Triethylamine → 6-(3,3-Diethoxyprop-1-ynyl)-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1640689노트

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HRID 1640689 반응식
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[C:5](=[O:13])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:3]=1[CH3:24].[CH2:25]([O:27][CH:28]([O:31][CH2:32][CH3:33])[C:29]#[CH:30])[CH3:26].CCN(CC)CC>C1COCC1.[Cu]I>[CH2:25]([O:27][CH:28]([O:31][CH2:32][CH3:33])[C:29]#[C:30][C:2]1[N:7]=[C:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[C:5](=[O:13])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:3]=1[CH3:24])[CH3:26]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 662853,3-DiethoxypropyneHCID 667390956-Bromo-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

생성물 1

HCID 667387186-(3,3-Diethoxyprop-1-ynyl)-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide수율 25.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

6-Bromo-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (0.10 g, 0.247 mmol), propargylaldehyde diethyl acetal (0.48 mg, 0.370 mmol), copper(I) iodide (0.001 mg, 0.005 mmol) and Et3N (1 ml) in THF (1 ml) were placed in a glass tube for microwave synthesis. The mixture was degassed with argon and Pd(Cl2) (PPh3)2 (0.007 g) was added. The tube was sealed and heated with stirring at 60° C. (150 W) in a microwave heater for 20 minutes. The mixture was diluted with EtOAc (5 ml) and filtered. The solution was concentrated in vacuo and was then purified on silica to give the title compound (28 mg, 25%).

후처리

  1. customThe mixture was degassed with argon and Pd(Cl2) (PPh3)2 (0.007 g)
  2. additionwas added
  3. customThe tube was sealed
  4. temperatureheated
  5. additionThe mixture was diluted with EtOAc (5 ml)
  6. filtrationfiltered
  7. concentrationThe solution was concentrated in vacuo
  8. customwas then purified on silica

출처 및 근거

ORD 기록
ord-067cfa253cff4a4083b4995013c30ace
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114881B2

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