Ethyl Acetate → HCID 69103269, compound

HRID 2217261Notes

Reaction equation

HRID 2217261 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.Cl.[CH3:26][NH:27][CH3:28].C(N(CC)C(C)C)(C)C.CCOC(C)=O>CN1C(=O)CCC1.O>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1[N:27]([CH3:28])[CH3:26]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 11429076HCID 11429076, compound

Product 1

HCID 69103269HCID 69103269, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg), dimethylamine hydrochloride (106 mg), N,N-diisopropylethylamine (201 mg) in NMP (1.0 ml) was heated at 150° C. with stirring for 65 hours. After cooling, EtOAc and water were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was recrystallized from MeOH-IPE and dried in vacuo to give 5-[5-amino-6-(dimethylamino)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (8 mg).

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was recrystallized from MeOH-IPE
  7. customdried in vacuo

Sources & evidence

ORD record
ord-78bd55dab02e4fa1b198d445a0a7e7b6
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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