反応 #3610

反応方程式

4-chloro-2-methoxybenzoyl chloride

triethylamine

4-chloro-2-methoxybenzoyl chloride

triethylamine

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

→

desired product

収率 41.1%

N-[4-(5H-Pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)ylcarbonyl)phenyl]-4-chloro-2-methoxybenzamide

収率 41.1%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 18 hours at room temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITis continued for 2 hours
5. 5
   洗浄washed with water, 2N citric acid, 1M NaHCO3, and brine
6. 6
   乾燥The reaction mixture is dried with Na2SO4
7. 7
   ろ過filtered
8. 8
   その他evaporated in vacuo
9. 9
   その他to give a residue which
10. 10
    その他is purified by flash chromatography
11. 11
    その他to give a solid which
12. 12
    その他is crystallized from ethyl acetate

実験手順

To a stirred solution of 0.406 g of 4-chloro-2-methoxybenzoyl 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 18 hours at room temperature. An additional 0.406 g of 4-chloro-2-methoxybenzoyl chloride and 0.346 g of triethylamine is added and stirring is continued for 2 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 Na2SO4, filtered and evaporated in vacuo to give a residue which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl acetate to give 0.320 g of the desired product as a white crystals, m.p. 222°-224° C.

出典