Diisopropylethylamine → 5-Bromo-7-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine
Reaction equation
Cl.NO.C([N:7](C(C)C)CC)(C)C.[Br:13][C:14]1[N:19]=[C:18]([NH:20][C:21]([NH:23]C(OCC)=O)=S)[CH:17]=[C:16]([CH3:29])[CH:15]=1>C(O)C.CO>[Br:13][C:14]1[N:19]2[N:7]=[C:21]([NH2:23])[N:20]=[C:18]2[CH:17]=[C:16]([CH3:29])[CH:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a suspension of hydroxylamine hydrochloride (0.65 g, 9.27 mmol) in ethanol/methanol (1:1, 20 ml) was added diisopropylethylamine (0.97 ml, 5.56 mmol) and the mixture was stirred at room temp. (20° C.) for 1 h. 1-(6-Bromo-4-methyl-pyridin-2-yl)-3-carboethoxy-thiourea (0.59 g, 1.84 mmol) was added and the mixture slowly heated to reflux. Having refluxed overnight the mixture was allowed to cool and filtered to collect the precipitated solid. Further product was collected by evaporation in vacuo of the filtrate, addition of water and filtration. The combined solids were washed successively with water, ethanol/methanol and diethylether, then dried in vacuo to give the desired product. Yield 0.19 g, 45%. LCMS MI: 226.91+228.89, RT: 2.52 min, Method: 2
Workup
- temperaturethe mixture slowly heated to reflux
- temperatureHaving refluxed overnight the mixture
- temperatureto cool
- filtrationfiltered
- customto collect the precipitated solid
- filtrationFurther product was collected by evaporation in vacuo of the filtrate, addition of water and filtration
- washThe combined solids were washed successively with water, ethanol/methanol and diethylether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-4bb1e4c5aa6f4cffa9da3c16cfccfaf4
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431596B2
Reaction notes
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