Imidazole → HCID 17877358, compound

HRID 1599414Notes

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.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]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][C:27]1[NH:26][CH:30]=[CH:29][N:28]=1)=[O:22])[CH3:25]

Participants

Conditions

Temperature: 25 °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 imidazole (1.5 g, 22.0 mmol) in acetonitrile (200 ml) was stirred at 80° C. for 2 h and overnight at 25° C. The solvent was evaporated in vacuo and the residue submitted to flash chromatography on silica gel 60 eluting with dichloromethane/methanol (19:1) graduated to dichloromethane/methanol (1:9). The purified product was washed with water to give 2.0 g (49%) of the title compound. M.p. 187°-189° C.

Workup

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

Sources & evidence

ORD record: ord-71dea8c325dd4f95826f94af3702056f
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

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