Piperazine → HCID 57832796, compound

HRID 729501Notes

Reaction equation

HRID 729501 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CS(C)=O.C(OCC)(=O)C.O>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[N:7]3[N:8]=2)=[CH:12][CH:13]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 4837PiperazineHCID 57832794HCID 57832794, compound

Product 1

HCID 57832796HCID 57832796, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-(4-tert-butyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (20 mg, 60 μM) and piperazine (21 mg, 244 μM) in DMSO was heated at 80° C. for 8 h. The reaction was cooled and diluted with ethyl acetate (25 mL) and water (25 mL). After partitioning the ethyl acetate layer was washed with water (3×) and dried over magnesium sulfate. After filtering and concentration the title compound was obtained in 80% yield. LC/MS (Method A): r.t.=1.26 min. calculated mass=335 [M+H]+=336.

Workup

  1. temperatureThe reaction was cooled
  2. customAfter partitioning the ethyl acetate layer
  3. washwas washed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering
  6. concentrationconcentration the title compound
  7. customwas obtained in 80% yield
  8. customr.t.=1.26 min.

Sources & evidence

ORD record
ord-1f69b957ff284b47b41f1eeddb9b4b25
Source dataset
uspto-grants-2009_09
Patent number
US07582636B2

Reaction notes

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