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

HRID 551594Notes

Reaction equation

HRID 551594 reaction equation
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]

Participants

6

Reactant 5

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

Product 1

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

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-1e6cc00fb549435db6fa74da074c38f6
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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