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

HRID 1802201Notes

Reaction equation

HRID 1802201 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 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of hydroxylamine hydrochloride (20.0 g, 288 mmol) and N-ethyldiisopropylamine (30.1 ml, 173 mmol) in ethanol (367 ml) is stirred for a few minutes at room temperature and the mixture is added to 1-ethoxycarbonyl-3-(4-bromo-pyridin-2-yl)-thiourea (17.5 g, 57.5 mmol). The resulting mixture is refluxed for 1 day. The solvent is evaporated and 100 ml water is added to the residue. The suspension is stirred for 10 minutes, the solid is collected by filtration, washed with water and dried affording 7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (10.71 g, 87.4%) as a light yellow solid. Mp.: 190-2° C. MS: m/z=213.0, 215.0 (M+H+).

Workup

  1. temperatureThe resulting mixture is refluxed for 1 day
  2. customThe solvent is evaporated
  3. addition100 ml water is added to the residue
  4. stirringThe suspension is stirred for 10 minutes
  5. filtrationthe solid is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-afa48e4c5ab44df6a07a1212b8426b53
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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