5-(Benzyloxy)-2-methylbenzoic acid → 2-(1-{[5-(Benzyloxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-diethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one
Reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([C:14]2[C:15]([CH3:27])([CH3:26])[C:16](=[O:25])[N:17]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:18]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH3:13])[CH3:3].[CH2:28]([O:35][C:36]1[CH:37]=[CH:38][C:39]([CH3:45])=[C:40]([CH:44]=1)[C:41](O)=[O:42])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36]1[CH:37]=[CH:38][C:39]([CH3:45])=[C:40]([C:41]([N:22]2[CH2:23][CH2:24][CH:19]([N:17]3[C:16](=[O:25])[C:15]([CH3:27])([CH3:26])[C:14]([C:7]4[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH3:13])=[C:5]([O:4][CH2:2][CH3:3])[CH:6]=4)=[N:18]3)[CH2:20][CH2:21]2)=[O:42])[CH:44]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared analogously as described for GP2-WU2 using 5-(3,4-diethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one (compound B2) and 5-(benzyloxy)-2-methylbenzoic acid (compound F1) as starting compounds. The crude product is purified by chromatography (amino phase silica gel and DCM) and by a second chromatography (silica gel and cyclohexane/EA=6:4) to yield the title compound.
Workup
- customThe title compound is prepared analogously
- customThe crude product is purified by chromatography (amino phase silica gel and DCM) and by a second chromatography (silica gel and cyclohexane/EA=6:4)
Sources & evidence
- ORD record
- ord-46c023fe889345e99683d2dc577f0af2
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340522B2
Reaction notes
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