تفاعل #51950

معادلة التفاعل

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

المردود 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

المردود 81.6%

المذيبات

DMF

water

ظروف التفاعل

المعالجة

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
   ترشيحThe mixture was filtered
5. 5
   غسيلthe collected solid was washed with water
6. 6
   أخرىdried in vacuo
7. 7
   أخرىleaving a white solid
8. 8
   أخرىRecrystallization from acetonitrile (10 mL
9. 9
   workup.DISSOLUTIONdissolved
10. 10
    درجة الحرارةwith warming
11. 11
    درجة الحرارةcooled to 0° C. overnight)

الإجراء التجريبي

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.

المصدر