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

HRID 55138

Reaktionsgleichung

Reaktionsgleichung von HRID 55138
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].C(N(CC)CC)C.[NH2:19][C:20]1[CH:41]=[CH:40][C:23]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][N:29]3[CH:37]=[CH:38][CH:39]=[C:28]3[CH2:27]2)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl>[CH:39]1[CH:38]=[CH:37][N:29]2[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:26]([C:24]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:5](=[O:6])[C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[O:2][CH3:1])=[CH:41][CH:40]=3)=[O:25])[CH2:27][C:28]=12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 10789117N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-methoxybenzamideAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 0.362 g of 2-methoxybenzoyl chloride 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. 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 through hydrous magnesium silicate and evaporated in vacuo to give a solid which is purified by crystallization from ethyl acetate to give 0.430 g of the desired product as a crystalline solid, m.p. 185°-188° C.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 18 hours at room temperature
  3. washwashed with water, 2N citric acid, 1M NaHCO3, and brine
  4. dry with materialThe reaction mixture is dried with Na2SO4
  5. filtrationfiltered through hydrous magnesium silicate
  6. customevaporated in vacuo
  7. customto give a solid which
  8. customis purified by crystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e81c778e12ec40c4bb6c28cb5dd723a3
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624923

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