2-(Benzenesulfonyl)-3-phenyloxaziridine → 2-Methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277121Notes

Reaction equation

HRID 277121 reaction equation
[CH3:1][S:2][C:3]1[N:18]=[C:6]2[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[C:10]([NH2:11])[N:5]2[N:4]=1.C1(C2[O:27]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.C(OC(=O)C)C.CO>ClCCl>[CH3:1][S:2]([C:3]1[N:18]=[C:6]2[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[C:10]([NH2:11])[N:5]2[N:4]=1)=[O:27]

Participants

5

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 183136312-Methylsulfanyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineHCID 21584119Ethylacetate methanol

Product 1

HCID 226297032-Methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8.66 g (0.034 mol) 2-Methylsulfanyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine in 850 ml dichloromethane were oxidised with a solution of 17.6 g (0.067 mol) 3-phenyl-2-(phenylsulfonyl)oxaziridine in 150 ml dichloromethane overnight. Chromatography on aluminiumoxide (dichloromethane/ methanol 97:3) and on silicagel (ethylacetate/methanol 9:1) yielded 5.2 g (57%) 2-methanesulfinyl-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine, MS m/e (%):274 (M+H+,100).

Sources & evidence

ORD record
ord-543d754f555246b08eea5c0c9bcad15b
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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