Triethylamine → 8-Methyl-2-phenyl-[1,2,4]triazolo[1,5-A]pyridin-7-amine

HRID 1802156Notes

Reaction equation

HRID 1802156 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1C(O)=O.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]2[N:4]([N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[NH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 677768818-Methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid

Product 1

HCID 677757028-Methyl-2-phenyl-[1,2,4]triazolo[1,5-A]pyridin-7-amineYield 25.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a suspension of 8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylic acid (710 mg, 2.81 mmol) and triethylamine (1.17 ml, 8.42 mmol) in tert-butanol (20 ml) is added diphenyl phosphorazidate (909 μl, 4.21 mmol) at 25° C. After the addition the white suspension is refluxed for 24 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% and then ethyl acetate/methanol 10% as eluent affording 8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (160 mg, 25.4%) as a white solid. mp.: 213-5° C. MS: m/z=225.2 (M+H+).

Workup

  1. additionAfter the addition the white suspension
  2. temperatureis refluxed for 24 hours
  3. custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record
ord-23403543f9c94721aabbb461d2bccc5b
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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