4-Methylpiperazine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide → 4-Methylpiperazine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amide

HRID 492678Notes

Reaction equation

HRID 492678 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>CO.[C].[Pd]>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:24]=1

Participants

4

Reactant 1

HCID 576774434-Methylpiperazine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide

Product 1

HCID 576775974-Methylpiperazine-1-carboxylic acid [4-(4-amino-2-fluorophenoxy)pyridin-2-yl]amideYield 62.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-methylpiperazine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (339 mg, 0.903 mmol) in methanol (30 ml) was added 10% palladium carbon (100 mg), followed by stirring under a hydrogen atmosphere at room temperature for 2 hrs. The catalyst was filtered. The filtrate was concentrated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, hexane:ethyl acetate=1:1, then ethyl acetate) to provide the titled compound (196 mg, 62.8%) as a yellow oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationThe filtrate was concentrated under a reduced pressure
  3. customto give a residue, which
  4. customwas then purified by silica gel column chromatography (Fuji Silysia NH, hexane

Sources & evidence

ORD record
ord-19664bfffe6a44fa82cc543534b20f1e
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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