* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With HATU; In N,N-dimethyl-formamide; at 20℃; for 168h;
Example 9 To a solution of 115 mg of 2-(3-fluoropiperidin-1-yl)-1,3-thiazole-4-carboxylic acid in 3 ml of DMF was added 110 mg of <strong>[76102-92-6]2-amino-N-pyridin-3-yl benzamide</strong>, and 228 mg of HATU, followed by stirring at room temperature for 7 days. To the reaction liquid was added water, and the precipitate was collected by filtration. This was purified by silica gel column chromatography (chloroform:methanol=99:1-30:1). This was heated and dissolved in 2-propanol, and then cooled to room temperature. The precipitate was collected by filtration to prepare 102 mg of 2-(3-fluoropiperidin-1-yl)-N-[2-(pyridin-3-ylcarbamoyl)phenyl]-1,3-thiazole-4-carboxamide.
Example 11 To a solution of 397 mg of 2-morpholin-4-yl-1,3-oxazole-4-carboxylic acid and 450 mul of 4-methylmorpholine in 10 ml of THF was added 260 mul of isobutyl chloroformate under ice-cooling, followed by stirring at room temperature for 30 minutes. Under ice-cooling, a solution of 426 mg of <strong>[76102-92-6]2-amino-N-pyridin-3-yl benzamide</strong> in 8 ml of THF was added thereto, followed by stirring at room temperature for 1 hour and at 60C overnight. The reaction mixture was concentrated under reduced pressure, water was then added thereto, and the precipitated solid was collected by filtration. This was suspended in ethanol, and 1.5 ml of a 4 M hydrogen chloride/EtOAc solution was added thereto, followed by stirring for 2 hours. The solid in the system was collected by filtration to prepare 250 mg of 2-morpholin-4-yl-N-[2-(pyridin-3-ylcarbamoyl)phenyl]-1,3-oxazole-4-carboxamide hydrochloride.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 60℃; for 72h;
Example 30 To a solution of 180 mg of 2-[methyl(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-4-carboxylic acid in 1.2 ml of DMF were added 117 mg of <strong>[76102-92-6]2-amino-N-pyridin-3-yl benzamide</strong>, 110 mg of WSC-HCl, and 100 mg of HOBt, followed by stirring at 60C for 3 days. To the reaction liquid was added an aqueous sodium hydrogen carbonate solution, and the resulting insoluble materials were collected by filtration. This was washed with acetonitrile to prepare 195 mg of 2-[methyl(tetrahydro-2H-pyran-4-ylmethyl)amino]-N-[2-(pyridin-3-ylcarbamoyl)phenyl]-1,3-thiazole-4-carboxamide.
With potassium hydroxide In ethanol for 12h; Reflux;
3.2. General procedure for the synthesis of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives 5a-o
General procedure: 2-Aminobenzamide derivatives 3a-o (1 mmol), carbon disulfide 4 (1.5 mmol), and KOH (2 mmol) in ethanol (15 mL) were heated under reflux for 12 h. After completion of the reaction (checked by TLC), reaction mixture was poured into water and the obtained product was filtered offand washed with water to give the pure 2-thioxo-2,3-dihydroquinazolin-4(1 H )-one derivatives 5a-o .
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;