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

HRID 1352392Notes

Reaction equation

HRID 1352392 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C@H: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].Cl.[CH3:22][C:23]1[N:24]=[C:25]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[S:26][C:27]=1[C:28]([F:31])([F:30])[F:29]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([C:10]([N:35]2[CH2:36][CH2:37][N:32]([C:25]3[S:26][C:27]([C:28]([F:31])([F:29])[F:30])=[C:23]([CH3:22])[N:24]=3)[CH2:33][CH2:34]2)=[O:12])[CH:13]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211001771-(4-Methyl-5-trifluoromethyl-thiazol-2-yl)-piperazine hydrochlorideHCID 588633545-Methylsulfonyl-2-[((R)-2,2,2-trifluoro-1-methylethyl)oxy]benzoic acid

Product 1

HCID 58677828[5-Methanesulfonyl-2-((R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(4-methyl-5-trifluoromethyl-thiazol-2-yl)-piperazin-1-yl]-methanoneYield 57%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-((R)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example A16) and 1-(4-methyl-5-trifluoromethyl-thiazol-2-yl)-piperazine hydrochloride (Example 79(g)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) to yield the title compound as a white crystalline solid (yield 57%). MS (m/e): 546.0 (M+H+, 100%).

Workup

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

Sources & evidence

ORD record
ord-249f9ebbe9d24deab22d986a756bc373
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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