2,4-Dichlorobenzoyl chloride → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl]-2-methylphenyl]-2,4-dichlorobenzamide

HRID 3564

Reaktionsgleichung

Reaktionsgleichung von HRID 3564
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[NH2:24])[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][N:10]2[CH:18]=[CH:19][CH:20]=[C:9]2[CH2:8]1)=[O:6].[Cl:25][C:26]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].C(N(C(C)C)CC)(C)C>ClCCl>[CH:20]1[CH:19]=[CH:18][N:10]2[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([C:5]([C:4]3[CH:21]=[CH:22][C:23]([NH:24][C:28](=[O:29])[C:27]4[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:26]=4[Cl:25])=[C:2]([CH3:1])[CH:3]=3)=[O:6])[CH2:8][C:9]=12

Komponenten

5

Edukt 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 1068697510,11-Dihydro-10-(4-amino-3-methylbenzoyl)-5H-Pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 10743659N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl]-2-methylphenyl]-2,4-dichlorobenzamideAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.40 g of 10,11-dihydro-10-(3-methyl-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.40 g of 2,4-dichlorobenzoyl chloride and 0.75 g of diisopropylethylamine in 50 ml of dichloromethane is stirred at room temperature for 16 hours. The mixture is washed with water, dried (MgSO4) and the solution passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and hexane added to give crystals. Recrystallization from dichloromethane-hexane gives 0.52 g of crystals, m.p. 213°-215° C.

Aufarbeitung

  1. washThe mixture is washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationThe filtrate is concentrated
  4. additionhexane added
  5. customto give crystals
  6. customRecrystallization from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f0f4f088cd0d48ca83f5762cc569ed4f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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