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

HRID 3491

Reaktionsgleichung

Reaktionsgleichung von HRID 3491
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].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.C(OCC)(=O)C>[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:4](=[O:5])[C:3]4[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=4[Cl:1])=[CH:41][CH:40]=3)=[O:25])[CH2:27][C:28]=12

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 9826254N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)-phenyl]2,4-dichlorobenzamideAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 415 mg of 2,4-dichlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 18 hours. The volatiles are concentrated in vacuo to give a residue which is dissolved in ethyl acetate, washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4, filtered and concentrated in vacuo to give a residue which is crystallized from ethyl acetate to give 420 mg of the desired product as a crystalline solid, m.p., 210°-212° C.

Aufarbeitung

  1. customThe bath is removed
  2. stirringthe reaction mixture stirred at room temperature for 18 hours
  3. concentrationThe volatiles are concentrated in vacuo
  4. customto give a residue which
  5. washwashed with water, 2N citric acid, 1M NaHCO3 and brine
  6. dry with materialThe organic layer is dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a residue which
  10. customis crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-35f83a206245410e867603ca398e5466
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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