Water → HCID 11429076, compound

HRID 2217250Notes

Reaction equation

HRID 2217250 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:11]=[C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[CH:21]=2)=[N:14][CH:15]=1.O.C(Cl)Cl>CN(C=O)C>[NH2:9][C:10]1[N:11]=[C:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:13]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[CH:21]=2)=[N:14][C:15]=1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 691042475-(5-Amino-3-phenyl-2-pyrazinyl)-1-(1-methylethyl)-2(1H)-pyridinone

Product 1

HCID 11429076HCID 11429076, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-bath cooling, N-bromosuccinimide (1.83 g) was added to a solution of 5-(5-amino-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (3.0 g) in DMF (90 ml). The mixture was stirred at the same temperature for 2 hours. Water and CH2Cl2 were poured into the mixture and the organic layer was separated, washed with sat. aq. sodium thiosulfate solution, sat. aq. NaHCO3 solution, water, and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica-gel, toluene-EtOAc), recrystallized from EtOH, and dried in vacuo to give 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (3.0 g).

Workup

  1. temperatureUnder ice-bath cooling
  2. customthe organic layer was separated
  3. washwashed with sat. aq. sodium thiosulfate solution, sat. aq. NaHCO3 solution, water, and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography (silica-gel, toluene-EtOAc)
  7. customrecrystallized from EtOH
  8. customdried in vacuo

Sources & evidence

ORD record
ord-712460d9891d42df86b38616a0dafa70
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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