3-(3-Chlorophenyl)-2-propynoic acid → 3-(3-chlorophenyl)-N-(2-(methyl(1-methyl-1H-imidazol-2-yl)amino)ethyl)-propiolamide

HRID 1677098Notes

Reaction equation

HRID 1677098 reaction equation
N=C=N.[CH3:4][N:5]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1)[CH2:6][CH2:7][NH2:8].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=1>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:24]([NH:8][CH2:7][CH2:6][N:5]([CH3:4])[C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)=[O:25])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 238793-(3-Chlorophenyl)-2-propynoic acidHCID 160435CarbodiimideHCID 62592989N1-methyl-N1-(1-methyl-1H-imidazol-2-yl)ethane-1,2-diamine

Product 1

HCID 598266913-(3-chlorophenyl)-N-(2-(methyl(1-methyl-1H-imidazol-2-yl)amino)ethyl)-propiolamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.3 g (≅2.8 mmol) PS carbodiimide was added to a solution of 215 mg (1.4 mmol) N1-methyl-N1-(1-methyl-1H-imidazol-2-yl)ethane-1,2-diamine and 378 mg (2.1 mmol) 3-(3-chloro-phenyl)propiolic acid in DCM (30 ml) and the reaction solution was shaken for 16 h at RT. The resin was subsequently filtered off, washed with DCM and ethanol and the filtrate concentrated in a vacuum. CC (DCE/EtOH 5:1) was performed with the residue, whereby 241 mg (0.8 mmol, 54%) 3-(3-chlorophenyl)-N-(2-(methyl(1-methyl-1H-imidazol-2-yl)amino)ethyl)-propiolamide was obtained.

Workup

  1. filtrationThe resin was subsequently filtered off
  2. washwashed with DCM and ethanol
  3. concentrationthe filtrate concentrated in a vacuum

Sources & evidence

ORD record
ord-e8ef12e3b61a4f048a3e351b8f8e81b7
Source dataset
uspto-grants-2011_08
Patent number
US08008304B2

Reaction notes

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