Acetic Acid → 7-Butyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([NH2:25])[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26]C(O)=O.C(OC=C(C#N)C#N)C.CO.C(Cl)Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:19][CH:17]([C:16]3[CH:15]=[C:14]4[C:13](=[CH:12][C:11]=32)[N:25]=[CH:26][N:20]4[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (440 mg, 1.27 mmol) was dissolved in ethanol (20 mL) and HOAc (2 mL) and treated with ethoxymethylenemalononitrile (186 mg, 1.52 mmol). The resulting mixture was warmed to 60° C. and stirred 18 hours. The reaction was cooled, concentrated, treated with H2O and saturated aqueous Na2CO3 solution then extracted with ethyl acetate (3×50 mL) and dried (Na2SO4). After filtration and concentration, the residue was chromatographed to provide a yellow oil. (400 mg, 89%). (TLC 5% methanol/CH2Cl2 (NH3) Rf 0.70).
Aufarbeitung
- temperatureThe reaction was cooled
- concentrationconcentrated
- additiontreated with H2O and saturated aqueous Na2CO3 solution
- extractionthen extracted with ethyl acetate (3×50 mL)
- dry with materialdried (Na2SO4)
- filtrationAfter filtration and concentration
- customthe residue was chromatographed
- customto provide a yellow oil
Quellen und Nachweise
- ORD-Eintrag
- ord-68ea851bb95b437fb81cc4da47dceaf5
- Quelldatensatz
- uspto-grants-2007_04
- Patentnummer
- US07205300B2
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