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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;
A mixture of 2-tert-butoxycarbonylamino-pentanoic acid (5.432g, 25 mmol.), 5-tert-butyl-[1,3,4]thiadiazol-2-ylamine (3.925g, 25 mmol), HBOT (3.540g, 26.25 mmol), EDC HCl (5.73g, 30 mmol.) and triethylamine (14 ml) in methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound (9.2671 g), LC-MS M+1=357.2.
With triethylamine; In dichloromethane; at 0 - 20℃;
To a solution of 5-tert-butyl-1,3,4-thiadiazol-2-amine (1.57 g, 10 mmol) and <strong>[207981-46-2]2-fluoro-5-(trifluoromethyl)benzoyl chloride</strong> (2.27 g, 10 mmol) in CH2Cl2 (45 mL) at 0 C. was added dropwise triethylamine (1.7 mL, 12 mmol) and the reaction was allowed to warm to ambient temperature and stirred for 12 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure to afford 3.2 g of the title compound. MS (DCI/NH3) m/z 348 (M+H)
With triethylamine; In dichloromethane; at 20℃;
Example 3A N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-fluoro-5-(trifluoromethyl)benzamide To a solution of 5-tert-butyl-1,3,4-thiadiazol-2-amine (1.57 g, 10 mmol) and <strong>[207981-46-2]2-fluoro-5-(trifluoromethyl)benzoyl chloride</strong> (2.27 g, 10 mmol) in CH2Cl2 (45 mL) at 0 C. was added triethylamine (1.7 mL, 12 mmol) dropwise and the reaction mixture was allowed to warm to ambient temperature for 12 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure to afford 3.2 g of the title compound. MS (DCI/NH3) m/z 348 (M+H)+.
With triethylamine; In dichloromethane; at 0 - 20℃;
Example 45A N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-fluoro-5-(trifluoromethyl)benzamide To a solution of 5-tert-butyl-1,3,4-thiadiazol-2-amine (1.57 g, 10 mmol) and <strong>[207981-46-2]2-fluoro-5-(trifluoromethyl)benzoyl chloride</strong> (2.27 g, 10 mmol) in CH2Cl2 (45 mL) at 0 C. was added dropwise triethylamine (1.7 mL, 12 mmol) and the reaction mixture was allowed to warm to ambient temperature for 12 h. The mixture was then washed with water, brine, dried with MgSO4, and concentrated under reduced pressure to afford 3.2 g of the title compound. MS (DCI/NH3) m/z 348 (M+H)+.
With triethylamine; In dichloromethane; at 0 - 20℃;
To a solution of 5-tert-butyl-1,3,4-thiadiazol-2-amine (1.57 g, 10 mmol) and <strong>[207981-46-2]2-fluoro-5-(trifluoromethyl)benzoyl chloride</strong> (2.27 g, 10 mmol) in CH2Cl2 (45 mL) at 0 C. was added dropwise triethylamine (1.7 mL, 12 mmol) and the reaction was allowed to warm to ambient temperature and stirred for 12 hours. The mixture was then washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure to afford 3.2 g of the title compound. MS (DCI/NH3) m/z 348 (M+H)
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