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

HRID 1815017Notes

Reaction equation

HRID 1815017 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Using the general method of Example 12 Part D, a pyridine solution of tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (see Example 12 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.

Workup

  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

Sources & evidence

ORD record
ord-3f7e74dc10844d9b886f80cf3b6bfacf
Source dataset
uspto-grants-2005_04
Patent number
US06878719B2

Reaction notes

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