[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetic acid → 4-chloro-N-(4-{2-[4-(4,5-dihydro-thiazol-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-benzamide

HRID 2237532Notes

Reaction equation

HRID 2237532 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([OH:17])=O)[N:13]=2)=[O:7])=[CH:4][CH:3]=1.Cl.Cl.[N:22]1([C:28]2[S:29][CH2:30][CH2:31][N:32]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([N:25]3[CH2:26][CH2:27][N:22]([C:28]4[S:29][CH2:30][CH2:31][N:32]=4)[CH2:23][CH2:24]3)=[O:17])[N:13]=2)=[O:7])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 677042[2-(4-Chloro-benzoylamino)-thiazol-4-yl]-acetic acidHCID 686808382-(Piperazino)-2-thiazoline dihydrochloride

Product 1

HCID 596988454-chloro-N-(4-{2-[4-(4,5-dihydro-thiazol-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-benzamide

Procedure

In analogy to example 1.3, [2-(4-chloro-benzoylamino)-thiazol-4-yl]-acetic acid (example 1.2) was coupled with 2-(piperazino)-2-thiazoline dihydrochloride to give 4-chloro-N-(4-{2-[4-(4,5-dihydro-thiazol-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-benzamide, using general procedure C. White solid. MS 450.0 ([M+H]+)

Sources & evidence

ORD record
ord-978581d44e6842b1ba27093c9fbfa94e
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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