تفاعل #51942

معادلة التفاعل

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

المردود 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

المردود 50.4%

المذيبات

DMF

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter 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
   ترشيحThe mixture was filtered
6. 6
   غسيلthe collected solid was washed with water
7. 7
   أخرىdried in vacuo
8. 8
   أخرىleaving a white solid
9. 9
   أخرىRecrystallization from acetonitrile (30 mL
10. 10
    workup.DISSOLUTIONdissolved
11. 11
    درجة الحرارةwith warming
12. 12
    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), 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.

المصدر