Potassium Carbonate → N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide

HRID 1963715

Reaction equation

HRID 1963715 reaction equation
[CH3:1][NH:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:18])[CH2:16]Cl)[CH:9]=2)=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].[CH2:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][NH:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:18])[CH2:16][N:29]3[CH2:30][CH2:31][N:26]([CH2:24][CH3:25])[CH2:27][CH2:28]3)[CH:9]=2)=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 59790002N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-chloroacetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-chloroacetamide (1 eq), 1-ethylpiperazine (3 eq), and potassium carbonate (4 eq) was stirred in dimethylformamide at 60° C. for 1 hour. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with water then brine, dried over sodium sulfate and concentrated to give orange solid. Purification on silica gel with 20% methanol in methylene chloride gave N-(4-(4-(methylamino)-3-nitrophenoxy)pyridin-2-yl)-2-(4-ethylpiperazin-1-yl)acetamide as a red solid. HPLC=3.26 min; MS: MH+=415.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give orange solid
  8. customPurification on silica gel with 20% methanol in methylene chloride

Sources & evidence

ORD record
ord-8661fa0d9521497eafd7dae253e1237e
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Linked notes

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