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Triethylamine → N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide

HRID 1881804
Notes
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Reaction equation

HRID 1881804 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH2:11][NH2:12].C(N(CC)CC)C.Cl[C:21](=[O:27])[C:22]([O:24]CC)=O.[CH3:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][NH2:37])=[N:33][CH:34]=1>C(#N)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH2:11][NH:12][C:22](=[O:24])[C:21]([NH:37][CH2:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH3:28])=[CH:34][N:33]=1)=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 230682952-(5-Methylpyridin-2-yl)ethan-1-amineHCID 67265413HCID 67265413, compound

Product 1

HCID 11210019N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamideYield 30%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a mixture of 1.8 g of (2-methoxy-4-methylphenyl)methanamine hydrochloride salt and triethylamine (5.1 mL, 3 equiv.) in dry acetonitrile (45 mL) was added ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 equiv.) dropwise at 0° C. under nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 equiv.) was added. The reaction was heated at reflux for 24 hours. After removal of the solvent, the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and evaporated. The residue was washed with methyl t-butyl ether (20 mL) and recrystallized from ethanol to give 1.3 g of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide as a white powder (yield 30%).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 24 hours
  4. customAfter removal of the solvent
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. washThe residue was washed with methyl t-butyl ether (20 mL)
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-84e5853748824ebabc210714a1b5e19d
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318947B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes