Water → HCID 25186174, compound

HRID 2065765Notes

Reaction equation

HRID 2065765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH:13]([C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl[C:34]1[C:35]([CH3:41])=[N:36][CH:37]=[C:38]([CH3:40])[N:39]=1.C(N(CC)CC)C.O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH:13]([C:25]([N:27]3[CH2:28][CH2:29][N:30]([C:37]4[C:38]([CH3:40])=[N:39][CH:34]=[C:35]([CH3:41])[N:36]=4)[CH2:31][CH2:32]3)=[O:26])[CH2:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 667713-Chloro-2,5-dimethylpyrazineHCID 68729752HCID 68729752, compound

Product 1

HCID 25186174HCID 25186174, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[4-(3-Chloro-benzenesulfonyl)-1-(4-fluoro-2-methyl-phenyl)-piperazin-2-yl]-piperazin-1-yl-methanone (60 mg), 3-chloro-2,5-dimethylpyrazine (18.1 μL) and triethylamine (20.8 μL) in acetonitrile (1 mL) were heated to 170° C. in the microwave. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by chromatography (SiO2, n-heptane/ethyl acetate 1:2) gave [4-(3-chloro-benzenesulfonyl)-1-(4-fluoro-2-methyl-phenyl)-piperazin-2-yl]-(3′,6′-dimethyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-methanone as a yellow oil, MS: 587.3 ([M+H, 1Cl]+).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (SiO2, n-heptane/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-8da40a1548e04c8e8c6c7cbb4f9c71b0
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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