Reaktion #80227

ord-b4f22c5ba3ce4586adf6677244390434

Reaktionsgleichung

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
CCN(CC)CC
triethylamine
CCN=C=NCCCN(C)C.Cl
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
On1nnc2ccccc21
1-hydroxybenzotriazole
COc1cccc(CN)c1
3-methoxybenzylamine
COc1cccc(CNC(=O)c2cnc3cc(NC(=O)c4ccccc4-c4ccc(C(F)(F)F)cc4)ccc3c2)c1
title compound
Ausbeute 86.7%
COc1cccc(CNC(=O)c2cnc3cc(NC(=O)c4ccccc4-c4ccc(C(F)(F)F)cc4)ccc3c2)c1
7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid 3-methoxy-benzylamide
Ausbeute 86.7%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenthe organic phase washed sequentially with water, and brine
  2. 2
    Trocknendried over anhydrous magnesium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated under vacuum

Vorschrift

7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (50 mg, 0.11 mmol) was combined with 3-methoxybenzylamine (16 mg, 0.11 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 0.14 mmol), 1-hydroxybenzotriazole (17 mg, 0.13 mmol), and triethylamine (0.064 ml, 0.46 mmol) in 1 ml of dichloromethane. After stirring overnight at ambient temperature, the reaction mixture was diluted with 30 ml of ethyl acetate, and the organic phase washed sequentially with water, and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to afford 53 mg of the title compound as a colorless solid.

Quelle

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