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

HRID 47512

Reaktionsgleichung

Reaktionsgleichung von HRID 47512
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][CH2:36][CH2:37][CH3:38])[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:34])[C:19]3[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([OH:29])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=3)[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1>FC(F)(F)C(O)=O.[Pt]=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][CH2:36][CH2:37][CH3:38])[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:34])[C:19]3[CH:24]=[C:23]([C:25]([CH3:27])([CH3:28])[CH3:26])[C:22]([OH:29])=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:20]=3)[C:10]=2[C:9]2[NH:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Komponenten

4

Edukt 1

HCID 12112191N1-[2-(4-amino-2-butyl 1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-di-(1,1-dimethylethyl)-4-hydroxybenzamide

Produkt 1

HCID 22172667N1-[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-hydroxybenzamideAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washThe dichloromethane solution was washed twice with 10% sodium hydroxide and with brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customto provide crude product
  9. customThis material was purified by chromatography
  10. washeluting with 10% methanol in dichloromethane
  11. customThe resulting oil was triturated with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-2a7deb7aaaf94e27b282bb94ce521411
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699878B2

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