반응 #75790

반응 방정식

N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-di-(1,1-dimethylethyl)-4-hydroxybenzamide

→

N1-[2-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-di-(1,1-dimethylethyl)-4-hydroxybenzamide

수율 50.5%

용매

trifluoroacetic acid

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered
2. 2
   기타to remove the catalyst
3. 3
   농축The filtrate was concentrated under vacuum
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   세척The dichloromethane solution was washed twice with 10% sodium hydroxide and with brine
6. 6
   기타dried
7. 7
   농축concentrated under vacuum
8. 8
   기타to provide crude product
9. 9
   기타This material was purified by chromatography
10. 10
    세척eluting with 10% methanol in dichloromethane
11. 11
    기타The resulting oil was triturated with acetonitrile

실험 절차

A solution of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-di-(1,1-dimethylethyl)-4-hydroxybenzamide (0.1 g, 0.19 mmol) in trifluoroacetic acid (15 mL) and platinum oxide (0.1 g) were combined and hydrogenated overnight on a Parr apparatus. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane. The dichloromethane solution was washed twice with 10% sodium hydroxide and with brine, dried and then concentrated under vacuum to provide crude product. This material was purified by chromatography eluting with 10% methanol in dichloromethane. The resulting oil was triturated with acetonitrile to provide 0.05 g of N1-[2-(4-amino-2-butyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-di-(1,1-dimethylethyl)-4-hydroxybenzamide as a white powder, m.p. 208-210° C. Analysis: Calculated for C30H44N6O2+0.1 CF3CO2H: %C, 68.17; %H, 8.35; %N, 15.79; Found: %C, 68.48; %H, 8.29; %N, 16.08.

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