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

HRID 1352574Notes

Reaction equation

HRID 1352574 reaction equation
[C:1](OC)(OC)(OC)[CH3:2].[NH2:9][C:10]1[C:11]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:12][C:13]([CH3:31])=[C:14]([CH3:30])[C:15]=1[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].Cl.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:15]2[C:14]([CH3:30])=[C:13]([CH3:31])[N:12]=[C:11]([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 21913447Tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate

Product 1

HCID 21914077tert-butyl 2-[2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethylcarbamateYield 83.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethyl orthoacetate (3.55 mL, 28.27 mmol), tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate (11.21 g, 26.92 mmol), pyridine hydrochloride (1.12 g) and toluene (120 mL) were combined and heated at reflux for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with water (3×100 mL) and brine (1×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 9.85 g of tert-butyl 2-[2-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethylcarbamate.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. washwashed with water (3×100 mL) and brine (1×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66aab8edd9844eff9bcb9813f21a170c
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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