Triethylamine → 6-Methyl-2-phenyl-[1,2,4]triazolo[1,5-A]pyridin-7-amine

HRID 1802159Notes

Reaction equation

HRID 1802159 reaction equation
[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]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 677766756-Methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

Product 1

HCID 677751136-Methyl-2-phenyl-[1,2,4]triazolo[1,5-A]pyridin-7-amineYield 28.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 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+).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux
  3. custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record
ord-83e76c29bdf2479b87b89adf2fd29838
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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