Reaktion #51969

Reaktionsgleichung

N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

2-(methylamino)ethanol

diisopropylethylamine

→

title compound

Ausbeute 97.7%

N-(4-chlorobenzyl)-2-{[(2-hydroxyethyl)(methyl)-amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Ausbeute 97.7%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   workup.STIRRINGThe resulting milky suspension was stirred vigorously for 30 minutes
3. 3
   workup.WAITleft
4. 4
   workup.WAITstanding overnight at room temp
5. 5
   FiltrationThe mixture was filtered
6. 6
   Waschenthe collected solid was washed with water
7. 7
   Sonstigedried in vacuo

Vorschrift

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.25 mmol), 2-(methylamino)ethanol (40 mg, 0.53 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 7 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving the title compound (106 mg) as a white solid.

Quelle