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(116c) A 2 N aqueous solution of KOH (3.5 mL, 5 eq) was added to ethyl thiazole-2-carboxylate (213 mg, 1.355 mmol) in ethanol (3 mL). After 2 h at room temperature, the mixture was acidified with 2 N HCl (3.5 mL). Upon sitting overnight, a needle crystal was formed, which was collected by filtration to give thiazole-2-carboxylic acid (43.3 mg, 25percent).
Step 3 : Thiazole-2-carboxylic acid; A solution of ethyl thiazole-2-carboxylate (1.46g; 9.29mmol), obtained using a literature method (HeIv. Chim Acta 1945, 28, p. 924), in EtOH (10 ml) was placed in a sealable vessel and treated with KOH (3.07g; 46.4mmol). The vessel was sealed and heated at 120°C for 30min. After cooling, the solution was poured into water (50mL) and the pH adjusted to 4.0 with con. HCl. The now turbid mixture was extracted with iPrOAc (50mL), dried over magnesium sulfate, filtered and evaporated to a brown oil. The oil was dissolved in CH2Cl2 and filtered, then evaporated to afford the title compound as a brown pasty solid.
Step 3: Thiazole-2-carboxylic acid; A solution of ethyl thiazole-2 -carboxylate (1.46g; 9.29mmol), obtained using a literature method (HeIv. Chim Acta 1945, 28, p. 924), in EtOH (10 ml) was placed in a sealable vessel and treated with KOH (3.07g; 46.4mmol). The vessel was sealed and heated at 1200C for 30min. After cooling, the solution was poured into water (5OmL) and the pH adjusted to 4.0 with con. HCl. The now turbid mixture was extracted with iPrOAc (5OmL), dried over magnesium sulfate, filtered and evaporated to a brown oil. The oil was dissolved in CH2Cl2 and filtered, then evaporated to afford the title compound as a brown pasty solid.
Example 226; (R)-N-(2-(l-(4-fluorophenyl)-5-methyl-4,5-dihydro-lH-indazol-5- yl)ethyl)thiazole-2-carboxamide; [00447] (226a) To an ethanol (3 mL) solution of thiazole-2-carboxylic acid ethyl ester (213 mg, 1.355 mmol) was added aqueous KOH (2 M, 3.5 mL). The mixture EPO <DP n="130"/>was stirred at room temperature for 2 h then concentrated, acidified with aqueous HCl (2 M, 3 mL). The resulting white needle crystal (43 mg) was collected from the solution by filtration.
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