1-(5-Ethanesulfonyl-thiazol-2-yl)-piperazine hydrochloride → [4-(5-Ethanesulfonyl-thiazol-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-methanone

HRID 1352323Notes

Reaction equation

HRID 1352323 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].Cl.[CH2:21]([S:23]([C:26]1[S:30][C:29]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[N:28][CH:27]=1)(=[O:25])=[O:24])[CH3:22]>>[CH2:21]([S:23]([C:26]1[S:30][C:29]([N:31]2[CH2:32][CH2:33][N:34]([C:10]([C:9]3[CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[O:12])[CH2:35][CH2:36]2)=[N:28][CH:27]=1)(=[O:25])=[O:24])[CH3:22]

Participants

3

Reactant 2

HCID 211001851-(5-Ethanesulfonyl-thiazol-2-yl)-piperazine hydrochlorideHCID 211003125-Methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid

Product 1

HCID 21100275[4-(5-Ethanesulfonyl-thiazol-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-methanoneYield 72%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid (Example A3) and 1-(5-ethanesulfonyl-thiazol-2-yl)-piperazine hydrochloride (Example 32(c)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) followed by trituration in ether to yield the title compound as a white crystalline solid (yield 72%). MS (m/e): 542.2 (M+H+, 100%), 559.3 (M+NH4+, 60%).

Workup

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

Sources & evidence

ORD record
ord-16184fb7f75b405698b93a70ad5ff11a
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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