Carbon Tetrachloride → (4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone

HRID 551594노트

반응식

HRID 551594 반응식
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([CH:11](Br)Br)=[CH:7][N:6]=1)=[O:4].COC([C:18]1[CH:23]=[N:22][C:21](C)=[CH:20][N:19]=1)=O.Br[N:26]1[C:30](=O)[CH2:29][CH2:28][C:27]1=O.[C:33](OOC(=O)C1C=CC=CC=1)(=O)[C:34]1C=CC=C[CH:35]=1.[C:51](Cl)(Cl)(Cl)Cl>>[CH:34]([N:19]1[CH2:18][CH2:23][N:22]([C:3]([C:5]2[CH:10]=[N:9][C:8]([CH2:11][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:51]3)=[CH:7][N:6]=2)=[O:4])[CH2:21][CH2:20]1)([CH3:35])[CH3:33]

참가 물질

6

반응물 5

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 4650652-Pyrazinecarboxylic acid, 5-methyl-, methyl esterHCID 67188344Methyl 5-(dibromomethyl)pyrazine-2-carboxylate

생성물 1

HCID 11544498(4-Isopropyl-piperazin-1-yl)-(5-piperidin-1-ylmethylpyrazin-2-yl)-methanone수율 31%

실험 절차

5-Dibromomethyl-pyrazine-2-carboxylic acid methyl ester. 5-Methyl-pyrazine-2-carboxylic acid methyl ester (1.60 g, 10.5 mmol; Macdonald, S. J. F. et al. J. Med. Chem. 2002, 45(18):3878-3890.), N-bromosuccinimide (5.62 g, 31.6 mmol), and dibenzoyl peroxide (0.255 g, 1.05 mmol) were dissolved in CCl4 (80 mL). The mixture was heated at reflux for 18 h. The reaction mixture was cooled and washed with 10% aq. Na2SO3 (2×20 mL) and H2O (1×30 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to yield a brown oily crude material (2.41 g). The crude product was purified (SiO2: 0-20% ethyl acetate/hexanes) to give the title compound (1.00 g, 31%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. washwashed with 10% aq. Na2SO3 (2×20 mL) and H2O (1×30 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oily crude material (2.41 g)
  9. customThe crude product was purified (SiO2: 0-20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-1e6cc00fb549435db6fa74da074c38f6
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947718B2

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