Triethyl orthoacetate → 1-[2,6,7-Trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]eth-2-yl Acetate

HRID 1245895Notes

Reaction equation

HRID 1245895 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[NH2:23])(=[O:3])[CH3:2].[C:24](OCC)(OCC)(OCC)[CH3:25]>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:8]2[C:13]([CH3:14])=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:9]=2[N:23]=[C:24]1[CH3:25])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetateHCID 691934021-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl Acetate

Product 1

HCID 219131671-[2,6,7-Trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]eth-2-yl AcetateYield 98.2%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

1-[(3-Amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]eth-2-yl acetate (10.5 g, 33.29 mmol), toluene (100 mL), pyridine hydrochloride (0.077 g, 0.6659 mmol), and triethyl orthoacetate (9.1 mL, 49.94 mmol) were combined with stirring and the resulting mixture was heated to a gentle reflux (about 95° C.) for 1.5 hours. The reaction was complete. The resulting reaction mixture was concentrated under reduced pressure to white solids, which were dissolved in ethyl acetate. The ethyl acetate solution was washed with water (3×) and brine (2×), dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was triturated with diethyl ether, filtered off, and dried at 60° C. overnight to provide 11.1 g of pure product, which was carried on to the next step.

Workup

  1. temperaturethe resulting mixture was heated to
  2. customThe resulting reaction mixture
  3. concentrationwas concentrated under reduced pressure to white solids, which
  4. dissolutionwere dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water (3×) and brine (2×)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was triturated with diethyl ether
  10. filtrationfiltered off
  11. customdried at 60° C. overnight

Sources & evidence

ORD record
ord-55172a93b75c447ea00a5241a0b0b3b7
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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