[CH:1]([NH:4][C:5]1[C:6]2[N:7]([C:18]([O:21][CH3:22])=[N:19][N:20]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)([CH3:3])[CH3:2].Cl.[CH3:24][NH:25][O:26][CH3:27].ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:27][O:26][N:25]([CH3:24])[C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:18]([O:21][CH3:22])=[N:19][N:20]=[C:6]1[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[N:14]2)=[O:17]
A mixture of 4-isopropylamino-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid (127 mg), N,O-dimethylhydroxylamine hydrochloride (41 mg), 1-hydroxy-7-azabenzotriazole (57 mg), and EDC (81 mg) in DMF (2.0 mL) was stirred at 23° C. for 12 hrs. The solution was then diluted with EtOAc and washed sequentially with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride (2×) solutions. The organic layer was dried over sodium sulfate. The residue was purified by flash chromatography to afford 4-isopropylamino-1-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid-methoxy-methyl-amide. MS (M+H)+=345.7.
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