Bromoacetonitrile → (6-Methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetonitrile
Reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[NH:12][C:13](=[O:14])[N:5]([C:6]=23)[CH2:4][C:3]1=[O:15].[H-].[Na+].Br[CH2:19][C:20]#[N:21]>CN(C=O)C>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[N:12]([CH2:19][C:20]#[N:21])[C:13](=[O:14])[N:5]([C:6]=23)[CH2:4][C:3]1=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 6-methyl-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione (296 mg, 1.46 mmol, described in Intermediate 28) in DMF (5 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil; 78 mg, 1.96 mmol) and the resulting mixture was stirred for 5 min. Bromoacetonitrile (0.122 mL, 1.75 mmol) in was added dropwise and the reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h, then quenched with H2O (20 mL). The mixture was extracted with EtOAc (2×30 mL) and the combined organic extracts were washed with brine (10 mL), then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was partially purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, followed by trituration with CH2Cl2 to give the title compound. MS: m/z=243 (M+1).
Workup
- stirringwas stirred for 3 h
- customquenched with H2O (20 mL)
- extractionThe mixture was extracted with EtOAc (2×30 mL)
- washthe combined organic extracts were washed with brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was partially purified by silica gel chromatography
- washeluting with a gradient of CH2Cl2
Sources & evidence
- ORD record
- ord-43ce2e5159ba4df3b7091955139ce757
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968540B2
Reaction notes
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