Quinoline-7-carboxylic acid → 5-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-[1-(quinolin-7-ylcarbonyl)piperidin-4-yl]-2,4-dihydro-3H-pyrazol-3-one

HRID 524187

Reaction equation

HRID 524187 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]=[C:33]([C:36](O)=[O:37])[CH:34]=2)[CH:29]=[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:33]4[CH:34]=[C:35]5[C:30]([CH:29]=[CH:28][CH:27]=[N:26]5)=[CH:31][CH:32]=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 599475Quinoline-7-carboxylic acidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462052965-(3,4-Dimethoxyphenyl)-4,4-dimethyl-2-[1-(quinolin-7-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-7-carboxylic acid as starting compounds. The crude product is purified by chromatography (amino phase silica gel and DCM) and by crystallization from DCM and diethyl ether to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by chromatography (amino phase silica gel and DCM) and by crystallization from DCM and diethyl ether

Sources & evidence

ORD record
ord-94ba7250da1b4dc1b313718722120abd
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Linked notes

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