Reacción #51942

Ecuación de reacción

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

2-(methylamino)-1-(3,4,5-trifluorophenyl)ethanol

diisopropylethylamine

→

title compound

Rendimiento 50.4%

N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(3,4,5-trifluorophenyl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Rendimiento 50.4%

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter 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
   FiltraciónThe mixture was filtered
6. 6
   Lavadothe collected solid was washed with water
7. 7
   Otrodried in vacuo
8. 8
   Otroleaving a white solid
9. 9
   OtroRecrystallization from acetonitrile (30 mL
10. 10
    workup.DISSOLUTIONdissolved
11. 11
    Temperaturawith warming
12. 12
    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), 2-(methylamino)-1-(3,4,5-trifluorophenyl)ethanol (Preparation 46)(77 mg, 0.38 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 6 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 a white solid. Recrystallization from acetonitrile (30 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (71 mg) as a white solid.

Fuente