Triethylamine → N-(2,3-Dimethylphenyl)-4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)benzamide

HRID 1459549

Reaktionsgleichung

Reaktionsgleichung von HRID 1459549
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.C(N(CC)CC)C.Cl.[CH3:34][C:35]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:36]=1[NH2:37].C(P(C#N)(CC)=O)C>ClCCl>[CH3:34][C:35]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:36]=1[NH:37][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 99056284-(5H-pyrrolo[2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acidHCID 13586794DiethylphosphorylcyanideHCID 22239262Benzenamine, ar,ar-dimethyl-, hydrochloride (1:1)

Produkt 1

HCID 21837120N-(2,3-Dimethylphenyl)-4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)benzamideAusbeute 25,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.332 g of 4-(5H-pyrrolo[2,1-c]-[1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acid, 0.222 g of triethylamine, 0.157 g of 2,3-dimethylaniline hydrochloride, 0.15 ml of diethylphosphoryl cyanide in 20 ml of dichloromethane is heated on a steam bath for 3 hours. The mixture is washed with H2O, 1M NaHCO3, H2O, 1N HCl, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated to dryness under vacuum and the residue crystallized from dichloromethane-hexane to give 0.11 g of crystals, m.p. 239°-240° C.

Aufarbeitung

  1. temperatureis heated on a steam bath for 3 hours
  2. washThe mixture is washed with H2O, 1M NaHCO3, H2O, 1N HCl, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe filter cake washed with dichloromethane
  6. concentrationThe filtrate is concentrated to dryness under vacuum
  7. customthe residue crystallized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c162532d97c94fa1b08f84c650e7a90c
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05854237

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