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

HRID 492990Notes

Reaction equation

HRID 492990 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][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]([CH2:20][CH2:21][N:22]3[CH2:25][CH2:24][CH2:23]3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1>O1CCCC1.CO.[C].[Pd]>[NH2:30][C:28]1[CH:27]=[CH:26][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[CH2:25][CH2:24][CH2:23]4)[CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:29]=1

Participants

5

Reactant 1

HCID 576773874-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide

Product 1

HCID 576777584-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(4-amino-2fluorophenoxy)pyridin-2-yl]amideYield 66.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(Azetidin-1-yl)ethyl]piperazine-1-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (114 mg) was dissolved in tetrahydrofuran (3 ml) and methanol (3 ml). 10% Palladium carbon (55 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 (71 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-afb4708aac7945e5bc68eee78f85a792
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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