Potassium Carbonate → Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate

HRID 1789764Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[C:25](Cl)=[N:24][S:23][N:22]=1>CC#N.CCOC(C)=O.O>[Cl:20][C:21]1[C:25]([N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)=[N:24][S:23][N:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-Boc-piperazine (2.97 g, 15.9 mmol), K2CO3 (2.20 g, 15.9 mmol) and 3,4-dichloro-1,2,5-thiadiazole (1.5 mL, 15.9 mmol) in CH3CN (30 mL) was stirred at 100° C. for 19 h and at room temperature for 4 days. The reaction mixture was then diluted with EtOAc and water. The organic phase was dried (K2CO3) and the solvent was removed under reduced pressure. The residue was purified by chromatography on two successive silica gel columns eluting with hexane/EtOAc (1:1) and (7:3), respectively. This gave 1.54 g (31%) of the title product as a yellow solid.

Workup

dry with materialThe organic phase was dried (K2CO3)
customthe solvent was removed under reduced pressure
customThe residue was purified by chromatography on two successive silica gel columns
washeluting with hexane/EtOAc (1:1) and (7:3)

Sources & evidence

ORD record: ord-51b277b3a8fa4880acb62b1176d21922
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071180B2

Reaction notes

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