Methyl iodide → HCID 15958728, compound

HRID 899370Notes

Reaction equation

HRID 899370 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:36])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:29]4[N:30]=[CH:31][C:32]([OH:35])=[N:33][CH:34]=4)[N:23]=[CH:24][C:25]=3[O:27][CH3:28])[NH:20][CH:19]=2)=[O:17])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:39]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:36])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:29]4[N:30]=[CH:31][C:32](=[O:35])[N:33]([CH3:39])[CH:34]=4)[N:23]=[CH:24][C:25]=3[O:27][CH3:28])[NH:20][CH:19]=2)=[O:17])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178493712HCID 178493712, compound

Product 1

HCID 15958728HCID 15958728, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(benzoyl)-4-[(4-methoxy-7-(2-hydroxyl-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (6 mg), MeI (5 mg) and K2CO3 (4 mg) were dissolved in acetone (5 ml). The reaction was stirred for four hours at room temperature. After solid was filtered away, the mother liquid was concentrated to give a residue which was purified using a Shimadzu automated preparative HPLC System to provide 3.0 mg of the desired compound, 1-(benzoyl)-4-[(4-methoxy-7-(1-methylpyrazin-2-on-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine. MS m/z: (M+H)+ Calc'd for C26H25N6O5: 501.19; found 501.14. HPLC retention time: 1.08 minutes (column G).

Workup

  1. filtrationAfter solid was filtered away
  2. concentrationthe mother liquid was concentrated
  3. customto give a residue which
  4. customwas purified

Sources & evidence

ORD record
ord-a6543b4d02f64406b640001f57f67147
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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