Trifluoroacetic acid → 2-((3-Cyano-4-(5-nitropyridin-2-yloxy)phenyl)(methyl)amino)acetic acid

HRID 884137Notes

Reaction equation

HRID 884137 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:19]([CH3:28])[CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([N:19]([CH3:28])[CH2:20][C:21]([OH:23])=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68527093t-Butyl 2-((3-cyano-4-(5-nitropyridin-2-yloxy)phenyl)(methyl)amino)acetate

Product 1

HCID 685237202-((3-Cyano-4-(5-nitropyridin-2-yloxy)phenyl)(methyl)amino)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 2-((3-cyano-4-(5-nitropyridin-2-yloxy)phenyl)(methyl)amino)acetate (1.2 g, 3.1 mmol) in dichloromethane (12 mL) was added trifluoroacetic acid (12 mL), and the resulting reaction solution was stirred at room temperature for 5 hours. The solvent was evaporated, and water was added to the residue, and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated, to thereby yield crude 2-((3-cyano-4-(5-nitropyridin-2-yloxy)phenyl)(methyl)amino)-acetic acid. To a solution of this compound in DMF (24 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (659 mg, 3.4 mmol), 1-hydroxybenzotriazole monohydrate (526 mg, 3.4 mmol) and 1-piperonylpiperazine (757 mg, 3.4 mmol), and the resulting reaction solution was stirred for 8 hours at room temperature. Water was added to the reaction solution and extracted with ethyl acetate. The ethyl acetate layer was then washed with, in order, saturated aqueous sodium bicarbonate solution, water and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography (ethyl acetate), to thereby yield 412 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. customThe solvent was evaporated
  3. additionwater was added to the residue
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4b972750cdcb4138ae93d3ceb97c7f3c
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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