1-(5-Ethanesulfonyl-thiazol-2-yl)-piperazine hydrochloride → [4-(5-Ethanesulfonyl-thiazol-2-yl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone

HRID 1352318Notes

Reaction equation

HRID 1352318 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.[CH2:19]([S:21]([C:24]1[S:28][C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[N:26][CH:25]=1)(=[O:23])=[O:22])[CH3:20]>>[CH2:19]([S:21]([C:24]1[S:28][C:27]([N:29]2[CH2:30][CH2:31][N:32]([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])[CH2:33][CH2:34]2)=[N:26][CH:25]=1)(=[O:23])=[O:22])[CH3:20]

Participants

3

Reactant 2

HCID 211001851-(5-Ethanesulfonyl-thiazol-2-yl)-piperazine hydrochlorideHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 21100274[4-(5-Ethanesulfonyl-thiazol-2-yl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanoneYield 71%

Procedure

Prepared in analogy to example 1 (b) from 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) and 1-(5-ethanesulfonyl-thiazol-2-yl)-piperazine hydrochloride (Example 32(c)). 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 71%). MS (m/e): 502.3 (M+H+, 100%), 519.3 (M+NH4+, 82%).

Workup

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

Sources & evidence

ORD record
ord-fcb3e2a71d644f058b747327ea50f401
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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