2-Piperazin-1-yl-thiazole-5-carbonitrile → 2-{4-[5-Methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoyl]-piperazin-1-yl}-thiazole-5-carbonitrile

HRID 1352292Notes

Reaction equation

HRID 1352292 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].[N:20]1([C:26]2[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[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]([N:23]1[CH2:24][CH2:25][N:20]([C:26]2[S:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=2)[CH2:21][CH2:22]1)=[O:12])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211002572-Piperazin-1-yl-thiazole-5-carbonitrileHCID 211003125-Methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid

Product 1

HCID 211002172-{4-[5-Methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoyl]-piperazin-1-yl}-thiazole-5-carbonitrileYield 57%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid (Example A3) and 2-piperazin-1-yl-thiazole-5-carbonitrile (Example 6(a)). The crude material was purified by chromatography (SiO2, ethyl acetate/heptane) followed by trituration in ether to yield the title compound as a light brown crystalline solid (yield 57%). MS (m/e): 475.0 (M+H+, 100%), 492.3 (M+NH4+, 90%).

Workup

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

Sources & evidence

ORD record
ord-51053fc6461144148eb79e172ece4a01
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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