Reacción #51950

Ecuación de reacción

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

Rendimiento 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

Rendimiento 81.6%

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

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
   FiltraciónThe mixture was filtered
5. 5
   Lavadothe collected solid was washed with water
6. 6
   Otrodried in vacuo
7. 7
   Otroleaving a white solid
8. 8
   OtroRecrystallization from acetonitrile (10 mL
9. 9
   workup.DISSOLUTIONdissolved
10. 10
    Temperaturawith warming
11. 11
    Temperaturacooled to 0° C. overnight)

Procedimiento

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.

Fuente