反応 #51950

反応方程式

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

収率 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

収率 81.6%

溶媒

DMF

water

反応条件

後処理

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
   ろ過The mixture was filtered
5. 5
   洗浄the collected solid was washed with water
6. 6
   その他dried in vacuo
7. 7
   その他leaving a white solid
8. 8
   その他Recrystallization from acetonitrile (10 mL
9. 9
   workup.DISSOLUTIONdissolved
10. 10
    温度with warming
11. 11
    温度cooled to 0° C. overnight)

実験手順

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.

出典