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

HRID 493353

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-8357bf44236049ea948923a54d39262c
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534794B2

Linked notes

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