Sodium Hydroxide → 2-(1-{[5-(Cyclopropylmethoxy)-2-methylphenyl]carbonyl}piperidin-4-yl)-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 524247Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]([CH3:34])([CH3:33])[C:13](=[O:32])[N:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([C:24]4[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][C:25]=4[CH3:31])=[O:23])[CH2:18][CH2:17]3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:36][CH:37]1[CH2:39][CH2:38]1.[OH-].[Na+]>C(O)C>[CH:37]1([CH2:36][O:30][C:28]2[CH:27]=[CH:26][C:25]([CH3:31])=[C:24]([C:22]([N:19]3[CH2:20][CH2:21][CH:16]([N:14]4[C:13](=[O:32])[C:12]([CH3:34])([CH3:33])[C:11]([C:5]5[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)=[N:15]4)[CH2:17][CH2:18]3)=[O:23])[CH:29]=2)[CH2:39][CH2:38]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 0.35 g of 5-(3,4-dimethoxyphenyl)-2-{1-[(5-hydroxy-2-methylphenyl)carbonyl]piperidin-4-yl}-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 85) and 0.11 ml (bromomethyl)cyclopropane in 8 ml ethanol is treated with 0.11 ml 10n aqueous sodium hydroxide solution and stirred under a blanket of nitrogen for about 16 h at 80° C. until the reaction is completed largely according to TLC analysis. The solvent is evaporated under reduced pressure, and the resulting crude product is purified by chromatography (amino phase silica gel and DCM) to yield the title compound.

Workup

customThe solvent is evaporated under reduced pressure
customthe resulting crude product is purified by chromatography (amino phase silica gel and DCM)

Sources & evidence

ORD record: ord-7136dc10c7014bdbb8c6f633757af298
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340522B2

Reaction notes

Loading…