Thiazole → 2-[4-(Pyrid-3-yloxymethyl)-2-phenylbenzoyl]4-ethylthiazole-5-carboxylic acid ethyl ester

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Reaction Steps

To a −12° C. solution in DMF (2 mL) of 2-amino-4-ethylthiazole-5-carboxylic acid methyl ester (80 mg, 0.40 mmol), prepared as described in J. Chem. Soc. Perkin 1, 1982, 154, was added lithium hexamethyldisilazide (1.0 M in THF, 0.76 mL, 0.76 mmol) and the resulting yellow solution was stirred for 30 minutes. In a separate flask 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid (101 mg, 0.33 mmol), prepared as in Example 228D and carbonyldiimidazole (60 mg, 0.37 mmol) were dissolved in THF and stirred for 1 hour. The resulting imidazolide solution was then added to the thiazole solution at −10° C. and the mixture was stirred for 30 minutes. The cold bath was then removed and stirring was continued for 30 minutes. The reaction mixture was quenched with saturated aqueous ammonium chloride and poured into water. The mixture was extracted twice with dichloromethane. The combine organic extracts were dried, filtered and concentrated. The solid residue was recrystallized from ethyl acetate-methanol to give 2-[4-(pyrid-3-yloxymethyl)-2-phenylbenzoyl]4-ethylthiazole-5-carboxylic acid ethyl ester (75 mg).

Provenance & Evidence