Reaktion #3608

Reaktionsgleichung

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

Ausbeute 39.5%

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

Ausbeute 39.5%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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
   Waschenwashed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   SonstigeThe reaction mixture is dried with Na2 SO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated in vacuo
9. 9
   Sonstigeto give a solid which
10. 10
    Sonstigeis purified by flash chromatography

Vorschrift

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.

Quelle