Pyridine → tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate

HRID 1070798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070798
N1C=CC=CC=1.[NH2:7][C:8]1[C:9]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:10][C:11]([CH3:27])=[C:12]([CH3:26])[C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].[CH2:35]([O:37][CH2:38][C:39](Cl)=O)[CH3:36].[OH-].[Na+]>O.ClCCl>[CH2:35]([O:37][CH2:38][C:39]1[N:14]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]2[C:12]([CH3:26])=[C:11]([CH3:27])[N:10]=[C:9]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:8]=2[N:7]=1)[CH3:36]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 84189Ethoxyacetyl chlorideHCID 21973822Tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate

Produkt 1

HCID 21973818tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Using the general method of Example 13 Part D, a pyridine solution of tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (see Example 13 Part C) was treated with ethoxyacetyl chloride (21.81 g, 178 mmol). The crude product was combined with dichloromethane (2 L) and water (2 L). The pH was adjusted to 12 with 50% sodium hydroxide and the mixture was stirred for 30 minutes. The organic phase was separated, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was diluted with heptane and then concentrated to remove residual pyridine. This procedure was repeated several times to provide 64.8 g of tert-butyl 3-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate as a brown tar.

Aufarbeitung

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with heptane
  5. concentrationconcentrated
  6. customto remove residual pyridine

Quellen und Nachweise

ORD-Eintrag
ord-1d358c6756e343d8a6e9e4cbbcc1e8c7
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903113B2

Notizen zur Reaktion

Wird geladen…