Water → N-[4-(6,11-Dihydropyrido[2,3-b][1,5]benzodiazepin-6(5H)-ylcarbonyl)-3-chlorophenyl][1,1'-biphenyl]-2-carboxamide

HRID 1457699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457699
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:16]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:17]([C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[C:27]([Cl:34])[CH:26]=2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.O>ClCCl>[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:29]([C:28]3[CH:32]=[CH:33][C:25]([NH:24][C:22]([C:17]4[C:16]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:23])=[CH:26][C:27]=3[Cl:34])=[O:30])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 220996004-[([1,1'-Biphenyl]-2-carbonyl)amino]-2-chlorobenzoyl chloride

Produkt 1

HCID 22099880N-[4-(6,11-Dihydropyrido[2,3-b][1,5]benzodiazepin-6(5H)-ylcarbonyl)-3-chlorophenyl][1,1'-biphenyl]-2-carboxamideAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.197 g of 6,11-dihydropyrido[2,3-b][1,5]benzodiazepine, 0.444 g of 4-[([1,1'-biphenyl]-2-carbonyl)amino]-2-chlorobenzoyl chloride and 0.155 g of N,N-diisopropylethylamine in 8 ml of dichloromethane is stirred at room temperature for 1.5 hours. The mixture is poured into water and extracted with dichloromethane. The extract is washed with H2O, saturated NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates with hexane-ethyl acetate (1:2) to give 0.160 g of solid, m.p. 147° C.-165° C. Anal Found: C, 72.1; H, 5.1; N, 9.1; Cl, 6.3.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with H2O, saturated NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue is chromatographed on thick layer silica gel plates with hexane-ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-8c6d6099666b4beb8d7db81577d9608d
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849735

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