3-[2-(4-{5-[1,1,1,3,3,3-Hexafluoro-2-(4-methoxybenzyloxy)propan-2-yl]-4-propylpyridin-2-yl}piperazin-1-yl)ethyl]-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione → 3-(2-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl)-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione

HRID 1038518Notes

Reaction equation

HRID 1038518 reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]([C:18]1[C:19]([CH2:50][CH2:51][CH3:52])=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][N:32]3[C:36](=[O:37])[C:35]([C:39]4[CH:44]=[CH:43][C:42]([O:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=4)([CH3:38])[NH:34][C:33]3=[O:49])[CH2:26][CH2:25]2)=[N:22][CH:23]=1)([O:8]CC1C=CC(OC)=CC=1)[C:4]([F:7])([F:6])[F:5]>C(OCC)(=O)C.[C].[Pd]>[F:7][C:4]([F:5])([F:6])[C:3]([C:18]1[C:19]([CH2:50][CH2:51][CH3:52])=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][N:32]3[C:36](=[O:37])[C:35]([C:39]4[CH:40]=[CH:41][C:42]([O:45][CH:46]([CH3:47])[CH3:48])=[CH:43][CH:44]=4)([CH3:38])[NH:34][C:33]3=[O:49])[CH2:26][CH2:25]2)=[N:22][CH:23]=1)([OH:8])[C:2]([F:53])([F:1])[F:54]

Participants

4

Reactant 1

HCID 866471813-[2-(4-{5-[1,1,1,3,3,3-Hexafluoro-2-(4-methoxybenzyloxy)propan-2-yl]-4-propylpyridin-2-yl}piperazin-1-yl)ethyl]-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione

Product 1

HCID 595639123-(2-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl)-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dioneYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-[2-(4-{5-[1,1,1,3,3,3-Hexafluoro-2-(4-methoxybenzyloxy)propan-2-yl]-4-propylpyridin-2-yl}piperazin-1-yl)ethyl]-5-[4-(1-methylethoxy)phenyl]-5-methylimidazolidine-2,4-dione (10 mg, 0.0131 mmol) was dissolved in ethyl acetate (2 mL), added palladium carbon (1.0 mg), and the mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere. The reaction solution was filtered through a pad of celite, and concentrated in vacuo. The title compound (7.3 mg (yield 86%)) was obtained as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-717a7faf55514353b74499b0e07c2a9b
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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