Reaktion #426205

Reaktionsgleichung

DIEA

2,8-dimethylquinoline-7-carboxylic acid

isopropylamine

HATU

HCl

→

N-isopropyl-2,8-dimethylquinoline-7-carboxamide

Ausbeute 93.0%

Lösungsmittel

water

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe combined organic extracts were washed with water and brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by reverse phase chromatography (Biotage SP4, 25M C-18, 5-60% MeCN—H2O)

Vorschrift

A mixture of 2,8-dimethylquinoline-7-carboxylic acid (0.20 g, 0.994 mmol), isopropylamine (0.102 mL, 1.19 mmol) and HATU (0.491 g, 1.29 mmol) in anhydrous MeCN (5 mL) under a nitrogen atmosphere was cooled to 0° C. in an ice bath. To the cooled mixture was added dropwise DIEA (0.69 mL, 3.98 mmol) and the resulting mixture stirred at ambient temperature for 18 hours. The mixture was diluted with water, neutralized with aqueous 1N HCl and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (Biotage SP4, 25M C-18, 5-60% MeCN—H2O) to afford N-isopropyl-2,8-dimethylquinoline-7-carboxamide (0.223 g, 93%).

Quelle