HCID 19024706, compound → HCID 19024777, compound

HRID 249181Notes

Reaction equation

HRID 249181 reaction equation
[CH2:1]([N:8]([C:30]1[CH:31]=[C:32]([CH:57]=[CH:58][CH:59]=1)[C:33]([C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]([CH2:44][CH2:45][CH2:46][C:47]([O:49]CC2C=CC=CC=2)=[O:48])[CH:36]=1)=[O:34])[CH:9]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=1)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCOCC1.[Pd]>[CH2:1]([N:8]([C:30]1[CH:31]=[C:32]([CH:57]=[CH:58][CH:59]=1)[C:33]([C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]([CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[CH:36]=1)=[O:34])[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:12][CH:11]=1)[C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 19024706HCID 19024706, compound

Product 1

HCID 19024777HCID 19024777, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyl 4-[3-[3-[N-benzyl-N-[bis(4-isobutylphenyl)methyl]amino]benzoyl]indol-1-yl]butyrate (24 mg) was dissolved in a mixture of methanol 93 ml) and 1,4-dioxane (3 ml), and 10% palladium on carbon (12 mg) was added. The mixture was stirred under hydrogen atmosphere at room temperature for 5 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was chromatographed on silica gel (2 g) eluting with a mixture of chloroform and methanol (50:1) to give 4-[3-[3-[N-benzyl-N-[bis(4-isobutylphenyl)methyl]amino]benzoyl]indol-1-yl]butyric acid as (14 mg) powder.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated
  4. customThe residue was chromatographed on silica gel (2 g)
  5. washeluting with a mixture of chloroform and methanol (50:1)

Sources & evidence

ORD record
ord-467be03bf1964521b4e06956348231f7
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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