Methyl Acetate → N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}acetamide

HRID 1060681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060681
[C:1]([O-:4])(=O)[CH3:2].[NH4+:5].C(O[CH2:9][C:10]1[N:11]([CH2:28][CH2:29][CH2:30][NH:31]C(=O)OC(C)(C)C)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[C:14](OC3C=CC=CC=3)[C:13]=2[N:27]=1)C.[OH-].[NH4+].[OH-].[Na+].[C:43]([O:46]C)(=O)[CH3:44]>C(Cl)(Cl)Cl>[NH2:5][C:14]1[C:13]2[N:27]=[C:10]([CH2:9][O:4][CH2:1][CH3:2])[N:11]([CH2:28][CH2:29][CH2:30][NH:31][C:43](=[O:46])[CH3:44])[C:12]=2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=1

Komponenten

7

Edukt 5

HCID 6584Methyl AcetateHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 21973818tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate

Produkt 1

HCID 10236680N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Ammonium acetate (500 g) and tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate (35.09 g, 77 mmol) were combined in a 2 L flask. The neck of the flask was stuffed with a wad of paper towels. The reaction mixture was heated with stirring at 150° C. for 27 hours. The reaction mixture was allowed to cool to ambient temperature and then it was placed in an ice bath. Ammonium hydroxide was added until the pH reached 11. Sodium hydroxide (50%) was added until the pH reached 14. The resulting precipitate was isolated by filtration and then dissolved in chloroform (4 L). The chloroform solution was divided into two portions and each was washed with saturated potassium carbonate (2×2 L). The organics were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide 30.3 g of crude product. This material was slurried with methyl acetate to provide 13.7 g of N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}acetamide as a gray solid, m.p. 161.8-162.3° C. Analysis: Calculated for C16H25N5O2: % C, 60.17; % H, 7.89; % N, 21.93; Found: % C, 59.97; % H, 7.70; % N, 22.19. 1H NMR (Bruker 300 MHz, CHCl3-d) δ 4.91 (s, 2H), 4.73 (s, 2H), 4.43 (t, J=8.1 Hz, 2H), 3.59 (q, J=6.8 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 2.47 (s, 3H), 2.45 (s, 3H), 1.94 (p, J=8.1 Hz, 2H), 1.22 (t, J=6.8 Hz, 3H), 1.08 (s, 2H). MS(CI) m/e 278 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto cool to ambient temperature
  3. customit was placed in an ice bath
  4. customThe resulting precipitate was isolated by filtration
  5. washeach was washed with saturated potassium carbonate (2×2 L)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto provide 30.3 g of crude product

Quellen und Nachweise

ORD-Eintrag
ord-8516313d989b46c1945a3b643bac17ca
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525064B1

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