2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide

HRID 719951Notes

Reaction equation

HRID 719951 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[C:23][C:24]3([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:31][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH2:23][C:24]3([OH:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

4

Reactant 1

HCID 100072342(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide

Product 1

HCID 104822862(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamideYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethynyl)-pyrazin-2-yl]-propionamide (prepared as in Example 50, 200 mg, 0.376 mmol) in methanol (30 mL) was treated with 10% palladium on activated carbon (39 mg). The reaction mixture was then placed on a Parr shaker under a hydrogen atomsphere of 50 psi for 4 h. The mixture was filtered, and solvents were concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide (169 mg, 84%) as a fluffy solid: (ES)+-HRMS m/e calcd for C26H34ClN3O5S (M+H)+ 536.1981, found 536.1988.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationsolvents were concentrated in vacuo

Sources & evidence

ORD record
ord-a63ec33513b24e0ab5adff489d3c0e03
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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