Diisopropylethylamine → 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine
Reaction equation
Cl.NO.C([N:6](C(C)C)C(C)C)C.C(OC([NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=1)=S)=O)C>C(O)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]2[N:23]([N:6]=[C:19]([NH2:18])[N:21]=2)[CH:24]=1Participants
5
Conditions
- Temperature
- 25 °C
Procedure
A mixture of hydroxylamine hydrochloride (40.0 g, 575 mmol) and N-ethyldiisopropylamine (44.6 g, 60.3 ml, 345 mmol) in ethanol (734 ml) was stirred for a few minutes at 25° C., then the mixture was added to 1-ethoxycarbonyl-3-(5-bromo-pyridin-2-yl)-thiourea (35 g, 115 mmol) and the resulting mixture was refluxed for 1 day. The solvent was evaporated under reduced pressure and the white solid was treated with 400 ml water. The suspension was stirred for 1 hour, the solid was filtered off, washed with water 3 times and dried under reduced pressure, affording 6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (21 g, 85%) as white solid. Mp.: 185° C. MS: m/z=213.0/215.1 (M+H+).
Workup
- temperaturethe resulting mixture was refluxed for 1 day
- customThe solvent was evaporated under reduced pressure
- additionthe white solid was treated with 400 ml water
- stirringThe suspension was stirred for 1 hour
- filtrationthe solid was filtered off
- washwashed with water 3 times
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-38c989441e964fc685b2b681346a94b9
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227970B2
Reaction notes
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