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

HRID 1518597노트

반응식

HRID 1518597 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c9448ebf06ef4e66836935ed6c69b678
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09072313B2

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