Hydrochloric Acid → N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]acetamide hydrochloride

HRID 1815037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1815037
[C:1]([O-:4])(=O)[CH3:2].[NH4+:5].[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](OC3C=CC=CC=3)[C:10]=2[N:24]=1.[ClH:35]>C(O)(C)C.C(OCC)C>[ClH:35].[NH2:5][C:11]1[C:10]2[N:24]=[C:7]([CH3:6])[N:8]([CH2:25][CH2:26][NH:27][C:1](=[O:4])[CH3:2])[C:9]=2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 21973834tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate

Produkt 1

HCID 22499154N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]acetamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of ammonium acetate (95 g) and tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate (9.5 g) was heated at 160° C. in a sealed tube for 24 hours. The reaction mixture was allowed to cool to ambient temperature and then it was partitioned between water and chloroform. The aqueous layer was made basic (pH 13) with 50% sodium hydroxide and then extracted with chloroform (10×400 mL). The combined organics were dried over magnesium sulfate and then concentrated under reduced pressure to provide a brown solid. The solid was dissolved in warm isopropanol (80 mL) and then combined with 1M hydrochloric acid in diethyl ether (23.7 mL). The resulting precipitate was isolated by filtration, washed with cold isopropanol and diethyl ether, and then dried in a vacuum oven at 80° C. overnight to provide 5.0 g of N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]acetamide hydrochloride as a white solid, m.p.>250° C. Analysis: Calculated for: C13H19N5O.1.00 HCl: % C, 52.43; % H, 6.77; % N, 23.52; Found: % C, 52.25; % H, 6.81; % N, 23.41.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customit was partitioned between water and chloroform
  3. extractionextracted with chloroform (10×400 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a brown solid
  7. customThe resulting precipitate was isolated by filtration
  8. washwashed with cold isopropanol and diethyl ether
  9. customdried in a vacuum oven at 80° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-cd54bb4ab6674592bab14d6ffa8b17fe
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878719B2

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