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

HRID 1054949Notes

Reaction equation

HRID 1054949 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]([Cl:28])[CH:25]=[CH:24][N:23]=1)=S)=O)C>C(O)C>[Cl: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 90016559HCID 90016559, compound

Product 1

HCID 468640707-Chloro[1,2,4]triazolo[1,5-a]pyridin-2-amineYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of hydroxylamine hydrochloride (5.35 g, 77.0 mmol, Eq: 5) and N-ethyldiisopropylamine (5.97 g, 8.07 ml, 46.2 mmol, Eq: 3) in ethanol (80 ml) was stirred for a few minutes at 25° C., then the mixture was added to 1-ethoxycarbonyl-3-(4-chloro-pyridin-2-yl)-thiourea (4.0 g, 15.4 mmol, Eq: 1.00) and the resulting mixture was refluxed for 2.5 days (over the weekend). The crude material was applied on SiO2 and purified by flash chromatography over a 20 g SiO2 column using ethyl acetate 100% as eluent affording 7-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (2.03 g/78.2%) as a white solid. MS: m/e=169.1 (M+H+), mp: 189-190° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 2.5 days (over the weekend)
  2. custompurified by flash chromatography over a 20 g SiO2 column

Sources & evidence

ORD record
ord-c5835de3d5c64556823ea319ce948df0
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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