4-Amino-3-(trifluoromethyl)benzoic acid → 2-(1-{[4-Amino-3-(trifluoromethyl)phenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524206Notes

Reaction equation

HRID 524206 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].[NH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][C:28]=1[C:36]([F:39])([F:38])[F:37]>>[NH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:20]2[CH2:21][CH2:22][CH:17]([N:15]3[C:14](=[O:23])[C:13]([CH3:25])([CH3:24])[C:12]([C:6]4[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=4)=[N:16]3)[CH2:18][CH2:19]2)=[O:32])=[CH:29][C:28]=1[C:36]([F:37])([F:38])[F:39]

Participants

3

Reactant 2

HCID 32542864-Amino-3-(trifluoromethyl)benzoic acidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462066262-(1-{[4-Amino-3-(trifluoromethyl)phenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Procedure

The title compound is prepared analogously as described for GP3 using 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1) and 4-amino-3-(trifluoromethyl)benzoic acid as starting compounds. The crude product is purified by column chromatography (silica gel and DCM/methanol=4:1) and crystallization from methanol to yield the title compound.

Workup

  1. customThe title compound is prepared analogously
  2. customThe crude product is purified by column chromatography (silica gel and DCM/methanol=4:1) and crystallization from methanol

Sources & evidence

ORD record
ord-05370ba69d794b66adadc2a9a43d9cb2
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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