1-[(Diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one → 1-[(Ethoxyhydroxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:14]2[C:15]3[C:20]([NH:21][C:22](=[O:23])[C:13]2=[N:12][N:11]=1)=[CH:19][C:18]([C:24]([F:27])([F:26])[F:25])=[CH:17][CH:16]=3)([O:6]CC)=[O:5])[CH3:2]>C(O)C.[OH-].[Na+]>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:14]2[C:15]3[C:20]([NH:21][C:22](=[O:23])[C:13]2=[N:12][N:11]=1)=[CH:19][C:18]([C:24]([F:26])([F:27])[F:25])=[CH:17][CH:16]=3)([OH:6])=[O:5])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-[(diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one (750 mg, 1.85 mmol) in 20 ml of ethanol and 20 ml of 10% sodium hydroxide was stirred at room temperature for 1 h. The solvent was removed under reduced pressure, and the residue was dissolved in water and applied to an ion-exchange column (Amberlite IR-120, H+ -form) prewashed with 4M hydrochloric acid followed by deionized water. Elution with deionized water gave an acidic eluate, which was concentrated in vacuo to give 448 mg (65%) of the title compound, m.p. 276°-280° C. (from water); 1H-NMR (DMSO-d6): δ 1.16 (t, 3H), 3.98 (quint, 2H), 4.08 (d, 2H), 7.64 (d, 1H), 7.68 (s, 1H), 8.42 (d, 1H), 12.28 (s, 1H), MS: m/e 377 (MH+).
Workup
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was dissolved in water
- washElution with deionized water
- customgave an acidic eluate, which
- concentrationwas concentrated in vacuo
Sources & evidence
- ORD record
- ord-2d41864e4c05407db6bc346faa94c370
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05559106
Reaction notes
Loading…