1,3-Benzodioxol-5-amine → 2-Ethoxycarbonyl-1-(3,4-methylenedioxyanilino)methyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one

HRID 1599422Notes

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.[CH2:26]1[O:35][C:34]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][C:28]=2[O: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][NH:31][C:30]1[CH:32]=[CH:33][C:34]2[O:35][CH2:26][O:27][C:28]=2[CH:29]=1)=[O:22])[CH3:25]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-bromomethyl-2-ethoxycarbonyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (Example 3) (2.1 g, 5.0 mmol) and 3,4-methylenedioxyaniline (1.5 g, 11 mmol) in acetonitrile (100 ml) was stirred at 80° C. for 3 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). The purified product was washed with acetone to afford 1.55 g (65%) of the title compound. M.p. >250° C.

Workup

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

Sources & evidence

ORD record: ord-231e0315841846068dbd4e20baa9b2ae
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

Loading…