Bromotrimethylsilane → 1-Phosphonomethyl-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

HRID 744026Notes

Reaction equation

Br[Si](C)(C)C.C([O:8][P:9]([CH2:14][C:15]1[N:19]2[C:20]3[C:25]([NH:26][C:27](=[O:28])[C:18]2=[N:17][N:16]=1)=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][CH:21]=3)([O:11]CC)=[O:10])C>C(#N)C>[P:9]([CH2:14][C:15]1[N:19]2[C:20]3[C:25]([NH:26][C:27](=[O:28])[C:18]2=[N:17][N:16]=1)=[CH:24][C:23]([C:29]([F:31])([F:30])[F:32])=[CH:22][CH:21]=3)([OH:10])([OH:11])=[O:8]

Participants

Conditions

Temperature: 40 °C

Procedure

Bromotrimethylsilane (0.75 ml, 5.8 mmol) was added to a suspension of 1-[(diethoxyphosphoryl)methyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one (315 mg, 0.78 mmol) in 15 ml of dry acetonitrile in a flame-dried flask under nitrogen, and the resulting solution was stirred overnight at 40° C. After evaporation to dryness, the residue was stirred with 25 ml of water for 1 h. Then the water was removed under reduced pressure by azeotropic distillation with 1-propanol, and the residue was crystallized by trituration with a mixture of ether and ethanol followed by light petroleum. The solid was recrystallized from water, and dried in vacuo to give 189 mg (70%) of the title compound, m.p.>290° C. dec. (DSC); 1H-NMR (DMSO-d6): δ 3.96 (d, 2H), 7.64 (d, 1H), 7.69 (s, 1H), 8.47 (d, 1H), 12.28 (s, 1H); IR (KBr): 1712 cm-1 ; MS (FAB): m/e 349 (MH+).

Workup

customAfter evaporation to dryness
stirringthe residue was stirred with 25 ml of water for 1 h
customThen the water was removed under reduced pressure by azeotropic distillation with 1-propanol
customthe residue was crystallized by trituration with a mixture of ether and ethanol
customThe solid was recrystallized from water
customdried in vacuo

Sources & evidence

ORD record: ord-4826525391004de588074152ecf4e42a
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559106

Reaction notes

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