Pyrazole → 4-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid [2-(4-(pyridin-4-yl)-piperazin-1-yl)ethyl]amide

HRID 2114310Notes

Reaction equation

HRID 2114310 reaction equation
N1C=C[CH:3]=N1.C[N:7]([C@@H:26]([C:28]1C=CC=CC=1)C)[C:8]([C:10]1[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[NH:12][N:11]=1)=[O:9].ClC1C=CC=CC=1C(Cl)=O.[N:44]1[CH:49]=[CH:48][C:47]([N:50]2[CH2:55][CH2:54][N:53](CCN)[CH2:52][CH2:51]2)=[CH:46][CH:45]=1>>[N:44]1[CH:49]=[CH:48][C:47]([N:50]2[CH2:51][CH2:52][N:53]([CH2:28][CH2:26][NH:7][C:8]([C:10]3[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])[N:12]([CH3:3])[N:11]=3)=[O:9])[CH2:54][CH2:55]2)=[CH:46][CH:45]=1

Participants

5

Reactant 4

HCID 1048PyrazoleHCID 691102-Chlorobenzoyl chlorideHCID 184406752-[4-(4-Pyridinyl)piperazino]ethylamineHCID 178461679HCID 178461679, compound

Product 1

HCID 597733384-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid [2-(4-(pyridin-4-yl)-piperazin-1-yl)ethyl]amide

Procedure

The pyrazole acid, prepared by coupling methyl ester 85 (Gen. Proc. 26) with 2-chlorobenzoyl chloride (21) followed by hydrolysis and bromination as shown in Gen. Proc. 8. was coupled to 2-(4-pyridin-4-yl-piperazin-1-yl)ethylamine (CA 985683) using the method of Procedure 10.

Workup

  1. customfollowed by hydrolysis and bromination

Sources & evidence

ORD record
ord-ddcc84bfbb784245bf475f8be3e372d8
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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