1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one
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![1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220812/6600e6feca264f0aafa407eea31c2fdf.png "1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one")
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one
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CAS No:
6969-71-7
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Formula:
C6H5N3O
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Chemical Name:
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one
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Synonyms:
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one;s-Triazolo[4,3-a]pyridin-3-ol;3-Hydroxytriazolo[4,3-a]pyridine;NSC 68462;[1,2,4]Triazolo[4,3-a]pyridin-3-ol;2H,3H-[1,2,4]Triazolo[4,3-a]pyridin-3-one;2H-[1,2,4]Triazolo[4,3-a]pyridin-3-one;42240-05-1
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CAS No:
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Basic Attributes
135.12
135.12
607433
230-191-8
J5EWP6L1VA
68462
DTXSID70219980
2933990090
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (76.39%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 79 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Use and Manufacturing
[1, 2, 4]Triazolo[4, 3-a]pyridin-3-(2H)-one: A mixture of 2-chloropyridine (5.0 g, 44.03 mmol), semicarbazide hydrochloride (9.8 g, 88.06 mmol) and 2-ethoxyethanol (15 mL) was heated to reflux and treated with a solution of conc. sulfuric acid (0.1 mL) in 2-ethoxyethanol (1 mL). The resulting solution was maintained at reflux for 24 hours, cooled to about 60° C. and diluted with water (15 mL). The resulting solid was filtered and washed with water to yield the title product as a pale yellow solid (2.2 g, 51percent). m.p. 235-240° C.; Procedure 1. 1, 2, 4-Triazolo[4, 3-a]pyridin-3(2H)-one A mixture of crude CAP-004-05-A and urea (1.70 g, 27.50 mmol) was stirred at 130 oc for 3h. The resultant was purified by column chromatography on silica gel (ethylacetate/petroleum ether = 1/10-3/1) to give CAP-004-05 (0.13 g, 15 percent, two steps) as a pale white solid.At room temperature, [1, 2, 4] triazolo [4, 3-a] pyridine-3 (2H) -one (500mg, 3.70mmol), 1, 2-bromomethane (0.73mL, 8.50mmol) and DMF (10.0 mL), then NaH (125 mg) was added, and the reaction mixture was stirred at room temperature for 6 h.The reaction was quenched by adding water (30 mL), and then extracted with EA (30 mL × 2). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. Petroleum ether (10 mL) was added to it, stirred for 30 min, filtered, the filtrate was collected, and dried in vacuo to give the title compound as a red solid (490 mg, 2.02 mmol, 54.70%).135mg, 1 mmol and potassium carbonate (152mg, 1.1 mmol)were added into DMF (5 mL), 1-bromo-4-chlorobutane (5mmol) was dripped under the ice bath, and the mixture was stirred at roomtemperature overnight. The reaction liquid was poured into ice water and extractedwith EA. The organic layer was washed with water and brine, dried overanhydrous sodium sulfate, concentrated under reduced pressure to obtain crudeproduct. The crude product is slurried in PE, filtered and dried to obtain a lightyellow solid (155 mg, 69%).
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one was used to prepare a congener of Trazodone (T718500) which was found to be a potent and selective inhibitor of synaptosomal uptake of 5-hydroxytryptamine.
Computed Properties
Molecular Weight:135.12
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:135.043261791
Monoisotopic Mass:135.043261791
Topological Polar Surface Area:44.7
Heavy Atom Count:10
Complexity:264
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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