Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:5]2.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[NH:20][NH2:21]>CO.OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[N:21][NH:20][C:19]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:5]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 1.5 g of 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one (prepared by a procedure analogous to Example 1, Step B) and 0.63 g of ethyl carbazate in 20 ml of methanol was added 1 drop of conc. H2SO4 and the reaction was refluxed under nitrogen overnight. The reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO3, the aqueous extracts were washed with ethyl acetate and the combined organic extracts were dried over MgSO4. Concentration of the organic extract afforded 1.9 g of a yellow oil, which was triturated with ether to afford 1.27 g of a white solid, m.p. 139°-141° C. 1H NMR (CDCl3) δ 1.26 (t, 3H), 2.91 (dd, 1H), 3.70 (dd, 1H), 4.2 (m, 3H), 6.9-7.3 (m, 6H), 7.52 (bs, 1H ), 7.93 (dd, 1H ).
Workup
- temperaturethe reaction was refluxed under nitrogen overnight
- customThe reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO3
- washthe aqueous extracts were washed with ethyl acetate
- dry with materialthe combined organic extracts were dried over MgSO4
- extractionConcentration of the organic extract
Sources & evidence
- ORD record
- ord-9e4ec8be14c54895b8dce5e69857e66d
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428027
Linked notes
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