Diisopropylethylamine → 7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 1802147Notes

Reaction equation

HRID 1802147 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]=[C:26]([Br:28])[CH:25]=[CH:24][N:23]=1)=S)=O)C>C(O)C>[Br:28][C:26]1[CH:25]=[CH:24][N:23]2[N:6]=[C:19]([NH2:18])[N:21]=[C:22]2[CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57643101HCID 57643101, compound

Product 1

HCID 545940257-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amineYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hydroxylamine hydrochloride (20.7 g, 298 mmol) and N-ethyldiisopropylamine (23.1 g, 31.2 ml, 179 mmol) in ethanol (380 ml) is stirred for a few minutes at 25° C. The mixture is then added to 1-ethoxycarbonyl-3-(4-bromo-pyridin-2-yl)-thiourea (18.13 g, 59.6 mmol) and the resulting mixture is refluxed for 1 day. The solvent is evaporated to dryness and the residue triturated for 10 minutes with water (100 ml). The solid is collected by filtration, washed with water and dried affording 7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (10 g, 78.8%) as a light yellow solid. mp.: 190-2° C. MS: m/z=212.9, 215.0 (M+H+).

Workup

  1. temperaturethe resulting mixture is refluxed for 1 day
  2. customThe solvent is evaporated to dryness
  3. customthe residue triturated for 10 minutes with water (100 ml)
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-72c05c280aa84b5a877b79110c571ebc
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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