Hydrochloric Acid → 2-[1-(2-Hydroxybenzoyl)piperidin-4-yl]-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 1914139Notes

Reaction equation

HRID 1914139 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[C:21]([C:27]3[C:32]4[CH2:33][C:34]([CH3:37])([CH3:36])[O:35][C:31]=4[C:30]([O:38][CH3:39])=[CH:29][CH:28]=3)=[N:20]2)[CH2:15][CH2:14]1)=[O:12])(=O)C.[OH-].[K+].Cl>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([N:13]1[CH2:14][CH2:15][CH:16]([N:19]2[C:23](=[O:24])[C:22]([CH3:25])([CH3:26])[C:21]([C:27]3[C:32]4[CH2:33][C:34]([CH3:36])([CH3:37])[O:35][C:31]=4[C:30]([O:38][CH3:39])=[CH:29][CH:28]=3)=[N:20]2)[CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 462069562-({4-[3-(7-Methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate

Product 1

HCID 462069572-[1-(2-Hydroxybenzoyl)piperidin-4-yl]-5-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.15 g 2-({4-[3-(7-methoxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate (compound described in example 77) are dissolved in 20 ml of methanol, 0.32 ml 1 M methanolic potassium hydroxide solution are added, and the reaction mixture is stirred at RT for 15 min until the reaction is completed according to TLC analysis. The pH is adjusted to 5.5 with 1 M aqueous hydrochloric acid, the solvents are removed under reduced pressure, and the resulting crude product is purified by column chromatography (silica and DCM/methanol=95:5) to yield the title compound.

Workup

  1. customthe solvents are removed under reduced pressure
  2. customthe resulting crude product is purified by column chromatography (silica and DCM/methanol=95:5)

Sources & evidence

ORD record
ord-842a06a332f04b3ca7675750d15fb6d0
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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