4-Ethylphenyl isocyanate → 2-[3-(4-Ethyl-phenyl)-ureidomethyl]-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide

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Reaction Steps

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chloro-phenyl)-ethyl]-amide (50 mg, 0.17 mmol) was dissolved in DMF (1 mL). 4-Ethyl phenylisocyanate (0.05 mL, 0.34 mmol) was added and the reaction mixture stirred at ambient temperature for 20 hours. The crude product was concentrated in vacuo. The product was purified by column chromatography (silica, 5% MeOH in DCM) to give a white solid (33.4 mg, 44%). 1H NMR (400 MHz, CD3OD): 8.07 (s, 1H), 7.26 (m, 4H), 7.19 (m, 2H), 7.11 (m, 2H), 4.66 (s, 2H), 3.60 (t, 2H), 2.90 (t, 2H), 2.58 (q, 2H), 1.20 (t, 3H); MS (ESI-LCMS) for C22H24C1N4O2S: 443 (MH+).

Provenance & Evidence