4-Quinolinecarboxylic acid → 5-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-[1-(quinolin-4-ylcarbonyl)piperidin-4-yl]-2,4-dihydro-3H-pyrazol-3-one

HRID 524183Notes

Reaction equation

HRID 524183 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([C:36](O)=[O:37])=[CH:28][CH:27]=1>>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:36]([C:29]4[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:26]=[CH:27][CH:28]=4)=[O:37])[CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

3

Reactant 2

HCID 102434-Quinolinecarboxylic acidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462049655-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-[1-(quinolin-4-ylcarbonyl)piperidin-4-yl]-2,4-dihydro-3H-pyrazol-3-one

Procedure

The title compound is prepared analogously as described for GP2-WU2 using 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1) and quinoline-4-carboxylic acid as starting compounds. The crude product is purified by chromatography (silica gel and DCM/diethyl ether/methanol=5:5:1) to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by chromatography (silica gel and DCM/diethyl ether/methanol=5:5:1)

Sources & evidence

ORD record
ord-a49dd1638d2e4862ae15612ecf80286a
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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