1-Methylpiperazine → HCID 86670919, compound

HRID 1186492Notes

Reaction equation

HRID 1186492 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16](Cl)[C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>CC(O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16]([N:22]4[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]4)[C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 86670917HCID 86670917, compound

Product 1

HCID 86670919HCID 86670919, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine (from Example 38 supra) (1.44 g, 4.65 mmol), 1-methylpiperazine (2.1 g, 21 mmol), and diisopropylethylamine (2.7 g, 21 mmol) in 2-propanol (300 mL) was stirred and heated at reflux overnight. The solution was then cooled to room temperature, concentrated under reduced pressure. The resulted solid was washed with water, partitioned between CH2Cl2 and brine. The organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1) to give 3-(6-bromo-pyridin-2-yl)-8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazine. (Yield 1.27 g, 73%).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. washThe resulted solid was washed with water
  5. custompartitioned between CH2Cl2 and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe crude product was purified by chromatography (CH2Cl2:CH3OH, 100:1)

Sources & evidence

ORD record
ord-0ec757afcb0b41faa58b2172679a888b
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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