6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

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6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine manufacturers

6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Basic information
Product Name:6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine
Synonyms:6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine;2-Amino-6-chloro-[1,2,4]triazolo[1,5-a]pyridine;1,2,4]Triazolo[1,5-a]pyridin-2-amine, 6-chloro-
CAS:1239647-60-9
MF:C6H5ClN4
MW:168.58
EINECS:
Product Categories:
Mol File:1239647-60-9.mol
6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Structure
6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceWhite to light yellow Solid
Safety Information
HS Code 2933998090
MSDS Information
6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Usage And Synthesis
Synthesis
ethyl [(5-chloro-2-pyridinyl)amino]carbothioylcarbamate

78852-50-3

6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

1239647-60-9

General procedure for the synthesis of 6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine from ethyl N-[[(5-chloro-2-pyridinyl)amino]thiomethyl]carbamate: Hydroxylammonium chloride (4.4 g) was suspended in methanol (35 mL), and ethanol (35 mL) and Hünig's base (10.2 mL) were added sequentially at room temperature. The reaction mixture was heated to 60 °C, N-[[(5-chloro-2-pyridinyl)amino]thiomethyl]carbamic acid ethyl ester (4.4 g) was added in batches and the reaction was stirred at 60 °C for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the solid was precipitated by addition of water (150 mL). The solid product was collected by filtration, washed with water and dried under reduced pressure to afford 6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (2.0 g). The product was characterized by 1H-NMR (300 MHz, DMSO-d6): δ[ppm] = 6.09 (2H), 7.28-7.37 (1H), 7.39-7.49 (1H), 8.84 (1H).

References[1] Patent: WO2014/9219, 2014, A1. Location in patent: Page/Page column 111
[2] Patent: WO2014/195276, 2014, A1. Location in patent: Page/Page column 113-114
[3] Patent: WO2014/198647, 2014, A2. Location in patent: Page/Page column 79
[4] Patent: US2015/148542, 2015, A1. Location in patent: Paragraph 0531; 0532; 0533; 0534
6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Preparation Products And Raw materials
Raw materialsethyl [(5-chloro-2-pyridinyl)amino]carbothioylcarbamate-->2-Amino-5-chloropyridine-->Methanol-->Ethanol-->N,N-Diisopropylethylamine-->Hydroxylamine hydrochloride
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