Réaction #51959

Équation de réaction

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

1-(1,3-benzodioxol-5-yl)-2-(methylamino)ethanol

diisopropylethylamine

→

title compound

Rendement 72.9%

2-{[[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Rendement 72.9%

Solvants

DMF

water

Conditions de réaction

Traitement

1. 1
   TempératureAfter 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
   Lavagethe collected solid was washed with water
7. 7
   Autredried in vacuo
8. 8
   Autreleaving a white solid
9. 9
   AutreRecrystallization from acetonitrile (10 mL
10. 10
    workup.DISSOLUTIONdissolved
11. 11
    Températurewith warming
12. 12
    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-(1,3-benzodioxol-5-yl)-2-(methylamino)ethanol (Journal of Organometallic Chemistry, 1998, 339, 267-75) (74 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 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 a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (101 mg) as a white solid.

Source