1-(5-Trifluoromethyl-thiazol-2-yl)-piperazine hydrochloride → [5-Methanesulfonyl-2-(1-trifluoromethyl-propoxy)-phenyl]-[4-(5-trifluoromethyl-thiazol-2-yl)-piperazin-1-yl]-methanone

HRID 1352381Notes

Reaction equation

HRID 1352381 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH:15]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH3:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].Cl.[F:23][C:24]([F:37])([F:36])[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]([C:18]([F:21])([F:20])[F:19])[CH2:16][CH3:17])=[C:9]([C:10]([N:33]2[CH2:34][CH2:35][N:30]([C:28]3[S:29][C:25]([C:24]([F:37])([F:23])[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 211002001-(5-Trifluoromethyl-thiazol-2-yl)-piperazine hydrochlorideHCID 211003025-Methanesulfonyl-2-(1-trifluoromethyl-propoxy)-benzoic acid

Product 1

HCID 21100303[5-Methanesulfonyl-2-(1-trifluoromethyl-propoxy)-phenyl]-[4-(5-trifluoromethyl-thiazol-2-yl)-piperazin-1-yl]-methanoneYield 11%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(1-trifluoromethyl-propoxy)-benzoic acid (Example A19) and 1-(5-trifluoromethyl-thiazol-2-yl)-piperazine hydrochloride (Example 58(c)). The crude material was purified by reversed phase HPLC (acetonitrile/water) followed by trituration in ether to yield the title compound as an off-white crystalline solid (yield 11%). MS (m/e): 546.3 (M+H+, 100%).

Workup

  1. customThe crude material was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-763d240508f043458fa18b4f6beb67a5
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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