1-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-piperazine dihydrochloride → {4-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-piperazin-1-yl}-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

HRID 1352288Notes

Reaction equation

HRID 1352288 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].Cl.Cl.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[C:28]1[N:29]=[C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[S:31][CH:32]=1>>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[C:28]1[N:29]=[C:30]([N:33]2[CH2:34][CH2:35][N:36]([C:7]([C:6]3[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:5]=3[O:4][CH:1]([CH3:2])[CH3:3])=[O:9])[CH2:37][CH2:38]2)[S:31][CH:32]=1

Participants

3

Reactant 2

HCID 211001731-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-piperazine dihydrochlorideHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 21100260{4-[4-(2,4-Dichloro-phenyl)-thiazol-2-yl]-piperazin-1-yl}-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 17%

Procedure

Prepared in analogy to example 1 (b) from 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) and 1-[4-(2,4-dichloro-phenyl)-thiazol-2-yl]-piperazine dihydrochloride. The crude material was purified by chromatography (SiO2, methanol/dichloromethane) (yield 17%). MS (m/e): 558.1 ({37Cl}M+H+, 19%), 555.9 ({37Cl35Cl}M+H+, 58%), 554.1 ({35Cl}M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, methanol/dichloromethane) (yield 17%)

Sources & evidence

ORD record
ord-1cdb12ce144f4bfca1eb44d35d762bb0
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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