1-(5-Methyl-4-trifluoromethyl-thiazol-2-yl)-piperazine → [5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(5-methyl-4-trifluoromethyl-thiazol-2-yl)-piperazin-1-yl]-methanone

HRID 1352349Notes

Reaction equation

HRID 1352349 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].[CH3:21][C:22]1[S:26][C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:24][C:23]=1[C:33]([F:36])([F:35])[F:34]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([C:10]([N:30]2[CH2:31][CH2:32][N:27]([C:25]3[S:26][C:22]([CH3:21])=[C:23]([C:33]([F:36])([F:34])[F:35])[N:24]=3)[CH2:28][CH2:29]2)=[O:12])[CH:13]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211001891-(5-Methyl-4-trifluoromethyl-thiazol-2-yl)-piperazineHCID 211003065-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid

Product 1

HCID 11541197[5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(5-methyl-4-trifluoromethyl-thiazol-2-yl)-piperazin-1-yl]-methanoneYield 61%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example A2) and 1-(5-methyl-4-trifluoromethyl-thiazol-2-yl)-piperazine (Example 54(a)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) followed by trituration in pentane to yield the title compound as a white crystalline solid (yield 61%). MS (m/e): 546.3 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-5f20ee6dd5d34403836166746fb7e4d3
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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