3-(3-Chlorophenyl)-2-propynoic acid → 3-(3-chlorophenyl)-N-(2-(methyl(thiazol-5-yl)amino)ethyl)propiolamide

HRID 1677097Notes

Reaction equation

HRID 1677097 reaction equation
N=C=N.[CH3:4][N:5]([C:9]1[S:13][CH:12]=[N:11][CH:10]=1)[CH2:6][CH2:7][NH2:8].[Cl:14][C:15]1[CH:16]=[C:17]([C:21]#[C:22][C:23](O)=[O:24])[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]([C:21]#[C:22][C:23]([NH:8][CH2:7][CH2:6][N:5]([CH3:4])[C:9]2[S:13][CH:12]=[N:11][CH:10]=2)=[O:24])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 238793-(3-Chlorophenyl)-2-propynoic acidHCID 160435CarbodiimideHCID 69129233N1-methyl-N1-(thiazol-5-yl)ethane-1,2-diamine

Product 1

HCID 598266893-(3-chlorophenyl)-N-(2-(methyl(thiazol-5-yl)amino)ethyl)propiolamideYield 21.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g (≅1.8 mmol) PS carbodiimide was added to a solution of 146 mg (0.93 mmol) N1-methyl-N1-(thiazol-5-yl)ethane-1,2-diamine and 252 mg (1.39 mmol) 3-(3-chlorophenyl)propiolic acid in DCM (10 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 10:1) was performed with the residue, whereby 63 mg (0.20 mmol, 21%) 3-(3-chlorophenyl)-N-(2-(methyl(thiazol-5-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-eccefa55208341f894010cfc5c55b414
Source dataset
uspto-grants-2011_08
Patent number
US08008304B2

Reaction notes

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