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

HRID 975900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975900
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32](Cl)=[O:33].C(N(CC)CC)C>ClCCl>[CH:23]1[CH:22]=[CH:21][N:13]2[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[CH2:31][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH3:24])=[N:7][CH:6]=3)=[O:9])[CH2:11][C:12]=12

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2760632o-Tolyl-acetyl chlorideHCID 1891750110, 11-dihydro-10-(6-amino-3-pyridinylcarbonyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 18917528N-[5-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)-2-pyridinyl]-2-methylbenzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2.0 mmol of 10,11-dihydro-10-(6-amino-3-pyridinylcarbonyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 2.1 mmol of 2-methylbenzeneacetyl chloride and 5 mmol of triethylamine in 10 ml of dichloromethane is stirred under argon at room temperature for 16 hours. The solvent is removed under vacuum and the residue partitioned between 50 ml of ethyl acetate and 25 ml of water. The organic layer is separated, washed with H2O, 1N NaHCO3, brine and dried (Na2SO4). The solvent is removed and the residue chromatographed on silica gel with ethyl acetate-hexane as solvent to give the product as a solid.

Aufarbeitung

  1. customThe solvent is removed under vacuum
  2. customthe residue partitioned between 50 ml of ethyl acetate and 25 ml of water
  3. customThe organic layer is separated
  4. washwashed with H2O, 1N NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed
  7. customthe residue chromatographed on silica gel with ethyl acetate-hexane as solvent

Quellen und Nachweise

ORD-Eintrag
ord-6cadaa4dfa704298b42cced2a8c51fa9
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610156

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