1-Methylpiperazine → 3-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester

HRID 1697289Notes

Reaction equation

HRID 1697289 reaction equation
Cl[C:2]1[C:3](=[O:20])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C(#N)C>[Cl:8][C:6]1[N:7]=[C:2]([N:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)[C:3](=[O:20])[N:4]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 866632353-(3,5-Dichloro-2-oxo-1(2H)-pyrazinyl)-4-methyl-benzoic acid, methyl ester

Product 1

HCID 866632373-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-(3,5-dichloro-2-oxo-1(2H)-pyrazinyl)-4-methyl-benzoic acid, methyl ester, (Example 107a, 250 mg) in acetonitrile (5 mL) was added 1-methyl-piperazine (0.2 mL). After 12 h, the reaction mixture was concentrated in vacuo. The residue was diluted with dichloromethane, washed with sat. aqueous NaHCO3, dried (MgSO4), filtered and the solvent removed to afford the subtitle compound.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with sat. aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-892802930a9b45ec9c05ef3e30d34608
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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