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

HRID 1881801노트

반응식

HRID 1881801 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH2:10][NH2:11].CCN(CC)CC.Cl[C:20](=[O:26])[C:21]([O:23]CC)=O.[CH3:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][NH2:36])=[N:32][CH:33]=1>CC#N>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH2:10][NH:11][C:21](=[O:23])[C:20]([NH:36][CH2:35][CH2:34][C:31]1[CH:30]=[CH:29][C:28]([CH3:27])=[CH:33][N:32]=1)=[O:26]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 230682952-(5-Methylpyridin-2-yl)ethan-1-amineHCID 586074662-Methoxy-4-methylbenzenemethanamine

생성물 1

HCID 11210019N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide수율 15%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

A mixture of 2 g of (2-methoxy-4-methylphenyl)methanamine (from step 3) and Et3N (3.7 mL, 2 eq) in dry CH3CN (45 mL) was cooled to 0° C. under N2 atmosphere and ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 eq) was added dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 eq, from step 5) was added. The reaction was heated at reflux for 24 hours. After cooling the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane) and recrystallized from ethyl acetate/hexane and ethanol/water to give 650 mg of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide (15%).

후처리

  1. additionAfter the addition
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 24 hours
  4. temperatureAfter cooling the solvent
  5. customwas removed under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed successively with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was chromatographed on silica gel (eluent: 25-35% acetone in hexane)
  12. customrecrystallized from ethyl acetate/hexane and ethanol/water

출처 및 근거

ORD 기록
ord-7bb5f489c56541d4bebb18619327f63e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318947B2

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