2-CHLORO-3-NITROPYRAZINE

To m-chloroperbenzoic acid (8.0g, 0.46 mmol 85percent) in dichloromethane(100 mL)(cooled to -5°C) was added a solution of S, S-dimethyl-N-(2-pyrazinyl)sulfilimine (5.36 g, 0.028 mmol) in 30ml dichloromethane dorpwise at such a rate for 1 hour with the temperature not exceed 0°C, the reaction mixture was stirred for another 40min at 0°C, The solution of dimethyl sulfide in dichloromethane was added at 0°C. Filltered quickly to afford a orange clean solution .The solution was cooled to -78°C, then 0A mixture of 2-Chloro-3-nitro-pyrazine (0.5 g, 3 mmol) and [l-(4-Amino- phenyl)-cyclobutyl]-carbamic acid tert-butyl ester (0.98 g, 3.6 mmol) in dioxane (20mL) was added Et3N (2ml) in one portion. Then the reaction mixture was warmed to 70C for overnight. Cooled to room temperature and Concentrated to dryness to afford the residue, which was further purified by flash chromatography to afford { l-[4-(3-Nitro-pyrazin-2-ylamino)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester. (0.57 g, 50% yield). LC/MS (ESI+): 386[M+1]+, 388[M+3]+Step C 1-(3-Nitro-2-pyrazinyl)-4-(2-hydroxyethyl)piperazin-3-one A solution of 1-(3-Nitro-2-pyrazinyl)hexahydro-1H-1, 4-diazepin-5-one To a solution of hexahydro-1H-1, 4-diazepin-5-one (1.14 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in isopropanol (30 ml) cooled in an ice bath, was added over 30 minutes a solution of 1-(3-Nitro-2-pyrazinyl)piperazin-3-one A solution of Step B: Step B: Oxidation of the sulfilimine with MCPBA furnishes the nitro derivative.To m-chloroperbenzoic acid (8.0g, 0.46 mmol 85%) in dichloromethane(100 mL)(cooled to -5C) was added a solution of S, S-dimethyl-N-(2-pyrazinyl)sulfilimine (5.36 g, 0.028 mmol) in 30ml dichloromethane dorpwise at such a rate for 1 hour with the temperature not exceed 0C, the reaction mixture was stirred for another 40min at 0C, The solution of dimethyl sulfide in dichloromethane was added at 0C. Filltered quickly to afford a orange clean solution .The solution was cooled to -78C, then 03 was bubbled into the mixture until the orange solution was turned to be colorless. The resulting suspension was quenched with sodium dicarbonate solution and then extracted with dichloromethane for three times. The combined organic phase was concentrated to afford the crude product, which was further purified by flash chromatography to afford 2-Chloro-3-nitro-pyrazine. (0.5 g, yield: 7%).1HNMR (DMS0-

Molecular Weight:159.53
XLogP3:0.9
Hydrogen Bond Acceptor Count:4
Exact Mass:158.9835540
Monoisotopic Mass:158.9835540
Topological Polar Surface Area:71.6
Heavy Atom Count:10
Complexity:137
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes