2-(5-Chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone → 2-(3-Amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

HRID 11674Notes

Reaction equation

HRID 11674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:27]([O-])=O)[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH3:26])=[O:11])=[N:6][CH:7]=1.[H][H]>C(O)C.[Pt](=O)=O>[NH2:27][C:4]1[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH3:26])=[O:11])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 696557252-(5-Chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 696554982-(3-Amino-5-chloro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanoneYield 86.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(5-chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.96 g, 2.3 mmol) in ethanol (25 mL) was added platinum dioxide on carbon (0.90 mg, 5% on carbon). The reaction was subject to 35 psi hydrogen gas for 20 minutes. The reaction was filtered through celite, concentrated in vacuo and chromatographed on silica gel to give the title compound (0.78 g).

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated in vacuo
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-9f991950fe5e4b9e8a888fb8464d34a7
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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