N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide → N-(4-(3-amino-4-(methylamino)phenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide

HRID 1963716Notes

Reaction equation

HRID 1963716 reaction equation
[CH3:1][NH:2][C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:25])[CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[CH2:19][CH2:18]3)[CH:9]=2)=[CH:5][C:4]=1[N+:28]([O-])=O>CO.[Pd]>[NH2:28][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:3]=1[NH:2][CH3:1])[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:25])[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[CH2:19][CH2:18]2)[CH:9]=1

Participants

4

Reactant 1

HCID 69005645N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide

Product 1

HCID 69007913N-(4-(3-amino-4-(methylamino)phenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture containing N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide in methanol with a catalytic amount of 10% Pd/C poisoned with lead was hydrogenated until the disappearance of the yellow color. The reaction was then filtered to remove the catalyst and concentrated to yield N-(4-(3-amino-4-(methylamino)phenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide as a brown oil. HPLC=2.00 min; MS: MH+=385.

Workup

  1. filtrationThe reaction was then filtered
  2. customto remove the catalyst
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1302632b5b9f4f1ab9558e0a53ca1b40
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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