30. Water is added and the precipitate is filtered and washed with Et2O, affording (62) as a yellow solid (35 mg; 9%). 1H NMR (DMSO-d6, 300 MHz) δ 1.92 (s, 3H), 2.14 (s, 3H), 2.50 (s, 3H), 6.98 (s, 1H), 7.22 (d, J=7.91 Hz, 1H), 7.50 (t, J=7.91 Hz, 1H), 7.73 (s, 1H), 7.80 (d, J=7.91 Hz, 1H), 7.85 (s, 1H), 10.59 (s, 1H), 11.92 (s, 1H), 12.06 (s, 1H), 12.60 (s, 1H). M−(ES): 456; M+(ESI): 458. HPLC, Rt: 3.52 min (purity: 93.0%).

Provenance & Evidence