4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide → 4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amide

HRID 492993Notes

Reaction equation

HRID 492993 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]4[CH2:29][CH2:28][CH2:27]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26]4[CH2:29][CH2:28][CH2:27]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 1

HCID 576776864-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide

Product 1

HCID 576775264-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-aminophenoxy)pyridin-2-yl]amideYield 61.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (122 mg) was dissolved in tetrahydrofuran (3 ml) and methanol (3 ml). 10% Palladium carbon (61 mg) was added, followed by stirring under a hydrogen atmosphere for 22 hrs. The reaction mixture was filtered to remove the catalyst, and the catalyst was washed with methanol. The filtrate was concentrated under reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=9:1). Fractions containing the target compound were concentrated to give a crude product of the titled compound (70 mg) as a pale yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. washthe catalyst was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue, which
  6. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:methanol=9:1)
  7. additionFractions containing the target compound
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-9206415103584da38e5e506488c8a256
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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