Hydrochloric Acid → 4-({[2'-(Acetylamino)-4'-methyl-4,5'-bi-1,3-thiazol-2-yl]carbonyl}amino)-2-hydroxybenzoic acid

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Reaction Steps

2′-(acetylamino)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)-4′-methyl-4,5′-bi-1,3-thiazole-2-carboxamide (150 mg; 0.33 mmol; 1 eq.) is dissolved in THF (6 ml). Sodium hydroxide (0.82 ml; 5 M; 4.09 mmol; 12.50 eq.) is added and the mixture is stirred at rt for 10 days. Hydrogen chloride (0.82 ml; 5 M; 4.09 mmol; 12.50 eq.) is added and the solvents are evaporated. The resulting crude product is purified by preparative HPLC. To remove the TFA, the compound is dissolved in THF and an excess of POL-Trisamine (Argonault) is added. The solution is filtrated and evaporated, affording Compound (31)(54 mg; 39%). Potassium salt of 4-({[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]carbonyl}amino)-2-hydroxybenzoic acid, Compound (31), is prepared by dissolving the parent compound (54 mg, 0.129 mmol) in THF (2 ml) and water (2 ml). Potassium hydroxide 0.5N solution (258 μl, 1 eq) is added. The mixture is stirred 10 min at rt, filtered through cotton and is lyophilized. Potassium salt of compound (31) is isolated as a yellow solid (21.6 mg; 36%).

Provenance & Evidence