[CH3:1][C:2]1[C:3](C(O)=O)=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C([N:22](CC)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1>C(O)(C)(C)C>[CH3:1][C:2]1[C:3]([NH2:22])=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1To a suspension of 6-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (172 mg, 679 μmol) and triethylamine (206 mg, 284 μl, 2.04 mmol) in tert-butanol (10 ml) is added at 25° C. diphenyl phosphorazidate (220 μl, 1.02 mmol). The resulting mixture is heated to reflux and stirred for 18 hours. The crude material is loaded on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 10-100% as eluent affording 6-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (43 mg, 28%) as an off-white solid. mp.: >250° C. MS: m/z=225.3 (M+H+). The hydrochloride can be prepared by stirring in tetrahydrofurane/6N hydrochloric acid in diethylether (1:6) for 2 hours and final evaporation to dryness. Light brown solid (quant.). MS: m/z=225.3 (M+H+).
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