HCID 90224890, compound → HCID 74766529, compound

HRID 1487097Notes

Reaction equation

HRID 1487097 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:35]2[C:39]([CH3:41])([CH3:40])[C:38](=[O:42])[NH:37][C:36]2=[O:43])[CH:5]=[C:6]([CH3:34])[C:7]=1/[CH:8]=[CH:9]/[S:10]([N:13]1[CH2:33][CH2:32][C:16]2([N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[NH:18][C:17]2=[O:31])[CH2:15][CH2:14]1)(=[O:12])=[O:11]>FC(F)(F)CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[CH:3]=[C:4]([N:35]2[C:39]([CH3:40])([CH3:41])[C:38](=[O:42])[NH:37][C:36]2=[O:43])[CH:5]=[C:6]([CH3:34])[C:7]=1[CH2:8][CH2:9][S:10]([N:13]1[CH2:33][CH2:32][C:16]2([N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=3)[NH:18][C:17]2=[O:31])[CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

4

Reactant 1

HCID 90224890HCID 90224890, compound

Product 1

HCID 74766529HCID 74766529, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A mixture of (E)-1-(3,5-dimethyl-4-(2-((4-oxo-2-(3-(trifluoromethyl)phenyl)-1,3,8-triazaspiro[4.5]deca-1-en-8-yl)sulfonyl)vinyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (195 mg, 0.316 mmol) and palladium hydroxide/carbon (20% Pd) (wetted with approximately 50% water) (195 mg, 0.139 mmol) in 2,2,2-trifluoroethanol (6 mL) was stirred at room temperature for 14 hours under hydrogen atmosphere. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane) to afford 1-(3,5-dimethyl-4-(2-((4-oxo-2-(3-(trifluoromethyl)phenyl)-1,3,8-triazaspiro[4.5]deca-1-en-8-yl) sulfonyl)ethyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (121 mg, 62%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d9c47d76de8c4354b3c07b878576e605
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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