2-Piperazin-1-yl-thiazole-5-carbonitrile → 2-[4-(2-tert-Butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-thiazole-5-carbonitrile

HRID 1352301Notes

Reaction equation

HRID 1352301 reaction equation
[C:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:7]=1[C:8]([OH:10])=O)([CH3:4])([CH3:3])[CH3:2].[N:19]1([C:25]2[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[C:1]([O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:7]=1[C:8]([N:22]1[CH2:23][CH2:24][N:19]([C:25]2[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=2)[CH2:20][CH2:21]1)=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 211002572-Piperazin-1-yl-thiazole-5-carbonitrileHCID 211002592-tert-Butoxy-5-methanesulfonyl-benzoic acid

Product 1

HCID 211002152-[4-(2-tert-Butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-thiazole-5-carbonitrileYield 52%

Procedure

Prepared in analogy to example 1 (b) from 2-tert-butoxy-5-methanesulfonyl-benzoic acid (Example A12) 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 52%). MS (m/e): 449.3 (M+H+, 50%), 466.4 (M+NH4+, 100%).

Workup

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

Sources & evidence

ORD record
ord-e472beacd91e497f83db862d3753c838
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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