Diisopropylethylamine → 1-(4-benzoylpiperazin-1-yl)-2-[7-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]ethane-1,2-dione

HRID 899365Notes

Reaction equation

HRID 899365 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][N:12]=[C:13]3[C:17]=2[NH:16][CH:15]=[C:14]3[C:18](=[O:22])[C:19]([O-])=[O:20])=[CH:5][CH:4]=1.[K+].[C:24]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OP(ON1C(=O)C2C=CC=CC=2N=N1)(OCC)=O)C.CCN(C(C)C)C(C)C>CN(C=O)C>[C:24]([N:32]1[CH2:37][CH2:36][N:35]([C:19](=[O:20])[C:18]([C:14]2[C:13]3[C:17](=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH:10]=[CH:11][N:12]=3)[NH:16][CH:15]=2)=[O:22])[CH2:34][CH2:33]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7626541-BenzoylpiperazineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 59693981Potassium 7-(4-methoxyphenyl)-4-azaindole-3-glyoxylate

Product 1

HCID 52802241-(4-benzoylpiperazin-1-yl)-2-[7-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-3-yl]ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure for the preparation of Examples 65-67 is the same as that described previously for the preparation of Precursor 5a and is as follows: Potassium 7-(4-methoxyphenyl)-4-azaindole-3-glyoxylate, Precursor 4c (147 mg, 0.44 mmol), an appropriate 1-benzoylpiperazine derivative (0.44 mmol), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) (101 mg, 0.44 mol) and Hunig's Base (0.5 mL) were combined in 5 mL of DMF. The mixture was stirred at rt for 8 h. DMF was removed via evaporation at reduced pressure and the residue was purified using a Shimadzu automated preparative HPLC System to give the corresponding 1-benzoyl-4-[(7-(4-methoxyphenyl)-4-azaindol-3-yl)-oxoacetyl]-piperazine derivative.

Workup

  1. customThe procedure for the preparation of Examples 65-67
  2. customDMF was removed via evaporation at reduced pressure
  3. customthe residue was purified

Sources & evidence

ORD record
ord-9571b2bd2593415183ed644ea45a1f78
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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