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Thiazole-5-carboxylic acid (Example 69) was prepared according to the method described in WO97/14687, and 5-methyl-thiazole-2-carboxylic acid (Example 61) was prepared analogously. 2-Methyl-thiazole-4-carboxylic acid (Example 74) was prepared by analogy to the method of W. R.
N-(2,6-dimethoxyphenyl)thiazole-5-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
An ice-cooled solution of thiazole-5-carboxylic acid (Asta Tech Inc., 927 mg, 7.2 mmol) in DMF (20 mL) was treated with TEA (3.0 mL, 21.5 mmol) followed by HATU (3.4 g, 9.0 mmol). After 3 min, <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (Amfinecom Inc., 1.1 g, 7.2 mmol) was added, and the resulting brown solution was warmed to RT and stirred for 60 min. Next, the reaction was partitioned between brine (125 mL) and EtOAc (2X). The combined organic layers were washed with water (1X) and brine (1X), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 10-100% EtOAc in hexanes) to provide 397.01 (1.79 g, 94% yield) as a light orange solid. LCMS-ESI (pos.) m/z: 265.2 (M+H)+.
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