3-[2-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-oxoethyl]-5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione → 5-(2,3-Dihydrobenzofuran-5-yl)-3-(2-{4-[6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-3-yl]piperazin-1-yl}-2-oxoethyl)-5-methylimidazolidine-2,4-dione

HRID 1038555Notes

Reaction equation

HRID 1038555 reaction equation
C([O:8][C:9]([C:18]1[N:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30](=[O:49])[CH2:31][N:32]3[C:36](=[O:37])[C:35]([C:39]4[CH:40]=[CH:41][C:42]5[O:46][CH2:45][CH2:44][C:43]=5[CH:47]=4)([CH3:38])[NH:34][C:33]3=[O:48])[CH2:26][CH2:25]2)=[C:20]([CH2:50][CH2:51][CH3:52])[CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])C1C=CC=CC=1>CO.[C].[Pd]>[O:46]1[C:42]2[CH:41]=[CH:40][C:39]([C:35]3([CH3:38])[NH:34][C:33](=[O:48])[N:32]([CH2:31][C:30]([N:27]4[CH2:26][CH2:25][N:24]([C:21]5[CH:22]=[N:23][C:18]([C:9]([OH:8])([C:14]([F:15])([F:16])[F:17])[C:10]([F:11])([F:12])[F:13])=[CH:19][C:20]=5[CH2:50][CH2:51][CH3:52])[CH2:29][CH2:28]4)=[O:49])[C:36]3=[O:37])=[CH:47][C:43]=2[CH2:44][CH2:45]1

Participants

4

Reactant 1

HCID 866472003-[2-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-oxoethyl]-5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione

Product 1

HCID 595639295-(2,3-Dihydrobenzofuran-5-yl)-3-(2-{4-[6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-3-yl]piperazin-1-yl}-2-oxoethyl)-5-methylimidazolidine-2,4-dioneYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-[2-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-oxoethyl]-5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione (13 mg, 0.0170 mmol) was dissolved in methanol (1.5 mL), added palladium carbon (2.0 mg), and the mixture was stirred at room temperature for 2 hours under a hydrogen atomosphere. The reaction solution was filtered through a pad of celite, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone), and the title compound (7.3 mg (yield 80%)) was obtained as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-8ea0f36999d345cc8d3f024c4c42563b
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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