Triethylamine → N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]-3-chlorophenyl]-2,4-dichlorobenzamide

HRID 3609

Reaktionsgleichung

Reaktionsgleichung von HRID 3609
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:24])[CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36].[OH-].[Na+]>ClCCl>[CH:18]1[C:13]2[N:12]3[CH:19]=[CH:20][CH:21]=[C:11]3[CH2:10][CH2:9][N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][C:40]([Cl:42])=[CH:41][C:33]=4[Cl:32])=[CH:3][C:4]=3[Cl:24])=[O:7])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 666452,4-Dichlorobenzoyl chlorideHCID 218369946,7-Dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepin

Produkt 1

HCID 54410265N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl]-3-chlorophenyl]-2,4-dichlorobenzamideAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.10 g of 2,4-dichlorobenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred at room temperature for 2 hours and 2 ml of 1N NaOH is added. The volatiles are removed under vacuum and to the residue is added 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred at room temperature for 2 hours and the volatiles removed. To the residue is added 2 ml of 1N NaOH and 5 ml of H2O. The mixture is extracted with ethyl acetate and the extract washed with brine and dried (Na2SO4). The solvent is removed and the solid triturated with diethyl ether-hexane to give 0.15 g of white solid, Mass Spectrum (CI): 510(M+H, Cl35).

Aufarbeitung

  1. customThe volatiles are removed under vacuum and to the residue
  2. additionis added 2 ml of tetrahydrofuran and 1 ml of methanol
  3. stirringThe mixture is stirred at room temperature for 2 hours
  4. customthe volatiles removed
  5. additionTo the residue is added 2 ml of 1N NaOH and 5 ml of H2O
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe extract washed with brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed
  10. customthe solid triturated with diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-11dd793ef6d44dfb954c77ff0c37036a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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