Hydrogen Peroxide → HCID 54761809, compound

HRID 1630006Notes

Reaction equation

HRID 1630006 reaction equation
[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([F:25])=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]([C:17]#[N:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].OO.S([O-])([O-])(=[O:32])=S.[Na+].[Na+]>CO.O.C(OCC)(=O)C>[F:25][C:14]1[N:11]2[CH2:12][CH2:13][N:8]([C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]2=[C:16]([C:17]([NH2:18])=[O:32])[C:15]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 66585023HCID 66585023, compound

Product 1

HCID 54761809HCID 54761809, compoundYield 15.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.360 g (1.06 mmol) of N-tert-butyl-6-fluoro-8-cyano-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide in 4.2 ml of methanol is added 0.1 ml (1.1 mmol) of aqueous 35% sodium hydroxide solution and then 0.28 ml (3.2 mmol) of 35-volumes aqueous hydrogen peroxide solution. After stirring for 2 hours at 60° C., a further 0.05 ml (0.5 mmol) of 35-volumes aqueous hydrogen peroxide solution is added and the mixture is stirred for 16 hours at 60° C. After cooling, 0.25 g of sodium thiosulfate dissolved in 0.5 ml of water is added and the heterogeneous mixture is diluted with 75 ml of ethyl acetate. The organic phase is separated out, washed twice with 25 ml of water and then with 25 ml of saturated aqueous sodium chloride solution, after which it is dried over sodium sulfate. The solvent is evaporated off under reduced pressure to give a yellow oil, which is purified by chromatography on a column of silica gel, eluting with a mixture of 2 to 6% methanol in dichloromethane, to give 0.06 g of 6-fluoro-7-phenyl-N2-(tert-butyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a solid after triturating in diisopropyl ether, filtering off and drying.

Workup

  1. stirringthe mixture is stirred for 16 hours at 60° C
  2. temperatureAfter cooling
  3. additionis added
  4. customThe organic phase is separated out
  5. washwashed twice with 25 ml of water
  6. dry with materialwith 25 ml of saturated aqueous sodium chloride solution, after which it is dried over sodium sulfate
  7. customThe solvent is evaporated off under reduced pressure
  8. customto give a yellow oil, which
  9. customis purified by chromatography on a column of silica gel
  10. washeluting with a mixture of 2 to 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-0f557c9133af4c799d0ce9bc2d6a14b1
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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