Ammonium Chloride → 3-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

HRID 1697290Notes

Reaction equation

HRID 1697290 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11](OC)=[O:12])[CH:7]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.C([Mg]Cl)(C)C.[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([NH:30][CH:27]2[CH2:29][CH2:28]2)=[O:12])[CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69828CyclopropylamineHCID 866632373-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl esterHCID 178418918HCID 178418918, compound

Product 1

HCID 666864943-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[5-chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (Example 107b) in tetrahydrofuran (6 mL) under nitrogen was added cyclopropylamine (0.15 mL) followed by iso-propylmagnesium chloride (2M in tetrahydrofuran, 0.8 mL), portionwise. After 1 h, sat. aqueous NH4Cl was added and the mixture extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent) afforded the title compound (35 mg).

Workup

  1. extractionthe mixture extracted into ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by preparative HPLC (Gemini column, 0.1% ammonia:acetonitrile eluent)

Sources & evidence

ORD record
ord-71ca0ec315584243ad64586bfb45e02f
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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