Homophthalic acid → 2-[(5-Benzylcarbamoyl-4-methylthiazol-2-ylcarbamoyl)methyl]benzoic acid

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Reaction Steps

2-Amino-4-methylthiazole-5-carboxylic acid benzylamide (0.25 g, 1.00 mmol) and homophthalic acid (0.18 g, 1.00 mmol) were melted together at 170° C. for 2 hours. A colorless solid formed after the melt was cooled to ambient temperature. The solid was washed with ether (50 mL) and then crystallized from ethyl acetate/methanol to afford the title compound in 60% yield; 1H NMR (DMSO-d6, 300 MHz) δ 12.37 (s, 1H), 8.48 (t, J=5.9 Hz, 1H), 7.88 (dd, J=1.4, 7.6 Hz, 1H), 7.50 (dt, J=1.4, 7.6 Hz, 1H), 7.40-7.15 (m, 7H), 4.34 (d, J=5.9 Hz, 2H), 4.14 (s, 2H), 2.45 (s, 3H); MS (ES+) m/z 410.5 (M+1).

Provenance & Evidence