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

HRID 1352374Notes

Reaction equation

HRID 1352374 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.[F:22][C:23]([F:37])([F:36])[CH2:24][C:25]1[S:29][C:28]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:27][CH:26]=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:33]2[CH2:34][CH2:35][N:30]([C:28]3[S:29][C:25]([CH2:24][C:23]([F:37])([F:22])[F:36])=[CH:26][N:27]=3)[CH2:31][CH2:32]2)=[O:12])[CH:13]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211001791-[5-(2,2,2-Trifluoro-ethyl)-thiazol-2-yl]-piperazine hydrochlorideHCID 211003065-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid

Product 1

HCID 11592017[5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-{4-[5-(2,2,2-trifluoro-ethyl)-thiazol-2-yl]-piperazin-1-yl}-methanoneYield 32%

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-(2,2,2-trifluoro-ethyl)-thiazol-2-yl]-piperazine hydrochloride. The crude material was purified by chromatography (SiO2, methanol/dichloromethane) to yield the title compound as a white crystalline solid (yield 32%). MS (m/e): 546.3 (M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, methanol/dichloromethane)

Sources & evidence

ORD record
ord-fecb492f061848b198dedfaf0f795ca3
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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