HCID 10074262, compound → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(3-dimethylamino-propyl)-pyrazin-2-yl]-propionamide

HRID 719876Notes

Reaction equation

HRID 719876 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[C:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:28][CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 10074262HCID 10074262, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 100513632(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(3-dimethylamino-propyl)-pyrazin-2-yl]-propionamideYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(3-dimethylamino-prop-1-ynyl)-pyrazin-2-yl]-propionamide (prepared as in Example 11, 190 mg, 0.389 mmol) in methanol (20 ml) was treated with 10% palladium on activated carbon (65 mg). The resulting reaction mixture was stirred under a positive pressure of hydrogen gas (balloon) overnight. At this time, the catalyst was removed by filtration through a pad of celite, and the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/1 methylene chloride/methanol) afforded the 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(3-dimethylamino-propyl)-pyrazin-2-yl]-propionamide (120 mg, 63%) as a solid: (ES)+-HRMS m/e calcd for C24H33ClN4O3S (M+H)+ 493.2035, found 493.2041.

Workup

  1. customThe resulting reaction mixture
  2. customAt this time, the catalyst was removed by filtration through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-56e0538362ed49e8a7cf35cf108cafd7
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

Loading…