Hydrogen Peroxide → HCID 72714944, compound

HRID 77357Notes

Reaction equation

HRID 77357 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([C:21]#[N:22])=[CH:19][CH:20]=[C:3]12.[OH-:23].[Li+].OO>O1CCCC1.O>[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([C:21]([NH2:22])=[O:23])=[CH:19][CH:20]=[C:3]12

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 727149431-Oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile

Product 1

HCID 72714944HCID 72714944, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile, (Example 2), (0.03 g, 98.9 82 mol), suspended in tetrahydrofuran (1 mL) was treated with a solution of lithium hydroxide (7.11 mg, 0.29 mmol) in water (500 μL) and 30 wt % aqueous hydrogen peroxide (40.4 μL, 0.39 mmol). The reaction was stirred at room temperature overnight. At this time, the reaction was concentrated in vacuo. The resulting residue was triturated with water. The resulting solid was collected by filtration and then dried in vacuo to afford 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid amide (20 mg, 61%) as light yellow solid. 1H NMR (methanol-d4) δ ppm 7.94 (d, J=1.5 Hz, 1H), 7.85-7.90 (m, 2H), 7.80-7.84 (m, 2H), 7.77 (s, 1H), 7.52 (d, J=0.8 Hz, 1H). LC-MS calcd. for C15H11F3N3O2 [(M+H)+] 322, obsd. 322.0.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. customThe resulting residue was triturated with water
  3. filtrationThe resulting solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e400e0c33f994c03b8fdf67939e4b997
Source dataset
uspto-grants-2014_09
Patent number
US08841299B2

Reaction notes

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