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

HRID 1352291Notes

Reaction equation

HRID 1352291 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].[N:21]1([C:27]2[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]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]([CH:13]=1)[C:10]([N:24]1[CH2:25][CH2:26][N:21]([C:27]2[S:28][C:29]([C:32]#[N:33])=[CH:30][N:31]=2)[CH2:22][CH2:23]1)=[O:12])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 211002572-Piperazin-1-yl-thiazole-5-carbonitrileHCID 211003065-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid

Product 1

HCID 115332362-{4-[5-Methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-thiazole-5-carbonitrileYield 59%

Procedure

Prepared in analogy to example 1 (b) from 5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example A2) 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 white crystalline solid (yield 59%). MS (m/e): 489.1 (M+H+, 100%), 506.1 (M+NH4+, 78%).

Workup

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

Sources & evidence

ORD record
ord-2954417be50c4e17a63c0f76fc26d9f0
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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