Toluene → tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate

HRID 1265078

Reaktionsgleichung

Reaktionsgleichung von HRID 1265078
[NH2:1][C:2]1[C:3]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:4][C:5]([CH3:20])=[C:6]([CH3:19])[C:7]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[C:28](OCC)(OCC)(OCC)[CH3:29].Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:28][C:29]1[N:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:7]2[C:6]([CH3:19])=[C:5]([CH3:20])[N:4]=[C:3]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:2]=2[N:1]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 66221Triethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 21973843Tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate

Produkt 1

HCID 21973834tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethylcarbamate (43.7 g, 117 mmol), triethyl orthoacetate (22.6 mL; 123 mmol), pyridine hydrochloride (4.4 g) and toluene (440 mL) was heated at reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure to provide a brown oil. The oil was dissolved in ethyl acetate (1 L) and washed with water (2×500 mL). The aqueous washes were combined and extracted with ethyl acetate (2×500 mL). The combined organics were washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide 46.4 g of tert-butyl 2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethylcarbamate as a white solid, m.p. 180-182° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto provide a brown oil
  5. washwashed with water (2×500 mL)
  6. extractionextracted with ethyl acetate (2×500 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b849462e2ee5473cb6a007dbedb6cea1
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545017B1

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