Reaktion #457077

Reaktionsgleichung

hydrochloride

2-[2-isopropyl-4-(3-carboxyacryloyl)phenoxymethylcarbonylamino]benzothiazole

4-(4-methyl-1-piperazinyl)piperidine

diethyl cyanophosphate

→

2-{2-isopropyl-4-[3-[4-(4-methyl-1-piperazinyl)-1-piperidinylcarbonyl]acryloyl]phenoxymethylcarbonylamino}benzothiazole dihydrochloride

Lösungsmittel

water

triethylamine

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture is extracted with ethyl acetate
2. 2
   WaschenThe extract is washed with water
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→10:1)
6. 6
   SonstigeThe compound thus obtained
7. 7
   Sonstigein ethanol by a conventional method, and recrystallized from ethanol-diethyl ether

Vorschrift

To a solution of 2-[2-isopropyl-4-(3-carboxyacryloyl)phenoxymethylcarbonylamino]benzothiazole (0.97 g) in dimethylformamide (10 ml) are added dropwise 4-(4-methyl-1-piperazinyl)piperidine (0.65 g) and diethyl cyanophosphate (0.6 ml) at room temperature. To the mixture is added triethylamine (0.5 ml), and the mixture is stirred at room temperature for 10 minutes. To the mixture is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→10:1). The compound thus obtained is converted into a hydrochloride thereof in ethanol by a conventional method, and recrystallized from ethanol-diethyl ether to give 2-{2-isopropyl-4-[3-[4-(4-methyl-1-piperazinyl)-1-piperidinylcarbonyl]acryloyl]phenoxymethylcarbonylamino}benzothiazole dihydrochloride (0.45 g).

Quelle