反応 #51942

反応方程式

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

収率 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

収率 50.4%

溶媒

DMF

water

反応条件

後処理

1. 1
   温度After 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
   ろ過The mixture was filtered
6. 6
   洗浄the collected solid was washed with water
7. 7
   その他dried in vacuo
8. 8
   その他leaving a white solid
9. 9
   その他Recrystallization from acetonitrile (30 mL
10. 10
    workup.DISSOLUTIONdissolved
11. 11
    温度with warming
12. 12
    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), 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.

出典