反応 #3608

反応方程式

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

収率 39.5%

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

収率 39.5%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

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
   洗浄washed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   その他The reaction mixture is dried with Na2 SO4
7. 7
   ろ過filtered
8. 8
   その他evaporated in vacuo
9. 9
   その他to give a solid which
10. 10
    その他is purified by flash chromatography

実験手順

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.

出典