반응 #75753

반응 방정식

trimethyl orthovalerate

1,1-dimethylethyl N-{4-[(3-amino[1,5]naphthyridin-4-yl)amino]butyl}carbamate

p-Toluenesulfonic anhydride monohydrate

→

1,1-dimethylethyl N-[4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate

용매

xylene

ethyl acetate

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux overnight
3. 3
   세척washed with aqueous sodium bicarbonate
4. 4
   농축The organic layer was concentrated under vacuum
5. 5
   기타to provide an oily residue
6. 6
   기타The residue was triturated with hexane
7. 7
   기타to provide a dark pink solid
8. 8
   기타This solid was recrystallized from acetonitrile

실험 절차

Freshly distilled trimethyl orthovalerate (41 mL, 0.24 mole) was added to a mixture of 1,1-dimethylethyl N-{4-[(3-amino[1,5]naphthyridin-4-yl)amino]butyl}carbamate (39 g, 0.12 mole) in warm xylene (500 mL). The reaction mixture was heated at reflux overnight. Thin layer chromatography showed that at least half of the starting material was still present. p-Toluenesulfonic anhydride monohydrate (6 g) was added. After a short time thin layer chromatography showed that the reaction was complete. The reaction mixture was allowed to cool to ambient temperature and then it was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was concentrated under vacuum to provide an oily residue. The residue was triturated with hexane to provide a dark pink solid. This solid was recrystallized from acetonitrile to provide 1,1-dimethylethyl N-[4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate as a pale peach solid, m.p. 96.0-98.0° C. Analysis: Calculated for C22H31N5O2: %C, 66.47; %H, 7.86; %N, 17.62. Found: %C, 66.29; %H, 7.78; %N, 17.76.

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