Reaktion #10188

Reaktionsgleichung

methanol CH2Cl2

HOAc

ethoxymethylenemalononitrile

4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester

→

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Einengenconcentrated
3. 3
   workup.ADDITIONtreated with H2O and saturated aqueous Na2CO3 solution
4. 4
   Extraktionthen extracted with ethyl acetate (3×50 mL)
5. 5
   Trocknendried (Na2SO4)
6. 6
   FiltrationAfter filtration and concentration
7. 7
   Sonstigethe residue was chromatographed
8. 8
   Sonstigeto provide a yellow oil

Vorschrift

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).

Quelle