Pyridine → 2-{[2-(4-Trifluoromethoxyphenoxy)-acetylamino]-methyl}thiazole-4-carboxylic acid [2-(3-chlorophenyl)-ethyl]amide

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Reaction Steps

2-Aminomethyl-thiazole-4-carboxylic acid [2-(3-chlorophenyl)ethyl]amide (0.54 g, 1.8 mmol) was dissolved in methylene chloride (15 mL). (4-Trifluoromethoxyphenoxy)-acetyl chloride (0.47 g, 1.8 mmol) was added followed by pyridine (0.3 mL, 4 mmol) and DMAP (0.02 g, 0.1 mmol). The mixture was stirred for 12 hours. Saturated, aqueous NH4Cl was added and the mixture was extracted with methylene chloride ×3. The combined organic extracts were washed with 1N HCl, saturated, aqueous NaHCO3, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The material was purified by recrystallization from ethanol/diethyl ether to afford the title compound (0.65 g, 68% from the Boc protected amine): 1H NMR (400 MHz, d6-DMSO): 9.08 (t, 1H), 8.40 (t, 1H), 8.10 (s, 1H), 7.27 (m, 5H), 7.17 (d, 1H), 7.06 (d, 2H), 4.65 (s, 2H), 4.62 (d, 2H), 3.48 (m, 2H), 2.84 (t, 2H); MS (ESI-LCMS) for C22H20ClF3N3O4S: 514 (MH+).

Provenance & Evidence