Triethylamine → SB-334867

Participants

Reaction Conditions

Reaction Steps

To 2-methyl-6-benzoxazole carboxylic acid (1.060 g) in toluene (111 ml) solution, triethylamine (0.867 ml) and N,N-dimethylformamide (22 ml) were added. To this mixture, diphenyl phosphoryl azide (1.65 ml) was added and stirred at 65° C. for an hour. The reaction mixture was cooled to room temperature, added with 4-amino-1,5-naphthyridine (0.878 g), and the resulting mixture was stirred at 65° C. for another 72 hours. The cooled mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium carbonate. The organic layer was dried with magnesium sulfate and the solvent was distilled away to obtain a crude product of 1-(2-methylbenzoxazole-6-yl)-3-[1,5]naphthyridine-4-yl urea for 0.797 g. The crude product was dissolved in ethyl acetate at 60° C., added with 4N-hydrogen chloride-ethyl acetate solution and stirred on ice. The precipitated hydrochloride was filtrated, air-dried at 60° C. to obtain 840 mg of the title compound (CAS No. 249889-64-3). The structure of the obtained title compound and results from NMR measurement were as follows.

Provenance & Evidence