Hydrogen Peroxide → HCID 54761997, compound

HRID 589846Notes

Reaction equation

HRID 589846 reaction equation
[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([Cl: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-:26].[Na+].OO>CO.CS(C)=O>[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([Cl:25])=[C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:16]([C:17]([NH2:18])=[O:26])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 66585082HCID 66585082, compound

Product 1

HCID 54761997HCID 54761997, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution at 65° C. of 40.0 g (112 mmol) of N-tert-butyl-6-chloro-8-cyano-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide in 400 ml of methanol and dimethyl sulfoxide (3:2) are added 10.1 ml (118 mmol) of aqueous 35% sodium hydroxide solution and then 19.8 ml (21.8 mmol) of 35-volumes aqueous hydrogen peroxide solution in 4 fractions every 15 minutes. After reaction for 30 minutes at 65° C., the mixture is cooled, partially concentrated under reduced pressure and taken up in dichloromethane. The organic phase is washed with water and is then dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give a yellow solid, which is crystallized from acetonitrile and then recrystallized from acetonitrile, to give 25.2 g of N2-(tert-butyl)-6-chloro-7-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide in the form of a white powder after filtering off and drying.

Workup

  1. customevery 15 minutes
  2. customAfter reaction for 30 minutes at 65° C.
  3. temperaturethe mixture is cooled
  4. concentrationpartially concentrated under reduced pressure
  5. washThe organic phase is washed with water
  6. dry with materialis then dried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure
  8. customto give a yellow solid, which
  9. customis crystallized from acetonitrile
  10. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-90c9dec10ca1486482e916a3037631c6
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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