1,2-Dichloroethane → 2-{[2-(4-Isopropyl-phenoxy)-acetylamino]-methyl}-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). EDC (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) where added and the mixture was stirred at ambient temperature for 10 minutes. (4-Isopropyl-phenoxy)-acetic acid (33 mg, 0.17 mmol) was added. The reaction mixture was stirred at ambient temperature for 18 hours. DI water was added and the mixture was extracted with ethyl acetate ×3. The combined organic layers were washed with 1 N hydrochloric acid ×2, 2 N sodium hydroxide ×2, 1 N sodium bicarbonate ×2, DI water ×2 and brine ×1, dried over sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography using silica (1:1 Ethyl acetate:Hexanes) to give the title compound as a semi-solid (16.8 mg, 21%). 1H NMR (400 MHz, d6-DMSO): 9.02 (t, 1H), 8.41 (t, 1H), 8.11 (s, 1H), 7.27 (m, 3H), 7.16 (m, 3H), 6.88 (d, 2H), 4.61 (d, 2H), 4.56 (s, 2H), 3.48 (q, 2H), 2.83 (m, 3H), 1.17 (d, 6H); MS (ESI-LCMS) for C24H27ClN3O3S: 472 (MH+).

Provenance & Evidence