Piperazine → HCID 66744426, compound

HRID 1959398Notes

Reaction equation

HRID 1959398 reaction equation
Br[C:2]1[N:3]=[C:4]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CN(C=O)C.CCOC(C)=O.O>[CH3:28][C:26]1[O:25][N:24]=[C:23]([C:4]2[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=[C:2]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:3]=2)[N:27]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 86662081HCID 86662081, compound

Product 1

HCID 66744426HCID 66744426, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl N-[5-bromo-3-(5-methyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (200 mg, 0.4383 mmol) in DMF (1.562 mL) was treated with piperazine (377.5 mg, 4.383 mmol) and the reaction mixture heated at 100° C. for 30 minutes. The reaction was allowed to cool to RT and diluted with EtOAc/Water and the layers separated. The organic layer was washed with water (3×), dried (MgSO4), filtered and concentrated in vacuo. The material was used crude in the next step (150 mg, 67% Yield). 1H NMR (400.0 MHz, CDCl3) d 1.37 (18H, s), 2.73 (3H, s), 3.14 (4H, m) ppm; MS (ES+) 462.14

Workup

  1. temperatureto cool to RT
  2. customthe layers separated
  3. washThe organic layer was washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e4bd46553e44a8fbf64e03c7254e71a
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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