Réaction #51950

Équation de réaction

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

1-(1H-indol-3-yl)-2-(methylamino)ethanol

diisopropylethylamine

→

title compound

Rendement 81.6%

N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(1H-indol-3-yl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Rendement 81.6%

Solvants

DMF

water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting milky suspension was stirred vigorously for 30 minutes
2. 2
   workup.WAITleft
3. 3
   workup.WAITstanding overnight at room temp
4. 4
   FiltrationThe mixture was filtered
5. 5
   Lavagethe collected solid was washed with water
6. 6
   Autredried in vacuo
7. 7
   Autreleaving a white solid
8. 8
   AutreRecrystallization from acetonitrile (10 mL
9. 9
   workup.DISSOLUTIONdissolved
10. 10
    Températurewith warming
11. 11
    Températurecooled to 0° C. overnight)

Mode opératoire

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), 1-(1H-indol-3-yl)-2-(methylamino)ethanol (Khim.-Farm. Zh. 1970, 4, 5-9)(73 mg, 0.38 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5.0 mL) was stirred for 48 hours at 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 a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (112 mg) as a white solid.

Source