Реакция #3608

Уравнение реакции

3-methylbenzo[b]thiophene-2-acetyl chloride

triethylamine

dimethylaminopyridine

3-methylbenzo[b]thiophene-2-acetyl chloride

triethylamine

10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

→

desired product

Выход 39.5%

N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methylbenzo[b]thiophene-2-acetamide

Выход 39.5%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 hours at room temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for an additional 18 hours
5. 5
   Промывкаwashed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   ДругоеThe reaction mixture is dried with Na2 SO4
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated in vacuo
9. 9
   Другоеto give a solid which
10. 10
    Другоеis purified by flash chromatography

Методика

To a stirred solution of 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride in 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. An additional 0.445 g of 3-methylbenzo[b]thiophene-2-acetyl chloride, 0.346 g of triethylamine and 30 mg of dimethylaminopyridine is added and stirring continued for an additional 18 hours. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, 1M NaHCO3, and brine. The reaction mixture is dried with Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give 0.320 g of the desired product as a yellow foam.

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