Piperazine → Tert-butyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-ylcarbamate

HRID 1959363Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Tert-butyl 5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-ylcarbamate (2.56 g, 6.121 mmol) was dissolved in DMF (20 mL) and piperazine (5.272 g, 61.21 mmol) was added. The mixture was heated to 100° C. for 30 minutes, allowed to cool to ambient temperature and the solvent removed in vacuo. The mixture was partitioned between DCM/Water and the organic layer washed with brine, dried over MgSO4, filtered and concentrated to give a yellow oil. The resultant residue was purified on silica gel by flash column chromatography (0-10% MeOH/DCM) to afford the title compound (2.29 g, 89% Yield).

Workup

temperatureto cool to ambient temperature
customthe solvent removed in vacuo
customThe mixture was partitioned between DCM/Water
washthe organic layer washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give a yellow oil
customThe resultant residue was purified on silica gel by flash column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-ab0918862cf54d698b1a9b5e564ab28b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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