Resorcinol → 2-chloro-5,11-dihydro-11-ethyl-8-(3-hydroxyphenyl)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724976
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1>CS(C)=O.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33][C:1]4[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=4)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1

Komponenten

6

Edukt 3

HCID 5054ResorcinolHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 159563382-chloro-5,11-dihydro-11-ethyl-8-(3-hydroxyphenyl)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Resorcinol (0.082 g, 0.74 mmol) in dimethyl sulfoxide (1 mL) was treated with potassium tert-butoxide (1.0M in tetrahydrofuran, 0.15 mL, 0.15 mmol). The resulting stirred solution was treated with 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.050 g, 0.14 mmol) in dimethyl sulfoxide (1 mL) and the mixture was stirred an additional 16 hours. The mixture was diluted with ethyl acetate (50 mL) washed with brine, water, and brine (15 mL each). The organics were dried over sodium sulfate, concentrated and the residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) followed by crystallization from hexanes to give the title compound (0.031 g, 51%), m.p. 219°-220° C.

Aufarbeitung

  1. stirringthe mixture was stirred an additional 16 hours
  2. washwashed with brine, water, and brine (15 mL each)
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient)
  6. customfollowed by crystallization from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7cd25f6d86a145dc94cc7ac0bae4962f
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705499

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