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

HRID 1352322Notes

Reaction equation

HRID 1352322 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].Cl.[CH2:22]([S:24]([C:27]1[S:31][C:30]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[N:29][CH:28]=1)(=[O:26])=[O:25])[CH3:23]>>[CH2:22]([S:24]([C:27]1[S:31][C:30]([N:32]2[CH2:33][CH2:34][N:35]([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][CH:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[O:12])[CH2:36][CH2:37]2)=[N:29][CH:28]=1)(=[O:26])=[O:25])[CH3:23]

Participants

3

Reactant 2

HCID 211001851-(5-Ethanesulfonyl-thiazol-2-yl)-piperazine hydrochlorideHCID 211003065-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid

Product 1

HCID 11548540[4-(5-Ethanesulfonyl-thiazol-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-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-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 61%). MS (m/e): 556.3 (M+H+, 100%), 573.3 (M+NH4+, 55%).

Workup

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

Sources & evidence

ORD record
ord-e9398141eb7a4c309b30aebffb0bf794
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

Loading…