HCID 67431241, compound → (4R)-1-(5-chloro-3-[5-(5-hydroxypentyl)-2-methoxyphenyl]-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolinamide

HRID 1662794Notes

Reaction equation

HRID 1662794 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:26])([F:25])[F:24])(=[O:13])=[O:12])[C:6](=[O:27])[C:5]2([N:42]1[CH2:51][C@H:50]([OH:52])[CH2:49][C@H:43]1[C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[C:28]1[CH:33]=[C:32]([CH2:34][CH:35]=[CH:36][CH2:37][CH2:38][OH:39])[CH:31]=[CH:30][C:29]=1[O:40][CH3:41]>CO.[C].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][C:23]([F:24])([F:26])[F:25])(=[O:12])=[O:13])[C:6](=[O:27])[C:5]2([N:42]1[CH2:51][C@H:50]([OH:52])[CH2:49][C@H:43]1[C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[C:28]1[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH:31]=[CH:30][C:29]=1[O:40][CH3:41]

Participants

4

Reactant 1

HCID 67431241HCID 67431241, compound

Product 1

HCID 59867860(4R)-1-(5-chloro-3-[5-(5-hydroxypentyl)-2-methoxyphenyl]-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolinamideYield 42.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Under hydrogen atmosphere, suspension of 200 mg of the compound obtained in Example 262 and 20 mg of 5% palladium-carbon in MeOH (2 ml) was stirred at room temperature for one hour. The insoluble matter was separated by filtration with celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=30/1 to 15/1; v/v) to obtain 86 mg of the title compound (amorphous).

Workup

  1. customThe insoluble matter was separated by filtration with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silicagel 60N; mobile phase: CHCl3/MeOH=30/1 to 15/1; v/v)

Sources & evidence

ORD record
ord-08d463de8b7147c2b5f454d4b87e801d
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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