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Ammonia → HCID 67363450, compound

HRID 245771
Notes
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Reaction equation

HRID 245771 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][CH:4]([C:8]([NH:10][CH2:11][C:12]2[C:17]([CH3:18])=[N:16][CH:15]=[CH:14][N:13]=2)=O)[CH2:3]1.N.C(OCC)(=O)C.CO>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CO>[CH3:1][N:2]1[CH2:3][CH:4]([C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:17]([CH3:18])[C:12]3=[CH:11][N:10]=2)[CH2:5][C:6]1=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 21584119Ethylacetate methanolHCID 67362972HCID 67362972, compound

Product 1

HCID 67363450HCID 67363450, compoundYield 108.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 86584057
Phosphorus Pentoxide-Methanesulfonic Acid
Solvent

Conditions

Temperature
60 °C

Procedure

1-Methyl-N-((3-methylpyrazin-2-yl)methyl)-5-oxopyrrolidine-3-carboxamide (330 mg, 1.329 mmol) was dissolved in Eaton's reagent (2 ml) and the reaction mixture was stirred at 60° C. for 18 hour. Then the reaction mixture was poured into an ice-bath and basified with 7N ammonia in methanol (20 ml). The resulting mixture was extrated with chloroform/iso-propanol (9/1) five times. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue (280 mg) was stripped with toluene twice and with dichloromethane twice. An additional crop (53 mg) was obtained by extraction of the water layer with chloroform/iso-propanol (9/1) twice and drying and concentrating as described before. In total 333 mg of crude 1-methyl-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)pyrrolidin-2-one was obtained which was used in the next reaction without further purification.

Workup

  1. additionThen the reaction mixture was poured into an ice-bath
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customAn additional crop (53 mg) was obtained by extraction of the water layer with chloroform/iso-propanol (9/1) twice
  5. customdrying
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-318bd86d40564d8cbb1e31a6f71149c2
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658794B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes