1-[4-(2,2,2-Trifluoro-ethyl)-thiazol-2-yl]-piperazine → [5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-{4-[4-(2,2,2-trifluoro-ethyl)-thiazol-2-yl]-piperazin-1-yl}-methanone

HRID 1352352Notes

Reaction equation

HRID 1352352 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].[F:21][C:22]([F:36])([F:35])[CH2:23][C:24]1[N:25]=[C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[S:27][CH:28]=1>>[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:32]2[CH2:33][CH2:34][N:29]([C:26]3[S:27][CH:28]=[C:24]([CH2:23][C:22]([F:36])([F:21])[F:35])[N:25]=3)[CH2:30][CH2:31]2)=[O:12])[CH:13]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211001721-[4-(2,2,2-Trifluoro-ethyl)-thiazol-2-yl]-piperazineHCID 211003065-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid

Product 1

HCID 21100307[5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-{4-[4-(2,2,2-trifluoro-ethyl)-thiazol-2-yl]-piperazin-1-yl}-methanoneYield 29%

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-[4-(2,2,2-trifluoro-ethyl)-thiazol-2-yl]-piperazine (Example 56(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 29%). 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-4c42e2ae7a904aaba3b273d87dc31177
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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