1-(2-(Methylsulfonyl)ethyl)piperazine → tert-butyl N-tert-butoxylcarbonyl-5-(4-(2-(methylsulfonyl)ethyl)piperazin-1-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-ylcarbamate

HRID 1959414Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19](Br)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][S:35]([CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)(=[O:37])=[O:36]>CN(C=O)C>[O:5]([C:6]([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19]([N:43]2[CH2:42][CH2:41][N:40]([CH2:39][CH2:38][S:35]([CH3:34])(=[O:36])=[O:37])[CH2:45][CH2:44]2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

tert-butyl N-tert butoxycarbonyl-5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-ylcarbamate (75 mg, 0.13 mmol) was dissolved in DMF (1 mL) and 1-(2-(methylsulfonyl)ethyl)piperazine (77 mg, 0.40 mmol) was added. The reaction mixture was heated at 100° C. in a sealed tube overnight. The reaction mixture was cooled to room temperature and partitioned between CH2Cl2 and water and the layers separated using a phase separation cartridge. The organic layer was concentrated in vacuo to give the product (84.01 mg, 0.13 mmol)

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between CH2Cl2 and water
customthe layers separated
customa phase separation cartridge
concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record: ord-3fd441451b424e0bb940a70424ffa81d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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