(R)-1-Benzoyl-3-methylpiperazine → 1-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione

HRID 1783572Notes

Reaction equation

HRID 1783572 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12](=[O:16])[C:13]([O-:15])=O.[K+].[C:18]([N:26]1[CH2:31][CH2:30][NH:29][C@H:28]([CH3:32])[CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:18]([N:26]1[CH2:31][CH2:30][N:29]([C:13](=[O:15])[C:12]([C:5]2[C:4]3[C:8](=[C:9]([CH3:11])[CH:10]=[C:2]([Cl:1])[N:3]=3)[NH:7][CH:6]=2)=[O:16])[C@H:28]([CH3:32])[CH2:27]1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 7578227(R)-1-Benzoyl-3-methylpiperazineHCID 22893815Potassium (5-chloro-7-methyl-4-azaindol-3-yl)-oxoacetate

Product 1

HCID 54958371-[(2R)-4-benzoyl-2-methyl-piperazin-1-yl]-2-(5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)ethane-1,2-dione

Procedure

Precursor 5e, 1-benzoyl-3-(R)-methyl-4-[(5-chloro-7-methyl-4-azaindol-3-yl)-oxoacetyl]piperazine was prepared by the same method as Precursor 5a, starting from Potassium (5-chloro-7-methyl-4-azaindol-3-yl)-oxoacetate, Precursor 4f, and 1-benzoyl-3-(R)-methyl piperazine. MS m/z: (M+H)+ calcd for C22H22ClN4O3 425.24, found 425.04. HPLC retention time: 1.72 minutes (column B).

Sources & evidence

ORD record
ord-a0d40ebf93bf4947bb0c77ad323c0713
Source dataset
uspto-grants-2009_03
Patent number
US07501420B2

Reaction notes

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