Triethylamine → 4-(5-Propionyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1352394Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[S:20])[N:15]=[CH:16]N(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:29][C:30](=[O:33])[CH2:31][CH3:32]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[S:20][C:29]([C:30](=[O:33])[CH2:31][CH3:32])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 0.83 mmol 4-(dimethylaminomethylene-thiocarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester in 6 ml ethanol were added 2.50 mmol triethylamine and 1.00 mmol 1-bromo-2-butanone. The mixture was heated at 90° C. for 16 h. The reaction mixture was then concentrated in vacuo and the residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a white crystalline solid (yield 72%). MS (m/e): 326.1 (M+H+, 100%).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customthe residue was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-9e12891934734da1ac96e4896b1d3642
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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