1-Hydroxybenzotriazole → 2-Methyl-5-(4-{[3-(1H-pyrazol-1-yl)phenyl]acetyl}-1-piperazinyl)quinoline

HRID 734545Notes

Reaction equation

HRID 734545 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[N:34]2[CH2:39][CH2:38][N:37](CCC3C=C(C=CC=3)N)[CH2:36][CH2:35]2)[N:25]=1.[N:49]1([C:54]2[CH:55]=[C:56]([CH2:60][C:61]([OH:63])=O)[CH:57]=[CH:58][CH:59]=2)[CH:53]=[CH:52][CH:51]=[N:50]1>CN(C)C=O>[CH3:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[N:34]2[CH2:39][CH2:38][N:37]([C:61](=[O:63])[CH2:60][C:56]3[CH:57]=[CH:58][CH:59]=[C:54]([N:49]4[CH:53]=[CH:52][CH:51]=[N:50]4)[CH:55]=3)[CH2:36][CH2:35]2)[N:25]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21062671[3-(1H-Pyrazol-1-yl)phenyl]acetic acidHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Product 1

HCID 498512602-Methyl-5-(4-{[3-(1H-pyrazol-1-yl)phenyl]acetyl}-1-piperazinyl)quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC.HCl (1.5 eq), HOBt (2 eq) and 2-methyl-5-(1-piperazinyl)quinoline (D3) (1 eq) were added sequentially to a stirred solution of [3-(1H-pyrazol-1-yl)phenyl]acetic acid (D19) (1.1 eq) in dimethylformamide at room temperature under an inert atmosphere.

Sources & evidence

ORD record
ord-f8578f3f6b1d47b88215457bde9fbf4a
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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