3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl Ester → HCID 69655855, compound

HRID 11683Notes

Reaction equation

HRID 11683 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH:5]=[CH:6][C:7]1[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)[CH3:2].[H][H]>C(O)C.[Pt]=O>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 696553743-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 69655855HCID 69655855, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic acid ethyl ester (0.102 g, 0.21 mmol) in ethanol (20 mL) was added platinum oxide (0.010 g). The reaction mixture was shaken under positive pressure of hydrogen gas (20 psi) for 20 minutes. The resulting mixture was filtered through a pad of celite, the filter cake was washed with ethanol, and the combined filtrate was concentrated in vacuo to give the title compound (0.081 g).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of celite
  2. washthe filter cake was washed with ethanol
  3. concentrationthe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-369032f037b84c4e9ebb3e763ca261b0
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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