Triethylamine → HCID 67265766, compound

HRID 1686130Notes

Reaction equation

HRID 1686130 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:15](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]N)=[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][N:12]([CH2:36][CH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH3:28])=[CH:34][N:33]=1)[C:22](=[O:24])[C:21]([NH2:15])=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 23068295830348-34-0HCID 67265413HCID 67265413, compound

Product 1

HCID 67265766HCID 67265766, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 N′-(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-4fca418732464d858780166cb78e8d94
Source dataset
uspto-grants-2012_04
Patent number
US08148536B2

Reaction notes

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