Reaktion #80218

ord-f108833a008d40198b6dd520f665101f

Reaktionsgleichung

On1nnc2ccccc21
1-hydroxybenzotriazole
O=C(O)c1cnc2cc(NC(=O)c3ccccc3-c3ccc(C(F)(F)F)cc3)ccc2c1
7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acid
NCc1ccc(Cl)cc1
4-chlorobenzylamine
CCN(CC)CC
triethylamine
CCN=C=NCCCN(C)C.Cl
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
O=C(NCc1ccc(Cl)cc1)c1cnc2cc(NC(=O)c3ccccc3-c3ccc(C(F)(F)F)cc3)ccc2c1
title compound
O=C(NCc1ccc(Cl)cc1)c1cnc2cc(NC(=O)c3ccccc3-c3ccc(C(F)(F)F)cc3)ccc2c1
7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid 4-chloro-benzylamide

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenthe reaction mixture was concentrated
  2. 2
    Filtrationthe solid was collected by vacuum filtration
  3. 3
    Filtrationthe solid collected by vacuum filtration

Vorschrift

7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acid (40 mg, 0.092 mmol) was combined with 4-chlorobenzylamine (19 mg, 0.14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21 mg, 0.11 mmol), 1-hydroxybenzotriazole (14 mg, 0.10 mmol), and triethylamine (0.051 ml, 0.37 mmol) in 1.5 ml of dichloromethane. After stirring overnight at ambient temperature, the reaction mixture was concentrated, the residue was suspended in water, and the solid was collected by vacuum filtration. This material was then slurried in a 1:1 methanol-dichloromethane solution, and the solid collected by vacuum filtration to afford the title compound as a colorless solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713489B2uspto-grants-2004_03