반응 #3608

반응 방정식

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

수율 39.5%

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

수율 39.5%

용매

methylene chloride

methylene chloride

반응 조건

후처리

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
   세척washed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   기타The reaction mixture is dried with Na2 SO4
7. 7
   여과filtered
8. 8
   기타evaporated in vacuo
9. 9
   기타to give a solid which
10. 10
    기타is purified by flash chromatography

실험 절차

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.

출처