HCID 5280153, compound → 5-[3-[2-(4-benzoylpiperazin-1-yl)-2-oxo-acetyl]-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl]pyrazine-2-carboxamide

HRID 899362Notes

Reaction equation

HRID 899362 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:42])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:29]4[N:30]=[CH:31][C:32]([C:35]([NH:37]C(C)(C)C)=[O:36])=[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>S(=O)(=O)(O)O.CO>[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:42])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([C:29]4[N:30]=[CH:31][C:32]([C:35]([NH2:37])=[O:36])=[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

Participants

4

Reactant 1

HCID 5280153HCID 5280153, compound

Product 1

HCID 52801705-[3-[2-(4-benzoylpiperazin-1-yl)-2-oxo-acetyl]-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl]pyrazine-2-carboxamideYield 5.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

The compound of Example 15, 1-benzoyl-4-[(4-methoxy-7-(2-(1,1-dimethylethylaminocarbonyl)-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (20 mg) was dissolved in 1 drop of concentrated sulfuric acid. After 30 minutes, the mixture was diluted with 2 mL of methanol. The resulting solution was injected into a Shimadzu automated preparative HPLC System and the HPLC purification afforded the compound of Example 55, 1-benzoyl-4-[(4-methoxy-7-(2-aminocarbonyl-pyrazin-5-yl)-6-azaindol-3-yl)-oxoacetyl]piperazine (1 mg); MS m/z: (M+H)+ Calc'd for C26H24N7O5: 514.78; found 514.22. HPLC retention time: 1.44 minutes (column B).

Workup

  1. customthe HPLC purification

Sources & evidence

ORD record
ord-7829669e9faa4a9ba0baea8d0b5287d0
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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