Bromopinacolone → 4-[5-(2,2-Dimethyl-propionyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1352397Notes

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].Br[CH2:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[S:20][C:22]([C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 21642Bromopinacolone

HCID 86606774HCID 86606774, compound

Product 1

HCID 684067804-[5-(2,2-Dimethyl-propionyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl esterYield 87%

Procedure

Prepared in analogy to example 82 (b) from 4-(dimethylaminomethylene-thiocarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester (Example 82(a)) and 1-bromo-pinacolone. The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a white crystalline solid (yield 87%). MS (m/e): 354.3 (M+H+, 100%).

Workup

customThe crude material was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-1856b7618823424ba2f47d02fc32d556
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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