Reacción #75755

Ecuación de reacción

phenyl isocyanate

4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butaneamine

→

N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N′-phenylurea

Rendimiento 57.9%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAminomethyl resin (280 mg of 1% cross linked, 100-200 mesh available from BACHEM, Torrance, Calif.) was added
2. 2
   workup.STIRRINGto stir for 0.5 hr
3. 3
   workup.ADDITIONSilica gel (0.4 g) was added
4. 4
   Concentraciónthe mixture was concentrated under vacuum
5. 5
   Otroto provide a solid
6. 6
   OtroThe solid was purified by flash chromatography
7. 7
   Lavadoeluting with 95/5 dichloromethane/methanol
8. 8
   Otroto give a white solid which
9. 9
   Otrowas dried under vacuum at 60° C.

Procedimiento

Under a nitrogen atmosphere, phenyl isocyanate (52 μL, 0.48 mmol) was added to a suspension of 4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butaneamine (0.15 g, 0.48 mmole) in anhydrous tetrahydrofuran (60 mL). The reaction mixture was stirred for 20 minutes at which time it had turned homogeneous and thin layer chromatography indicated no starting material remained. Aminomethyl resin (280 mg of 1% cross linked, 100-200 mesh available from BACHEM, Torrance, Calif.) was added and the reaction mixture was allowed to stir for 0.5 hr. Silica gel (0.4 g) was added and the mixture was concentrated under vacuum to provide a solid. The solid was purified by flash chromatography eluting with 95/5 dichloromethane/methanol to give a white solid which was dried under vacuum at 60° C. to provide 0.12 g of N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N′-phenylurea. Analysis: Calculated for C24H29N7O+⅕H2O: %C, 66.25; %H, 6.81; %N, 22.53. Found: %C, 66.27; %H, 6.63; %N, 22.83

Fuente