Morpholine → HCID 69103534, compound

HRID 2217260Notes

Reaction equation

HRID 2217260 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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CN1C(=O)CCC1.CCOC(C)=O>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:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 11429076HCID 11429076, compound

Product 1

HCID 69103534HCID 69103534, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg), morpholine (113 mg), and NMP (1.0 ml) was heated at 150° C. with stirring for 1 day. 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, and the residue was recrystallized from MeOH-IPE and dried in vacuo to give 5-[5-amino-6-(4-morpholinyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (84 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-fc646ac706ff4999893553499ce78cdb
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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