Pyrazole → Ethylenediamine

HRID 2114312Notes

Reaction equation

HRID 2114312 reaction equation
[NH:1]1[CH:5]=CC=N1.C[N:7]([C@@H:26](C1C=CC=CC=1)[CH3:27])[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].Cl[C:35]1C=[CH:42][CH:41]=[CH:40][C:36]=1C(Cl)=O.N[CH2:45]CC1C=CC(C#N)=CC=1>>[CH2:10]([NH2:11])[CH2:8][NH2:7].[CH3:5][N:1]1[CH2:42][CH2:41][CH:40]([CH2:27][CH2:26][NH:7][C:8]([C:10]2[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:12]([CH3:45])[N:11]=2)=[O:9])[CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 691102-Chlorobenzoyl chlorideHCID 219125254-(2-Aminoethyl)benzonitrileHCID 178461679HCID 178461679, compound

Product 2

HCID 3301EthylenediamineHCID 597735024-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid [2-(n-methyl-piperidin-4-yl)-ethyl]amide

Procedure

The pyrazole acid, prepared by coupling methyl ester 85 (Procedure 26) with 2-chlorobenzoyl chloride (21) followed by hydrolysis and bromination as shown in Procedure 8, was coupled to amine 169 (Procedure 34) using the method of Procedure 10. Formation of the amidine using the method of Procedure 33 using ethylene diamine afforded the title compound.

Workup

  1. customfollowed by hydrolysis and bromination

Sources & evidence

ORD record
ord-b9336c3ccaec44958ecafe2ee00a4297
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

Loading…