2-Isopropoxy-5-methylsulfonylbenzoic acid → (2-Isopropoxy-5-methanesulfonyl-phenyl)-{4-[5-(propane-2-sulfonyl)-thiazol-2-yl]-piperazin-1-yl}-methanone

HRID 1352333Notes

Reaction equation

HRID 1352333 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.[CH3:19][CH:20]([S:22]([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)(=[O:24])=[O:23])[CH3:21]>>[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]([N:33]1[CH2:34][CH2:35][N:30]([C:28]2[S:29][C:25]([S:22]([CH:20]([CH3:21])[CH3:19])(=[O:24])=[O:23])=[CH:26][N:27]=2)[CH2:31][CH2:32]1)=[O:9])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acidHCID 675498161-[5-(Propane-2-sulfonyl)-thiazol-2-yl]-piperazine hydrochloride

Product 1

HCID 58677830(2-Isopropoxy-5-methanesulfonyl-phenyl)-{4-[5-(propane-2-sulfonyl)-thiazol-2-yl]-piperazin-1-yl}-methanoneYield 67%

Procedure

Prepared in analogy to example 1 (b) from 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) and 1-[5-(propane-2-sulfonyl)-thiazol-2-yl]-piperazine hydrochloride. 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 67%). MS (m/e): 516.3 (M+H+, 100%), 533.3 (M+NH4+, 85%).

Workup

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

Sources & evidence

ORD record
ord-8e397d5a975d492898653553f87e5cb1
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

Loading…