HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-Bromo-N-(5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methyl 4-bromobenzoate | HCID 12081 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | 5-Methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine | HCID 23435881 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-Bromo-N-(5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide | HCID 10273828 | 15% |
Reaction Steps
To a solution of 24 mg (0.1 mmol) 5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl-amine in 1 ml dioxane was added 0.4 ml (0.4 mmol) of a 1 M solution of AlMe3 in toluene and allowed to stir for 1 h at room temperature. 86 mg (0.4 mmol) 4-bromo-phenyl carboxylic acid methyl ester in I ml dioxane was added and the mixture was stirred for 48 h at 90° C. 0.5 ml 1N HCl aq. was added and the mixture was evaporated to dryness. The residue was taken up in 1.5 ml formic acid and 0.5 ml methanol and subjected to reversed phase HPLC chromatography eluting with a water/acetonitrile gradient. Evaporation of the eluents yielded 6 mg (15%) of the title compound. MS m/e (%): 423.3 (M+H+, 100).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06693116B2 |
| Source dataset | uspto-grants-2004_02 |
| ORD ID | ord-ff8bd5bf6abf4716a704c2e934c7851d |
| Source note | uspto-grants-2004_02 |