2-Methylimidazole → 2-Ethoxycarbonyl-1-(2-methyl-1-imidazolyl)methyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one

HRID 1599416Notes

Reaction equation

Br[CH2:2][C:3]1[N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[C:6]2=[N:5][C:4]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=3.[CH3:26][C:27]1[NH:28][CH:29]=[CH:30][N:31]=1>C(#N)C>[CH2:24]([O:23][C:21]([C:4]1[N:5]=[C:6]2[C:15](=[O:16])[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)[N:7]2[C:3]=1[CH2:2][N:28]1[CH:29]=[CH:30][N:31]=[C:27]1[CH3:26])=[O:22])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-bromomethyl-2-ethoxycarbonyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (Example 3) (4.18 g, 10.0 mmol) and 2-methylimidazole (1.8 g, 22.0 mmol) in acetonitrile (200 ml) was stirred at 80° C. for 4 h. The solvent was evaporated in vacuo and the residue submitted to flash chromatography on silica gel 60 eluting with dichloromethane/methanol (19:1). The purified product was washed with water to give 2.6 g (62%) of the title compound. M.p. >250° C.

Workup

customThe solvent was evaporated in vacuo
washThe purified product was washed with water

Sources & evidence

ORD record: ord-85efc35038d04364af32dbc149f5a5ac
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

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